1. Introduction to glycobiology
Course Objectives
Learn the basic language of glycobiology
Monosaccharides (vertebrate)
Glycans (oligosaccharide & glycoconjugate basic concepts)
Learn basic glycan functions
Glycans in glycoprotein activity, folding, trafficking
O-GlcNAc-mediated regulation
Glycolipids in membrane recognition & regulation
Proteoglycans in the extracellular matrix
Glycan binding proteins
Learn the basic concepts of glycan biosynthesis
Learn the basic tools of glycomics (analysis)

2. Introduction to glycobiology
Date
Day
Lecture
Faculty
Mar 27
Mon
Saccharides & The Glyco World
Dr. R. Schnaar
Mar 28
Tue
Glycoproteins 1
Dr. N. Zachara
Mar 29
Wed
Glycoproteins 2
Mar 30
Thu
O-GlcNAc
Dr. G. Hart
Mar 31
Fri
Glycolipids and GPI anchors
Apr 3
Hyaluronan and Proteoglycans
Apr 4
Carbohydrate Engineering
Dr. K. Yarema
Apr 5
Protein-Glycan Recognition
Apr 5*
Glycan Binding Protein Functions
Apr 6
Glycomics (Analytical Glycobiology)
Apr 6*
Glycans and Disease

3. Introduction to glycobiology
Course co-directors:
Ronald Schnaar
Natasha Zachara
Lecturers:
Gerald Hart
Kevin Yarema

4. Introduction to glycobiology
Oxford University Press, 2011
Cold Spring Harbor Laboratory Press, Content freely available:
NOTE: 3rd Edition release date June 2017

5. What are:
Glycobiology?
Glycoscience?
Glycomics?

6. Glycobiology
The study of the biological functions, structures, recognition and biosynthesis of glycans (sugar chains, saccharides) in the context of the biological scaffolds to which they are attached (e.g. glycolipids & glycoproteins).

7. Glycoscience Glycobiology & Glycochemistry, including…
- Chemical synthesis Chemoenzymatic synthesis Metabolic engineering Glycomimetics Glycan conformation and structure Material Sciences Plant and bacterial polysaccharides

8. Glycomics - Analytical glycosciences - Glycan bioinformatics
“Glycome” – The total complement of glycans in a cell or organism

9. NOT Carbohydrates as food
Glycobiology is …
NOT Carbohydrates as food
“Carbohydrates in food are important sources of energy. Starch found in plant-derived food such as pasta ....”
Berg, Tymoczko & Stryer (2006) Biochemistry, Sixth Edition, W.H. Freeman, New York

10. Glycobiology is NOT “a” post-translational modification
Glycobiology is NOT “a” post-translational modification... it is thousands
Combinatorial linkage position, orientation and branching provide the potential for thousands* of different glycan structures – functional diversity
Glycans may be larger and more diverse than their (protein) carriers
A glycan’s function can supersede that of its (protein) carrier
1-2% of the human genome is devoted to glycosylation
Modified from faculty/hougland.html
Cummings RD (2009) Molecular BioSystems 5, 1087
*Glycoproteins and glycolipids may contain ~3000 glycan determinants with an additional ~4000 theoretical petasaccharide sequeces in glycosaminoglycans

11. Glycobiology is … NOT a “decoration”
Zolla-Pazner (2004) Nature Reviews Immunology 4, 199
Guillaume et al (2016) Cell 165:813

12. CD59, a complement defense glycoprotein
Proteins typically fold inward, whereas glycans spread out in space
3 kDa N-linked glycan
20 kDa protein
1 kDa O-linked glycan
“naked” CD59, Huang et al (2007)
Acta Crystallographica 63, 714
1.5 kDa GPI anchor
CD59, a complement defense glycoprotein
Rudd et al (1997) J Biol Chem 272, 7229

13. The mammalian cell surface ?
Martinez-Palomo, A., et al. Cancer Res. 29, , 1969
The “glycocalyx” revealed (glycans stained with ruthinium red)
intracellular
fibroblast
extracellular
lipid bilayer
intracellular
fibroblast
extracellular
lipid bilayer
wiki/Plasma_membrane
Krijnse Locker J. & Schmid S.L. PLoS Biol 11, e , 2013
“Every eukaryotic cell is covered with a dense and complex array of glycans.” … in fact…
“Evolution has failed to generate a [single] living cell devoid of surface glycosylation” - A. Varki

14. What if a MAJOR cell component was invisible by standard microscopy?
Light microscopy micrograph of Cryptococcus neoformans capsule delineated by India ink. The inner circle represents the fungal cell, with the wide outer circle being the capsule.
Steenbergen et al. (2003) Microbes and Infection 5:667
Light microscopy micrograph of Cryptococcus neoformans
Steenbergen et al. (2003) Microbes and Infection 5:667
Scanning electron microscopy of C. neoformans yeast cells.
Van Duin et al. (2004) Antimicrobial Agents and Chemotherapy 48:2014

15. Each prokaryote carries a surface glycan coat
Electron microscopic thin section of Escherichia coli K1
Amako et al. (1988) J Bacteriol 170:4960
Electron microscopic thin section of Klebsiella pneumoniae
Amako et al. (1988) J Bacteriol 170:4960

16. Tropical Forest Canopy
“Evolution has failed to generate a living cell devoid of surface glycosylation” - A. Varki
Cohen & Varki (2010) OMICS 4:455

17. Real image textbook image
The Cell Surface
Real image textbook image
lipid bilayer
fibroblast
intracellular
Martinez-Palomo, A., et al. Cancer Res. 29, , 1969
Among their diverse functions, glycans …
encode intermolecular and cell-cell recognition
regulate the activities of proteins (enzymes, ion channels, receptors)
Define biophysical space (large, hydrated)

18. Glycobiology = Language*
*semiotics: the theory of signs and symbols
Rosetta Stone, British Museum

19. Saccharides Carbohydrates: The language of glycobiology
The glycosidic bond and glycan nomenclature
Major vertebrate glycan classes

20. Saccharides Carbohydrates: The language of glycobiology
The glycosidic bond and glycan nomenclature
Major vertebrate glycan classes

21. (CH2O)n = “carbo” “hydrate”
Carbohydrates – the building blocks of Glycobiology
(CH2O)n = “carbo” “hydrate”
Generalized Ketose
Generalized Aldose

22. glucose
fructose

23. Monosaccharide structural identity is all about stereochemistry
Generalized Aldose
Monosaccharide structural identity is all about stereochemistry
Enantiomers:
mirror images of each other that are not superimposable.
Diastereomers:
stereoisomers that are not enantiomers.

24. Fischer projection
D-glyceraldehyde

25. Enantiomers * * D-glyceraldehyde L-glyceraldehyde *
Highest numbered asymmetric carbon = reference carbon

26. Diasteriomers * * *
Highest numbered asymmetric carbon = reference carbon

27. diasteriomers & enantiomers
Enantiomers & Diasteriomers * *
carbons
asymmetric carbons
diaster- iomers
diasteriomers & enantiomers 3 1 2 4 5 8 6 16 * * *
Highest numbered asymmetric carbon = reference carbon

28. Essentials of Glycobiology*
* epimers: differ at a single stereogenic center
Essentials of Glycobiology
Second Edition

29. Monosaccharides equilibrate between open chain and ring forms
Monosaccharides equilibrate between open chain and ring forms. Two ring forms (anomeric configurations) are possible, α and β
α-D-glucose
β-D-glucose
D-glucose
Taylor & Drickamer (2011) Introduction to Glycobiology, 3rd edition

30. Monosaccharide conformation – Chair configuations
Taylor & Drickamer (2006) Introduction to Glycobiology, 2nd edition

31. Nearly all vertebrate glycans are built from only 9 sugars:
3 hexoses
Glucose
Mannose
Galactose
2 N-acetylhexosamines
N-acetylglucosamine
N-acetylgalactosamine
xylose
glucuronic acid
sialic acid
L-fucose
*all D configuation except fucose

32. Seven eukaryotic sugars and their relationship to glucose
Taylor & Drickamer (2011) Introduction to Glycobiology, 3rd edition

33. Two important terminal eukaryotic sugars
Taylor & Drickamer (2011) Introduction to Glycobiology, 3rd edition

34. Glycan properties for molecular recognition and binding energy
Glucose
Galactose
Mannose
Sialic Acid

35. Saccharides Carbohydrates: The language of glycobiology
The glycosidic bond and glycan nomenclature
Major vertebrate glycan classes

36. Saccharides Carbohydrates: The language of glycobiology
The glycosidic bond and glycan nomenclature
Major vertebrate glycan classes

37. Glycosidic bonds link sugars together
(lactose)
CCRC
When a glycosidic bond is formed the anomeric configuration is “locked”
Taylor & Drickamer (2011) Introduction to Glycobiology, 3rd edition

38. Nomenclature:
-Name the non-reducing (left-most) sugar (Gal) -Name the anomeric configuration (β) -Name the anomeric carbon number (1) -Name the substituted carbon number (4) -Name the substituted sugar (Glc)
RESULT: Gal β1-4 Glc
Taylor & Drickamer (2011) Introduction to Glycobiology, 3rd edition

39. Nomenclature: Branches are placed in parentheses
NeuAc α2-3 Gal β1-4 (Fuc α1-3) GlcNAc

40. Varki et al. (2009) Proteomics. 9:5398

41. Oligosaccharides: Molecular diversity of glycans
Polypeptides
Glycans
Building blocks
amino acids
monosaccharides
Number of different monomers
20 common
9 common
Linkage sites per monomer 1
3-4
Possible linkage configurations 2
Possible homodimer structures
6-8
Linkage modes
linear
linear or branched

42. Three different amino acids (Ala, Ser, Tyr) – 6 structures Ala-Ser-Tyr   
Ala-Ser-Tyr
Ala-Tyr-Ser
Ser-Ala-Tyr
Ser-Tyr-Ala
Tyr-Ala-Ser
Tyr-Ser-Ala
Three different sugars (Glc, Gal, Man) – 1,056 structures …

43. Man a1-4 Gal a1-3 Glc b1 Man a1-6 Gal a1-3 Glc b1
 Gal a1-2 Glc a1-2 Man a1-
Gal a1-3 Glc a1-6 Man b1-
Gal a1-4 Man b1-4 Glc a1-
Man a1-6 Glc a1-3 Gal a1-
Man b1-2 Glc b1-2 Gal b1-
Man b1-3 Gal b1-6 Glc a1-
Glc b1-4 Man a1-4 Gal a1-
Glc b1-6 Man b1-3 Gal b1-
Glc a1-2 Gal a1-3 Man b1-
Gal a1-6 (Glc b1-2) Man a1-
Gal a1-2 (Man b1-6) Glc a1-
Glc b1-4 (Man a1-3) Gal a1-
Gal a1-3 Glc a1-2 Man a1-
Gal a1-4 Glc a1-6 Man b1-
Gal a1-6 Man b1-4 Glc a1-
Man b1-2 Glc a1-3 Gal a1-
Man b1-3 Glc b1-2 Gal b1-
Man b1-4 Gal b1-6 Glc a1-
Glc b1-6 Man a1-4 Gal a1-
Glc a1-2 Man b1-4 Gal b1-
Glc a1-3 Gal a1-3 Man b1-
Gal a1-6 (Glc b1-3) Man a1-
Gal a1-3 (Man b1-2) Glc a1-
Glc b1-4 (Man a1-6) Gal a1-
Gal a1-4 Glc a1-2 Man a1-
Gal a1-6 Glc a1-6 Man b1-
Gal b1-2 Man b1-4 Glc a1-
Man b1-3 Glc a1-3 Gal a1-
Man b1-4 Glc b1-2 Gal b1-
Man b1-6 Gal b1-6 Glc a1-
Glc a1-2 Man a1-6 Gal a1-
Glc a1-3 Man b1-4 Gal b1-
Glc a1-4 Gal a1-3 Man b1-
Gal a1-6 (Glc b1-4) Man a1-
Gal a1-3 (Man b1-4) Glc a1-
Glc b1-6 (Man a1-2) Gal a1-
Gal a1-6 Glc a1-2 Man a1-
Gal b1-2 Glc a1-6 Man b1-
Gal b1-3 Man b1-4 Glc a1-
Man b1-4 Glc a1-3 Gal a1-
Man b1-6 Glc b1-2 Gal b1-
Man a1-2 Gal a1-2 Glc b1
Glc a1-3 Man a1-6 Gal a1-
Glc a1-4 Man b1-4 Gal b1-
Glc a1-6 Gal a1-3 Man b1-
Gal b1-2 (Glc b1-3) Man a1-
Gal a1-3 (Man b1-6) Glc a1-
Glc b1-6 (Man a1-3) Gal a1-
Gal b1-2 Glc a1-2 Man a1-
Gal b1-3 Glc a1-6 Man b1-
Gal b1-4 Man b1-4 Glc a1-
Man b1-6 Glc a1-3 Gal a1-
Man a1-2 Glc b1-3 Gal b1-
Man a1-3 Gal a1-2 Glc b1
Glc a1-4 Man a1-6 Gal a1-
Glc a1-6 Man b1-4 Gal b1-
Glc b1-2 Gal a1-3 Man b1-
Gal b1-2 (Glc b1-4) Man a1-
Gal a1-4 (Man b1-2) Glc a1-
Glc b1-6 (Man a1-4) Gal a1-
Gal b1-3 Glc a1-2 Man a1-
Gal b1-4 Glc a1-6 Man b1-
Gal b1-6 Man b1-4 Glc a1-
Man a1-2 Glc a1-4 Gal a1-
Man a1-3 Glc b1-3 Gal b1-
Man a1-4 Gal a1-2 Glc b1
Glc a1-6 Man a1-6 Gal a1-
Glc b1-2 Man b1-4 Gal b1-
Glc b1-3 Gal a1-3 Man b1-
Gal b1-2 (Glc b1-6) Man a1-
Gal a1-4 (Man b1-3) Glc a1-
Glc a1-2 (Man b1-3) Gal a1-
Gal b1-4 Glc a1-2 Man a1-
Gal b1-6 Glc a1-6 Man b1-
Gal a1-2 Man b1-6 Glc a1-
Man a1-3 Glc a1-4 Gal a1-
Man a1-4 Glc b1-3 Gal b1-
Man a1-6 Gal a1-2 Glc b1
Glc b1-2 Man a1-6 Gal a1-
Glc b1-3 Man b1-4 Gal b1-
Glc b1-4 Gal a1-3 Man b1-
Gal b1-3 (Glc b1-2) Man a1-
Gal a1-4 (Man b1-6) Glc a1-
Glc a1-2 (Man b1-4) Gal a1-
Gal b1-6 Glc a1-2 Man a1-
Gal a1-2 Glc b1-2 Man b1-
Gal a1-3 Man b1-6 Glc a1-
Man a1-4 Glc a1-4 Gal a1-
Man a1-6 Glc b1-3 Gal b1-
Man b1-2 Gal a1-2 Glc b1
Glc b1-3 Man a1-6 Gal a1-
Glc b1-4 Man b1-4 Gal b1-
Glc b1-6 Gal a1-3 Man b1-
Gal b1-3 (Glc b1-4) Man a1-
Gal a1-6 (Man b1-2) Glc a1-
Glc a1-2 (Man b1-6) Gal a1-
Gal a1-2 Glc a1-3 Man a1-
Gal a1-3 Glc b1-2 Man b1-
Gal a1-4 Man b1-6 Glc a1-
Man a1-6 Glc a1-4 Gal a1-
Man b1-2 Glc b1-3 Gal b1-
Man b1-3 Gal a1-2 Glc b1
Glc b1-4 Man a1-6 Gal a1-
Glc b1-6 Man b1-4 Gal b1-
Glc a1-2 Gal a1-4 Man b1-
Gal b1-3 (Glc b1-6) Man a1-
Gal a1-6 (Man b1-3) Glc a1-
Glc a1-3 (Man b1-2) Gal a1-
Gal a1-3 Glc a1-3 Man a1-
Gal a1-4 Glc b1-2 Man b1-
Gal a1-6 Man b1-6 Glc a1-
Man b1-2 Glc a1-4 Gal a1-
Man b1-3 Glc b1-3 Gal b1-
Man b1-4 Gal a1-2 Glc b1
Glc b1-6 Man a1-6 Gal a1-
Glc a1-2 Man b1-6 Gal b1-
Glc a1-3 Gal a1-4 Man b1-
Gal b1-4 (Glc b1-2) Man a1-
Gal a1-6 (Man b1-4) Glc a1-
Glc a1-3 (Man b1-4) Gal a1-
Gal a1-4 Glc a1-3 Man a1-
Gal a1-6 Glc b1-2 Man b1-
Gal b1-2 Man b1-6 Glc a1-
Man b1-3 Glc a1-4 Gal a1-
Man b1-4 Glc b1-3 Gal b1-
Man b1-6 Gal a1-2 Glc b1
Glc a1-2 Man b1-2 Gal a1-
Glc a1-3 Man b1-6 Gal b1-
Glc a1-4 Gal a1-4 Man b1-
Gal b1-4 (Glc b1-3) Man a1-
Gal b1-2 (Man b1-3) Glc a1-
Glc a1-3 (Man b1-6) Gal a1-
Gal a1-6 Glc a1-3 Man a1-
Gal b1-2 Glc b1-2 Man b1-
Gal b1-3 Man b1-6 Glc a1-
Man b1-4 Glc a1-4 Gal a1-
Man b1-6 Glc b1-3 Gal b1-
Man a1-2 Gal a1-3 Glc b1
Glc a1-3 Man b1-2 Gal a1-
Glc a1-4 Man b1-6 Gal b1-
Glc a1-6 Gal a1-4 Man b1-
Gal b1-4 (Glc b1-6) Man a1-
Gal b1-2 (Man b1-4) Glc a1-
Glc a1-4 (Man b1-2) Gal a1-
Gal b1-2 Glc a1-3 Man a1-
Gal b1-3 Glc b1-2 Man b1-
Gal b1-4 Man b1-6 Glc a1-
Man b1-6 Glc a1-4 Gal a1-
Man a1-2 Glc b1-4 Gal b1-
Man a1-3 Gal a1-3 Glc b1
Glc a1-4 Man b1-2 Gal a1-
Glc a1-6 Man b1-6 Gal b1-
Glc b1-2 Gal a1-4 Man b1-
Gal b1-6 (Glc b1-2) Man a1-
Gal b1-2 (Man b1-6) Glc a1-
Glc a1-4 (Man b1-3) Gal a1-
Gal b1-3 Glc a1-3 Man a1-
Gal b1-4 Glc b1-2 Man b1-
Gal b1-6 Man b1-6 Glc a1-
Man a1-2 Glc a1-6 Gal a1-
Man a1-3 Glc b1-4 Gal b1-
Man a1-4 Gal a1-3 Glc b1
Glc a1-6 Man b1-2 Gal a1-
Glc b1-2 Man b1-6 Gal b1-
Glc b1-3 Gal a1-4 Man b1-
Gal b1-6 (Glc b1-3) Man a1-
Gal b1-3 (Man b1-2) Glc a1-
Glc a1-4 (Man b1-6) Gal a1-
Gal b1-4 Glc a1-3 Man a1-
Gal b1-6 Glc b1-2 Man b1-
Gal a1-2 Man a1-2 Glc b1-
Man a1-3 Glc a1-6 Gal a1-
Man a1-4 Glc b1-4 Gal b1-
Man a1-6 Gal a1-3 Glc b1
Glc b1-2 Man b1-2 Gal a1-
Glc b1-3 Man b1-6 Gal b1-
Glc b1-4 Gal a1-4 Man b1-
Gal b1-6 (Glc b1-4) Man a1-
Gal b1-3 (Man b1-4) Glc a1-
Glc a1-6 (Man b1-2) Gal a1-
Gal b1-6 Glc a1-3 Man a1-
Gal a1-2 Glc b1-3 Man b1-
Gal a1-3 Man a1-2 Glc b1-
Man a1-4 Glc a1-6 Gal a1-
Man a1-6 Glc b1-4 Gal b1-
Man b1-2 Gal a1-3 Glc b1
Glc b1-3 Man b1-2 Gal a1-
Glc b1-4 Man b1-6 Gal b1-
Glc b1-6 Gal a1-4 Man b1-
Gal a1-2 (Glc a1-3) Man b1-
Gal b1-3 (Man b1-6) Glc a1-
Glc a1-6 (Man b1-3) Gal a1-
Gal a1-2 Glc a1-4 Man a1-
Gal a1-3 Glc b1-3 Man b1-
Gal a1-4 Man a1-2 Glc b1-
Man a1-6 Glc a1-6 Gal a1-
Man b1-2 Glc b1-4 Gal b1-
Man b1-3 Gal a1-3 Glc b1
Glc b1-4 Man b1-2 Gal a1-
Glc b1-6 Man b1-6 Gal b1-
Glc a1-2 Gal a1-6 Man b1-
Gal a1-2 (Glc a1-4) Man b1-
Gal b1-4 (Man b1-2) Glc a1-
Glc a1-6 (Man b1-4) Gal a1-
Gal a1-3 Glc a1-4 Man a1-
Gal a1-4 Glc b1-3 Man b1-
Gal a1-6 Man a1-2 Glc b1-
Man b1-2 Glc a1-6 Gal a1-
Man b1-3 Glc b1-4 Gal b1-
Man b1-4 Gal a1-3 Glc b1
Glc b1-6 Man b1-2 Gal a1-
Glc a1-2 Gal a1-2 Man a1-
Glc a1-3 Gal a1-6 Man b1-
Gal a1-2 (Glc a1-6) Man b1-
Gal b1-4 (Man b1-3) Glc a1-
Glc b1-2 (Man b1-3) Gal a1-
Gal a1-4 Glc a1-4 Man a1-
Gal a1-6 Glc b1-3 Man b1-
Gal b1-2 Man a1-2 Glc b1-
Man b1-3 Glc a1-6 Gal a1-
Man b1-4 Glc b1-4 Gal b1-
Man b1-6 Gal a1-3 Glc b1
Glc a1-2 Man b1-3 Gal a1-
Glc a1-3 Gal a1-2 Man a1-
Glc a1-4 Gal a1-6 Man b1-
Gal a1-3 (Glc a1-2) Man b1-
Gal b1-4 (Man b1-6) Glc a1-
Glc b1-2 (Man b1-4) Gal a1-
Gal a1-6 Glc a1-4 Man a1-
Gal b1-2 Glc b1-3 Man b1-
Gal b1-3 Man a1-2 Glc b1-
Man b1-4 Glc a1-6 Gal a1-
Man b1-6 Glc b1-4 Gal b1-
Man a1-2 Gal a1-4 Glc b1
Glc a1-3 Man b1-3 Gal a1-
Glc a1-4 Gal a1-2 Man a1-
Glc a1-6 Gal a1-6 Man b1-
Gal a1-3 (Glc a1-4) Man b1-
Gal b1-6 (Man b1-2) Glc a1-
Glc b1-2 (Man b1-6) Gal a1-
Gal b1-2 Glc a1-4 Man a1-
Gal b1-3 Glc b1-3 Man b1-
Gal b1-4 Man a1-2 Glc b1-
Man b1-6 Glc a1-6 Gal a1-
Man a1-2 Glc b1-6 Gal b1-
Man a1-3 Gal a1-4 Glc b1
Glc a1-4 Man b1-3 Gal a1-
Glc a1-6 Gal a1-2 Man a1-
Glc b1-2 Gal a1-6 Man b1-
Gal a1-3 (Glc a1-6) Man b1-
Gal b1-6 (Man b1-3) Glc a1-
Glc b1-3 (Man b1-2) Gal a1-
Gal b1-3 Glc a1-4 Man a1-
Gal b1-4 Glc b1-3 Man b1-
Gal b1-6 Man a1-2 Glc b1-
Man a1-2 Glc b1-2 Gal a1-
Man a1-3 Glc b1-6 Gal b1-
Man a1-4 Gal a1-4 Glc b1
Glc a1-6 Man b1-3 Gal a1-
Glc b1-2 Gal a1-2 Man a1-
Glc b1-3 Gal a1-6 Man b1-
Gal a1-4 (Glc a1-2) Man b1-
Gal b1-6 (Man b1-4) Glc a1-
Glc b1-3 (Man b1-4) Gal a1-
Gal b1-4 Glc a1-4 Man a1-
Gal b1-6 Glc b1-3 Man b1-
Gal a1-2 Man a1-3 Glc b1-
Man a1-3 Glc b1-2 Gal a1-
Man a1-4 Glc b1-6 Gal b1-
Man a1-6 Gal a1-4 Glc b1
Glc b1-2 Man b1-3 Gal a1-
Glc b1-3 Gal a1-2 Man a1-
Glc b1-4 Gal a1-6 Man b1-
Gal a1-4 (Glc a1-3) Man b1-
Gal a1-2 (Man a1-3) Glc b1-
Glc b1-3 (Man b1-6) Gal a1-
Gal b1-6 Glc a1-4 Man a1-
Gal a1-2 Glc b1-4 Man b1-
Gal a1-3 Man a1-3 Glc b1-
Man a1-4 Glc b1-2 Gal a1-
Man a1-6 Glc b1-6 Gal b1-
Man b1-2 Gal a1-4 Glc b1
Glc b1-3 Man b1-3 Gal a1-
Glc b1-4 Gal a1-2 Man a1-
Glc b1-6 Gal a1-6 Man b1-
Gal a1-4 (Glc a1-6) Man b1-
Gal a1-2 (Man a1-4) Glc b1-
Glc b1-4 (Man b1-2) Gal a1-
Gal a1-2 Glc a1-6 Man a1-
Gal a1-3 Glc b1-4 Man b1-
Gal a1-4 Man a1-3 Glc b1-
Man a1-6 Glc b1-2 Gal a1-
Man b1-2 Glc b1-6 Gal b1-
Man b1-3 Gal a1-4 Glc b1
Glc b1-4 Man b1-3 Gal a1-
Glc b1-6 Gal a1-2 Man a1-
Glc a1-2 Gal b1-2 Man b1-
Gal a1-6 (Glc a1-2) Man b1-
Gal a1-2 (Man a1-6) Glc b1-
Glc b1-4 (Man b1-3) Gal a1-
Gal a1-3 Glc a1-6 Man a1-
Gal a1-4 Glc b1-4 Man b1-
Gal a1-6 Man a1-3 Glc b1-
Man b1-2 Glc b1-2 Gal a1-
Man b1-3 Glc b1-6 Gal b1-
Man b1-4 Gal a1-4 Glc b1
Glc b1-6 Man b1-3 Gal a1-
Glc a1-2 Gal a1-3 Man a1-
Glc a1-3 Gal b1-2 Man b1-
Gal a1-6 (Glc a1-3) Man b1-
Gal a1-3 (Man a1-2) Glc b1-
Glc b1-4 (Man b1-6) Gal a1-
Gal a1-4 Glc a1-6 Man a1-
Gal a1-6 Glc b1-4 Man b1-
Gal b1-2 Man a1-3 Glc b1-
Man b1-3 Glc b1-2 Gal a1-
Man b1-4 Glc b1-6 Gal b1-
Man b1-6 Gal a1-4 Glc b1
Glc a1-2 Man b1-4 Gal a1-
Glc a1-3 Gal a1-3 Man a1-
Glc a1-4 Gal b1-2 Man b1-
Gal a1-6 (Glc a1-4) Man b1-
Gal a1-3 (Man a1-4) Glc b1-
Glc b1-6 (Man b1-2) Gal a1-
Gal a1-6 Glc a1-6 Man a1-
Gal b1-2 Glc b1-4 Man b1-
Gal b1-3 Man a1-3 Glc b1-
Man b1-4 Glc b1-2 Gal a1-
Man b1-6 Glc b1-6 Gal b1-
Man a1-2 Gal a1-6 Glc b1
Glc a1-3 Man b1-4 Gal a1-
Glc a1-4 Gal a1-3 Man a1-
Glc a1-6 Gal b1-2 Man b1-
Gal b1-2 (Glc a1-3) Man b1-
Gal a1-3 (Man a1-6) Glc b1-
Glc b1-6 (Man b1-3) Gal a1-
Gal b1-2 Glc a1-6 Man a1-
Gal b1-3 Glc b1-4 Man b1-
Gal b1-4 Man a1-3 Glc b1-
Man b1-6 Glc b1-2 Gal a1-
Man a1-2 Gal a1-2 Glc a1-
Man a1-3 Gal a1-6 Glc b1
Glc a1-4 Man b1-4 Gal a1-
Glc a1-6 Gal a1-3 Man a1-
Glc b1-2 Gal b1-2 Man b1-
Gal b1-2 (Glc a1-4) Man b1-
Gal a1-4 (Man a1-2) Glc b1-
Glc b1-6 (Man b1-4) Gal a1-
Gal b1-3 Glc a1-6 Man a1-
Gal b1-4 Glc b1-4 Man b1-
Gal b1-6 Man a1-3 Glc b1-
Man a1-2 Glc b1-3 Gal a1-
Man a1-3 Gal a1-2 Glc a1-
Man a1-4 Gal a1-6 Glc b1
Glc a1-6 Man b1-4 Gal a1-
Glc b1-2 Gal a1-3 Man a1-
Glc b1-3 Gal b1-2 Man b1-
Gal b1-2 (Glc a1-6) Man b1-
Gal a1-4 (Man a1-3) Glc b1-
Glc a1-2 (Man a1-3) Gal b1-
Gal b1-4 Glc a1-6 Man a1-
Gal b1-6 Glc b1-4 Man b1-
Gal a1-2 Man a1-4 Glc b1-
Man a1-3 Glc b1-3 Gal a1-
Man a1-4 Gal a1-2 Glc a1-
Man a1-6 Gal a1-6 Glc b1
Glc b1-2 Man b1-4 Gal a1-
Glc b1-3 Gal a1-3 Man a1-
Glc b1-4 Gal b1-2 Man b1-
Gal b1-3 (Glc a1-2) Man b1-
Gal a1-4 (Man a1-6) Glc b1-
Glc a1-2 (Man a1-4) Gal b1-
Gal b1-6 Glc a1-6 Man a1-
Gal a1-2 Glc b1-6 Man b1-
Gal a1-3 Man a1-4 Glc b1-
Man a1-4 Glc b1-3 Gal a1-
Man a1-6 Gal a1-2 Glc a1-
Man b1-2 Gal a1-6 Glc b1
Glc b1-3 Man b1-4 Gal a1-
Glc b1-4 Gal a1-3 Man a1-
Glc b1-6 Gal b1-2 Man b1-
Gal b1-3 (Glc a1-4) Man b1-
Gal a1-6 (Man a1-2) Glc b1-
Glc a1-2 (Man a1-6) Gal b1-
Gal a1-2 Glc b1-2 Man a1-
Gal a1-3 Glc b1-6 Man b1-
Gal a1-4 Man a1-4 Glc b1-
Man a1-6 Glc b1-3 Gal a1-
Man b1-2 Gal a1-2 Glc a1-
Man b1-3 Gal a1-6 Glc b1
Glc b1-4 Man b1-4 Gal a1-
Glc b1-6 Gal a1-3 Man a1-
Glc a1-2 Gal b1-3 Man b1-
Gal b1-3 (Glc a1-6) Man b1-
Gal a1-6 (Man a1-3) Glc b1-
Glc a1-3 (Man a1-2) Gal b1-
Gal a1-3 Glc b1-2 Man a1-
Gal a1-4 Glc b1-6 Man b1-
Gal a1-6 Man a1-4 Glc b1-
Man b1-2 Glc b1-3 Gal a1-
Man b1-3 Gal a1-2 Glc a1-
Man b1-4 Gal a1-6 Glc b1
Glc b1-6 Man b1-4 Gal a1-
Glc a1-2 Gal a1-4 Man a1-
Glc a1-3 Gal b1-3 Man b1-
Gal b1-4 (Glc a1-2) Man b1-
Gal a1-6 (Man a1-4) Glc b1-
Glc a1-3 (Man a1-4) Gal b1-
Gal a1-4 Glc b1-2 Man a1-
Gal a1-6 Glc b1-6 Man b1-
Gal b1-2 Man a1-4 Glc b1-
Man b1-3 Glc b1-3 Gal a1-
Man b1-4 Gal a1-2 Glc a1-
Man b1-6 Gal a1-6 Glc b1
Glc a1-2 Man b1-6 Gal a1-
Glc a1-3 Gal a1-4 Man a1-
Glc a1-4 Gal b1-3 Man b1-
Gal b1-4 (Glc a1-3) Man b1-
Gal b1-2 (Man a1-3) Glc b1-
Glc a1-3 (Man a1-6) Gal b1-
Gal a1-6 Glc b1-2 Man a1-
Gal b1-2 Glc b1-6 Man b1-
Gal b1-3 Man a1-4 Glc b1-
Man b1-4 Glc b1-3 Gal a1-
Man b1-6 Gal a1-2 Glc a1-
Man a1-2 Gal b1-2 Glc b1
Glc a1-3 Man b1-6 Gal a1-
Glc a1-4 Gal a1-4 Man a1-
Glc a1-6 Gal b1-3 Man b1-
Gal b1-4 (Glc a1-6) Man b1-
Gal b1-2 (Man a1-4) Glc b1-
Glc a1-4 (Man a1-2) Gal b1-
Gal b1-2 Glc b1-2 Man a1-
Gal b1-3 Glc b1-6 Man b1-
Gal b1-4 Man a1-4 Glc b1-
Man b1-6 Glc b1-3 Gal a1-
Man a1-2 Gal a1-3 Glc a1-
Man a1-3 Gal b1-2 Glc b1
Glc a1-4 Man b1-6 Gal a1-
Glc a1-6 Gal a1-4 Man a1-
Glc b1-2 Gal b1-3 Man b1-
Gal b1-6 (Glc a1-2) Man b1-
Gal b1-2 (Man a1-6) Glc b1-
Glc a1-4 (Man a1-3) Gal b1-
Gal b1-3 Glc b1-2 Man a1-
Gal b1-4 Glc b1-6 Man b1-
Gal b1-6 Man a1-4 Glc b1-
Man a1-2 Glc b1-4 Gal a1-
Man a1-3 Gal a1-3 Glc a1-
Man a1-4 Gal b1-2 Glc b1
Glc a1-6 Man b1-6 Gal a1-
Glc b1-2 Gal a1-4 Man a1-
Glc b1-3 Gal b1-3 Man b1-
Gal b1-6 (Glc a1-3) Man b1-
Gal b1-3 (Man a1-2) Glc b1-
Glc a1-4 (Man a1-6) Gal b1-
Gal b1-4 Glc b1-2 Man a1-
Gal b1-6 Glc b1-6 Man b1-
Gal a1-2 Man a1-6 Glc b1-
Man a1-3 Glc b1-4 Gal a1-
Man a1-4 Gal a1-3 Glc a1-
Man a1-6 Gal b1-2 Glc b1
Glc b1-2 Man b1-6 Gal a1-
Glc b1-3 Gal a1-4 Man a1-
Glc b1-4 Gal b1-3 Man b1-
Gal b1-6 (Glc a1-4) Man b1-
Gal b1-3 (Man a1-4) Glc b1-
Glc a1-6 (Man a1-2) Gal b1-
Gal b1-6 Glc b1-2 Man a1-
Gal a1-2 Man a1-2 Glc a1-
Gal a1-3 Man a1-6 Glc b1-
Man a1-4 Glc b1-4 Gal a1-
Man a1-6 Gal a1-3 Glc a1-
Man b1-2 Gal b1-2 Glc b1
Glc b1-3 Man b1-6 Gal a1-
Glc b1-4 Gal a1-4 Man a1-
Glc b1-6 Gal b1-3 Man b1-
Gal a1-2 (Glc b1-3) Man b1-
Gal b1-3 (Man a1-6) Glc b1-
Glc a1-6 (Man a1-3) Gal b1-
Gal a1-2 Glc b1-3 Man a1-
Gal a1-3 Man a1-2 Glc a1-
Gal a1-4 Man a1-6 Glc b1-
Man a1-6 Glc b1-4 Gal a1-
Man b1-2 Gal a1-3 Glc a1-
Man b1-3 Gal b1-2 Glc b1
Glc b1-4 Man b1-6 Gal a1-
Glc b1-6 Gal a1-4 Man a1-
Glc a1-2 Gal b1-4 Man b1-
Gal a1-2 (Glc b1-4) Man b1-
Gal b1-4 (Man a1-2) Glc b1-
Glc a1-6 (Man a1-4) Gal b1-
Gal a1-3 Glc b1-3 Man a1-
Gal a1-4 Man a1-2 Glc a1-
Gal a1-6 Man a1-6 Glc b1-
Man b1-2 Glc b1-4 Gal a1-
Man b1-3 Gal a1-3 Glc a1-
Man b1-4 Gal b1-2 Glc b1
Glc b1-6 Man b1-6 Gal a1-
Glc a1-2 Gal a1-6 Man a1-
Glc a1-3 Gal b1-4 Man b1-
Gal a1-2 (Glc b1-6) Man b1-
Gal b1-4 (Man a1-3) Glc b1-
Glc b1-2 (Man a1-3) Gal b1-
Gal a1-4 Glc b1-3 Man a1-
Gal a1-6 Man a1-2 Glc a1-
Gal b1-2 Man a1-6 Glc b1-
Man b1-3 Glc b1-4 Gal a1-
Man b1-4 Gal a1-3 Glc a1-
Man b1-6 Gal b1-2 Glc b1
Glc a1-2 Man a1-2 Gal b1-
Glc a1-3 Gal a1-6 Man a1-
Glc a1-4 Gal b1-4 Man b1-
Gal a1-3 (Glc b1-2) Man b1-
Gal b1-4 (Man a1-6) Glc b1-
Glc b1-2 (Man a1-4) Gal b1-
Gal a1-6 Glc b1-3 Man a1-
Gal b1-2 Man a1-2 Glc a1-
Gal b1-3 Man a1-6 Glc b1-
Man b1-4 Glc b1-4 Gal a1-
Man b1-6 Gal a1-3 Glc a1-
Man a1-2 Gal b1-3 Glc b1
Glc a1-3 Man a1-2 Gal b1-
Glc a1-4 Gal a1-6 Man a1-
Glc a1-6 Gal b1-4 Man b1-
Gal a1-3 (Glc b1-4) Man b1-
Gal b1-6 (Man a1-2) Glc b1-
Glc b1-2 (Man a1-6) Gal b1-
Gal b1-2 Glc b1-3 Man a1-
Gal b1-3 Man a1-2 Glc a1-
Gal b1-4 Man a1-6 Glc b1-
Man b1-6 Glc b1-4 Gal a1-
Man a1-2 Gal a1-4 Glc a1-
Man a1-3 Gal b1-3 Glc b1
Glc a1-4 Man a1-2 Gal b1-
Glc a1-6 Gal a1-6 Man a1-
Glc b1-2 Gal b1-4 Man b1-
Gal a1-3 (Glc b1-6) Man b1-
Gal b1-6 (Man a1-3) Glc b1-
Glc b1-3 (Man a1-2) Gal b1-
Gal b1-3 Glc b1-3 Man a1-
Gal b1-4 Man a1-2 Glc a1-
Gal b1-6 Man a1-6 Glc b1-
Man a1-2 Glc b1-6 Gal a1-
Man a1-3 Gal a1-4 Glc a1-
Man a1-4 Gal b1-3 Glc b1
Glc a1-6 Man a1-2 Gal b1-
Glc b1-2 Gal a1-6 Man a1-
Glc b1-3 Gal b1-4 Man b1-
Gal a1-4 (Glc b1-2) Man b1-
Gal b1-6 (Man a1-4) Glc b1-
Glc b1-3 (Man a1-4) Gal b1-
Gal b1-4 Glc b1-3 Man a1-
Gal b1-6 Man a1-2 Glc a1-
Gal a1-2 Man b1-2 Glc b1-
Man a1-3 Glc b1-6 Gal a1-
Man a1-4 Gal a1-4 Glc a1-
Man a1-6 Gal b1-3 Glc b1
Glc b1-2 Man a1-2 Gal b1-
Glc b1-3 Gal a1-6 Man a1-
Glc b1-4 Gal b1-4 Man b1-
Gal a1-4 (Glc b1-3) Man b1-
Gal a1-2 (Man b1-3) Glc b1-
Glc b1-3 (Man a1-6) Gal b1-
Gal b1-6 Glc b1-3 Man a1-
Gal a1-2 Man a1-3 Glc a1-
Gal a1-3 Man b1-2 Glc b1-
Man a1-4 Glc b1-6 Gal a1-
Man a1-6 Gal a1-4 Glc a1-
Man b1-2 Gal b1-3 Glc b1
Glc b1-3 Man a1-2 Gal b1-
Glc b1-4 Gal a1-6 Man a1-
Glc b1-6 Gal b1-4 Man b1-
Gal a1-4 (Glc b1-6) Man b1-
Gal a1-2 (Man b1-4) Glc b1-
Glc b1-4 (Man a1-2) Gal b1-
Gal a1-2 Glc b1-4 Man a1-
Gal a1-3 Man a1-3 Glc a1-
Gal a1-4 Man b1-2 Glc b1-
Man a1-6 Glc b1-6 Gal a1-
Man b1-2 Gal a1-4 Glc a1-
Man b1-3 Gal b1-3 Glc b1
Glc b1-4 Man a1-2 Gal b1-
Glc b1-6 Gal a1-6 Man a1-
Glc a1-2 Gal b1-6 Man b1-
Gal a1-6 (Glc b1-2) Man b1-
Gal a1-2 (Man b1-6) Glc b1-
Glc b1-4 (Man a1-3) Gal b1-
Gal a1-3 Glc b1-4 Man a1-
Gal a1-4 Man a1-3 Glc a1-
Gal a1-6 Man b1-2 Glc b1-
Man b1-2 Glc b1-6 Gal a1-
Man b1-3 Gal a1-4 Glc a1-
Man b1-4 Gal b1-3 Glc b1
Glc b1-6 Man a1-2 Gal b1-
Glc a1-2 Gal b1-2 Man a1-
Glc a1-3 Gal b1-6 Man b1-
Gal a1-6 (Glc b1-3) Man b1-
Gal a1-3 (Man b1-2) Glc b1-
Glc b1-4 (Man a1-6) Gal b1-
Gal a1-4 Glc b1-4 Man a1-
Gal a1-6 Man a1-3 Glc a1-
Gal b1-2 Man b1-2 Glc b1-
Man b1-3 Glc b1-6 Gal a1-
Man b1-4 Gal a1-4 Glc a1-
Man b1-6 Gal b1-3 Glc b1
Glc a1-2 Man a1-3 Gal b1-
Glc a1-3 Gal b1-2 Man a1-
Glc a1-4 Gal b1-6 Man b1-
Gal a1-6 (Glc b1-4) Man b1-
Gal a1-3 (Man b1-4) Glc b1-
Glc b1-6 (Man a1-2) Gal b1-
Gal a1-6 Glc b1-4 Man a1-
Gal b1-2 Man a1-3 Glc a1-
Gal b1-3 Man b1-2 Glc b1-
Man b1-4 Glc b1-6 Gal a1-
Man b1-6 Gal a1-4 Glc a1-
Man a1-2 Gal b1-4 Glc b1
Glc a1-3 Man a1-3 Gal b1-
Glc a1-4 Gal b1-2 Man a1-
Glc a1-6 Gal b1-6 Man b1-
Gal b1-2 (Glc b1-3) Man b1-
Gal a1-3 (Man b1-6) Glc b1-
Glc b1-6 (Man a1-3) Gal b1-
Gal b1-2 Glc b1-4 Man a1-
Gal b1-3 Man a1-3 Glc a1-
Gal b1-4 Man b1-2 Glc b1-
Man b1-6 Glc b1-6 Gal a1-
Man a1-2 Gal a1-6 Glc a1-
Man a1-3 Gal b1-4 Glc b1
Glc a1-4 Man a1-3 Gal b1-
Glc a1-6 Gal b1-2 Man a1-
Glc b1-2 Gal b1-6 Man b1-
Gal b1-2 (Glc b1-4) Man b1-
Gal a1-4 (Man b1-2) Glc b1-
Glc b1-6 (Man a1-4) Gal b1-
Gal b1-3 Glc b1-4 Man a1-
Gal b1-4 Man a1-3 Glc a1-
Gal b1-6 Man b1-2 Glc b1-
Man a1-2 Glc a1-2 Gal b1-
Man a1-3 Gal a1-6 Glc a1-
Man a1-4 Gal b1-4 Glc b1
Glc a1-6 Man a1-3 Gal b1-
Glc b1-2 Gal b1-2 Man a1-
Glc b1-3 Gal b1-6 Man b1-
Gal b1-2 (Glc b1-6) Man b1-
Gal a1-4 (Man b1-3) Glc b1-
Glc a1-2 (Man b1-3) Gal b1-
Gal b1-4 Glc b1-4 Man a1-
Gal b1-6 Man a1-3 Glc a1-
Gal a1-2 Man b1-3 Glc b1-
Man a1-3 Glc a1-2 Gal b1-
Man a1-4 Gal a1-6 Glc a1-
Man a1-6 Gal b1-4 Glc b1
Glc b1-2 Man a1-3 Gal b1-
Glc b1-3 Gal b1-2 Man a1-
Glc b1-4 Gal b1-6 Man b1-
Gal b1-3 (Glc b1-2) Man b1-
Gal a1-4 (Man b1-6) Glc b1-
Glc a1-2 (Man b1-4) Gal b1-
Gal b1-6 Glc b1-4 Man a1-
Gal a1-2 Man a1-4 Glc a1-
Gal a1-3 Man b1-3 Glc b1-
Man a1-4 Glc a1-2 Gal b1-
Man a1-6 Gal a1-6 Glc a1-
Man b1-2 Gal b1-4 Glc b1
Glc b1-3 Man a1-3 Gal b1-
Glc b1-4 Gal b1-2 Man a1-
Glc b1-6 Gal b1-6 Man b1-
Gal b1-3 (Glc b1-4) Man b1-
Gal a1-6 (Man b1-2) Glc b1-
Glc a1-2 (Man b1-6) Gal b1-
Gal a1-2 Glc b1-6 Man a1-
Gal a1-3 Man a1-4 Glc a1-
Gal a1-4 Man b1-3 Glc b1-
Man a1-6 Glc a1-2 Gal b1-
Man b1-2 Gal a1-6 Glc a1-
Man b1-3 Gal b1-4 Glc b1
Glc b1-4 Man a1-3 Gal b1-
Glc b1-6 Gal b1-2 Man a1-
Gal a1-2 (Glc a1-3) Man a1-
Gal b1-3 (Glc b1-6) Man b1-
Gal a1-6 (Man b1-3) Glc b1-
Glc a1-3 (Man b1-2) Gal b1-
Gal a1-3 Glc b1-6 Man a1-
Gal a1-4 Man a1-4 Glc a1-
Gal a1-6 Man b1-3 Glc b1-
Man b1-2 Glc a1-2 Gal b1-
Man b1-3 Gal a1-6 Glc a1-
Man b1-4 Gal b1-4 Glc b1
Glc b1-6 Man a1-3 Gal b1-
Glc a1-2 Gal b1-3 Man a1-
Gal a1-2 (Glc a1-4) Man a1-
Gal b1-4 (Glc b1-2) Man b1-
Gal a1-6 (Man b1-4) Glc b1-
Glc a1-3 (Man b1-4) Gal b1-
Gal a1-4 Glc b1-6 Man a1-
Gal a1-6 Man a1-4 Glc a1-
Gal b1-2 Man b1-3 Glc b1-
Man b1-3 Glc a1-2 Gal b1-
Man b1-4 Gal a1-6 Glc a1-
Man b1-6 Gal b1-4 Glc b1
Glc a1-2 Man a1-4 Gal b1-
Glc a1-3 Gal b1-3 Man a1-
Gal a1-2 (Glc a1-6) Man a1-
Gal b1-4 (Glc b1-3) Man b1-
Gal b1-2 (Man b1-3) Glc b1-
Glc a1-3 (Man b1-6) Gal b1-
Gal a1-6 Glc b1-6 Man a1-
Gal b1-2 Man a1-4 Glc a1-
Gal b1-3 Man b1-3 Glc b1-
Man b1-4 Glc a1-2 Gal b1-
Man b1-6 Gal a1-6 Glc a1-
Man a1-2 Gal b1-6 Glc b1
Glc a1-3 Man a1-4 Gal b1-
Glc a1-4 Gal b1-3 Man a1-
Gal a1-3 (Glc a1-2) Man a1-
Gal b1-4 (Glc b1-6) Man b1-
Gal b1-2 (Man b1-4) Glc b1-
Glc a1-4 (Man b1-2) Gal b1-
Gal b1-2 Glc b1-6 Man a1-
Gal b1-3 Man a1-4 Glc a1-
Gal b1-4 Man b1-3 Glc b1-
Man b1-6 Glc a1-2 Gal b1-
Man a1-2 Gal b1-2 Glc a1-
Man a1-3 Gal b1-6 Glc b1
Glc a1-4 Man a1-4 Gal b1-
Glc a1-6 Gal b1-3 Man a1-
Gal a1-3 (Glc a1-4) Man a1-
Gal b1-6 (Glc b1-2) Man b1-
Gal b1-2 (Man b1-6) Glc b1-
Glc a1-4 (Man b1-3) Gal b1-
Gal b1-3 Glc b1-6 Man a1-
Gal b1-4 Man a1-4 Glc a1-
Gal b1-6 Man b1-3 Glc b1-
Man a1-2 Glc a1-3 Gal b1-
Man a1-3 Gal b1-2 Glc a1-
Man a1-4 Gal b1-6 Glc b1
Glc a1-6 Man a1-4 Gal b1-
Glc b1-2 Gal b1-3 Man a1-
Gal a1-3 (Glc a1-6) Man a1-
Gal b1-6 (Glc b1-3) Man b1-
Gal b1-3 (Man b1-2) Glc b1-
Glc a1-4 (Man b1-6) Gal b1-
Gal b1-4 Glc b1-6 Man a1-
Gal b1-6 Man a1-4 Glc a1-
Gal a1-2 Man b1-4 Glc b1-
Man a1-3 Glc a1-3 Gal b1-
Man a1-4 Gal b1-2 Glc a1-
Man a1-6 Gal b1-6 Glc b1
Glc b1-2 Man a1-4 Gal b1-
Glc b1-3 Gal b1-3 Man a1-
Gal a1-4 (Glc a1-2) Man a1-
Gal b1-6 (Glc b1-4) Man b1-
Gal b1-3 (Man b1-4) Glc b1-
Glc a1-6 (Man b1-2) Gal b1-
Gal b1-6 Glc b1-6 Man a1-
Gal a1-2 Man a1-6 Glc a1-
Gal a1-3 Man b1-4 Glc b1-
Man a1-4 Glc a1-3 Gal b1-
Man a1-6 Gal b1-2 Glc a1-
Man b1-2 Gal b1-6 Glc b1
Glc b1-3 Man a1-4 Gal b1-
Glc b1-4 Gal b1-3 Man a1-
Gal a1-4 (Glc a1-3) Man a1-
Gal a1-2 (Man a1-3) Glc a1-
Gal b1-3 (Man b1-6) Glc b1-
Glc a1-6 (Man b1-3) Gal b1-
Gal a1-2 Glc a1-2 Man b1-
Gal a1-3 Man a1-6 Glc a1-
Gal a1-4 Man b1-4 Glc b1-
Man a1-6 Glc a1-3 Gal b1-
Man b1-2 Gal b1-2 Glc a1-
Man b1-3 Gal b1-6 Glc b1
Glc b1-4 Man a1-4 Gal b1-
Glc b1-6 Gal b1-3 Man a1-
Gal a1-4 (Glc a1-6) Man a1-
Gal a1-2 (Man a1-4) Glc a1-
Gal b1-4 (Man b1-2) Glc b1-
Glc a1-6 (Man b1-4) Gal b1-
Gal a1-3 Glc a1-2 Man b1-
Gal a1-4 Man a1-6 Glc a1-
Gal a1-6 Man b1-4 Glc b1-
Man b1-2 Glc a1-3 Gal b1-
Man b1-3 Gal b1-2 Glc a1-
Man b1-4 Gal b1-6 Glc b1
Glc b1-6 Man a1-4 Gal b1-
Glc a1-2 Gal b1-4 Man a1-
Gal a1-6 (Glc a1-2) Man a1-
Gal a1-2 (Man a1-6) Glc a1-
Gal b1-4 (Man b1-3) Glc b1-
Glc b1-2 (Man b1-3) Gal b1-
Gal a1-4 Glc a1-2 Man b1-
Gal a1-6 Man a1-6 Glc a1-
Gal b1-2 Man b1-4 Glc b1-
Man b1-3 Glc a1-3 Gal b1-
Man b1-4 Gal b1-2 Glc a1-
Man b1-6 Gal b1-6 Glc b1
Glc a1-2 Man a1-6 Gal b1-
Glc a1-3 Gal b1-4 Man a1-
Gal a1-6 (Glc a1-3) Man a1-
Gal a1-3 (Man a1-2) Glc a1-
Gal b1-4 (Man b1-6) Glc b1-
Glc b1-2 (Man b1-4) Gal b1-
Gal a1-6 Glc a1-2 Man b1-
Gal b1-2 Man a1-6 Glc a1-
Gal b1-3 Man b1-4 Glc b1-
Man b1-4 Glc a1-3 Gal b1-
Man b1-6 Gal b1-2 Glc a1-
Glc a1-2 Man a1-2 Gal a1-
Glc a1-3 Man a1-6 Gal b1-
Glc a1-4 Gal b1-4 Man a1-
Gal a1-6 (Glc a1-4) Man a1-
Gal a1-3 (Man a1-4) Glc a1-
Gal b1-6 (Man b1-2) Glc b1-
Glc b1-2 (Man b1-6) Gal b1-
Gal b1-2 Glc a1-2 Man b1-
Gal b1-3 Man a1-6 Glc a1-
Gal b1-4 Man b1-4 Glc b1-
Man b1-6 Glc a1-3 Gal b1-
Man a1-2 Gal b1-3 Glc a1-
Glc a1-3 Man a1-2 Gal a1-
Glc a1-4 Man a1-6 Gal b1-
Glc a1-6 Gal b1-4 Man a1-
Gal b1-2 (Glc a1-3) Man a1-
Gal a1-3 (Man a1-6) Glc a1-
Gal b1-6 (Man b1-3) Glc b1-
Glc b1-3 (Man b1-2) Gal b1-
Gal b1-3 Glc a1-2 Man b1-
Gal b1-4 Man a1-6 Glc a1-
Gal b1-6 Man b1-4 Glc b1-
Man a1-2 Glc a1-4 Gal b1-
Man a1-3 Gal b1-3 Glc a1-
Glc a1-4 Man a1-2 Gal a1-
Glc a1-6 Man a1-6 Gal b1-
Glc b1-2 Gal b1-4 Man a1-
Gal b1-2 (Glc a1-4) Man a1-
Gal a1-4 (Man a1-2) Glc a1-
Gal b1-6 (Man b1-4) Glc b1-
Glc b1-3 (Man b1-4) Gal b1-
Gal b1-4 Glc a1-2 Man b1-
Gal b1-6 Man a1-6 Glc a1-
Gal a1-2 Man b1-6 Glc b1-
Man a1-3 Glc a1-4 Gal b1-
Man a1-4 Gal b1-3 Glc a1-
Glc a1-6 Man a1-2 Gal a1-
Glc b1-2 Man a1-6 Gal b1-
Glc b1-3 Gal b1-4 Man a1-
Gal b1-2 (Glc a1-6) Man a1-
Gal a1-4 (Man a1-3) Glc a1-
Glc a1-2 (Man a1-3) Gal a1-
Glc b1-3 (Man b1-6) Gal b1-
Gal b1-6 Glc a1-2 Man b1-
Gal a1-2 Man b1-2 Glc a1-
Gal a1-3 Man b1-6 Glc b1-
Man a1-4 Glc a1-4 Gal b1-
Man a1-6 Gal b1-3 Glc a1-
Glc b1-2 Man a1-2 Gal a1-
Glc b1-3 Man a1-6 Gal b1-
Glc b1-4 Gal b1-4 Man a1-
Gal b1-3 (Glc a1-2) Man a1-
Gal a1-4 (Man a1-6) Glc a1-
Glc a1-2 (Man a1-4) Gal a1-
Glc b1-4 (Man b1-2) Gal b1-
Gal a1-2 Glc a1-3 Man b1-
Gal a1-3 Man b1-2 Glc a1-
Gal a1-4 Man b1-6 Glc b1-
Man a1-6 Glc a1-4 Gal b1-
Man b1-2 Gal b1-3 Glc a1-
Glc b1-3 Man a1-2 Gal a1-
Glc b1-4 Man a1-6 Gal b1-
Glc b1-6 Gal b1-4 Man a1-
Gal b1-3 (Glc a1-4) Man a1-
Gal a1-6 (Man a1-2) Glc a1-
Glc a1-2 (Man a1-6) Gal a1-
Glc b1-4 (Man b1-3) Gal b1-
Gal a1-3 Glc a1-3 Man b1-
Gal a1-4 Man b1-2 Glc a1-
Gal a1-6 Man b1-6 Glc b1-
Man b1-2 Glc a1-4 Gal b1-
Man b1-3 Gal b1-3 Glc a1-
Glc b1-4 Man a1-2 Gal a1-
Glc b1-6 Man a1-6 Gal b1-
Glc a1-2 Gal b1-6 Man a1-
Gal b1-3 (Glc a1-6) Man a1-
Gal a1-6 (Man a1-3) Glc a1-
Glc a1-3 (Man a1-2) Gal a1-
Glc b1-4 (Man b1-6) Gal b1-
Gal a1-4 Glc a1-3 Man b1-
Gal a1-6 Man b1-2 Glc a1-
Gal b1-2 Man b1-6 Glc b1-
Man b1-3 Glc a1-4 Gal b1-
Man b1-4 Gal b1-3 Glc a1-
Glc b1-6 Man a1-2 Gal a1-
Glc a1-2 Man b1-2 Gal b1-
Glc a1-3 Gal b1-6 Man a1-
Gal b1-4 (Glc a1-2) Man a1-
Gal a1-6 (Man a1-4) Glc a1-
Glc a1-3 (Man a1-4) Gal a1-
Glc b1-6 (Man b1-2) Gal b1-
Gal a1-6 Glc a1-3 Man b1-
Gal b1-2 Man b1-2 Glc a1-
Gal b1-3 Man b1-6 Glc b1-
Man b1-4 Glc a1-4 Gal b1-
Man b1-6 Gal b1-3 Glc a1-
Glc a1-2 Man a1-3 Gal a1-
Glc a1-3 Man b1-2 Gal b1-
Glc a1-4 Gal b1-6 Man a1-
Gal b1-4 (Glc a1-3) Man a1-
Gal b1-2 (Man a1-3) Glc a1-
Glc a1-3 (Man a1-6) Gal a1-
Glc b1-6 (Man b1-3) Gal b1-
Gal b1-2 Glc a1-3 Man b1-
Gal b1-3 Man b1-2 Glc a1-
Gal b1-4 Man b1-6 Glc b1-
Man b1-6 Glc a1-4 Gal b1-
Man a1-2 Gal b1-4 Glc a1-
Glc a1-3 Man a1-3 Gal a1-
Glc a1-4 Man b1-2 Gal b1-
Glc a1-6 Gal b1-6 Man a1-
Gal b1-4 (Glc a1-6) Man a1-
Gal b1-2 (Man a1-4) Glc a1-
Glc a1-4 (Man a1-2) Gal a1-
Glc b1-6 (Man b1-4) Gal b1-
Gal b1-3 Glc a1-3 Man b1-
Gal b1-4 Man b1-2 Glc a1-
Gal b1-6 Man b1-6 Glc b1-
Man a1-2 Glc a1-6 Gal b1-
Man a1-3 Gal b1-4 Glc a1-
Glc a1-4 Man a1-3 Gal a1-
Glc a1-6 Man b1-2 Gal b1-
Glc b1-2 Gal b1-6 Man a1-
Gal b1-6 (Glc a1-2) Man a1-
Gal b1-2 (Man a1-6) Glc a1-
Glc a1-4 (Man a1-3) Gal a1-
Gal b1-4 Glc a1-3 Man b1-
Gal b1-6 Man b1-2 Glc a1-
Man a1-2 Glc a1-2 Gal a1-
Man a1-3 Glc a1-6 Gal b1-
Man a1-4 Gal b1-4 Glc a1-
Glc a1-6 Man a1-3 Gal a1-
Glc b1-2 Man b1-2 Gal b1-
Glc b1-3 Gal b1-6 Man a1-
Gal b1-6 (Glc a1-3) Man a1-
Gal b1-3 (Man a1-2) Glc a1-
Glc a1-4 (Man a1-6) Gal a1-
Gal b1-6 Glc a1-3 Man b1-
Gal a1-2 Man b1-3 Glc a1-
Man a1-3 Glc a1-2 Gal a1-
Man a1-4 Glc a1-6 Gal b1-
Man a1-6 Gal b1-4 Glc a1-
Glc b1-2 Man a1-3 Gal a1-
Glc b1-3 Man b1-2 Gal b1-
Glc b1-4 Gal b1-6 Man a1-
Gal b1-6 (Glc a1-4) Man a1-
Gal b1-3 (Man a1-4) Glc a1-
Glc a1-6 (Man a1-2) Gal a1-
Gal a1-2 Glc a1-4 Man b1-
Gal a1-3 Man b1-3 Glc a1-
Man a1-4 Glc a1-2 Gal a1-
Man a1-6 Glc a1-6 Gal b1-
Man b1-2 Gal b1-4 Glc a1-
Glc b1-3 Man a1-3 Gal a1-
Glc b1-4 Man b1-2 Gal b1-
Glc b1-6 Gal b1-6 Man a1-
Gal a1-2 (Glc b1-3) Man a1-
Gal b1-3 (Man a1-6) Glc a1-
Glc a1-6 (Man a1-3) Gal a1-
Gal a1-3 Glc a1-4 Man b1-
Gal a1-4 Man b1-3 Glc a1-
Man a1-6 Glc a1-2 Gal a1-
Man b1-2 Glc a1-6 Gal b1-
Man b1-3 Gal b1-4 Glc a1-
Glc b1-4 Man a1-3 Gal a1-
Glc b1-6 Man b1-2 Gal b1-
Glc a1-2 Gal a1-2 Man b1-
Gal a1-2 (Glc b1-4) Man a1-
Gal b1-4 (Man a1-2) Glc a1-
Glc a1-6 (Man a1-4) Gal a1-
Gal a1-4 Glc a1-4 Man b1-
Gal a1-6 Man b1-3 Glc a1-
Man b1-2 Glc a1-2 Gal a1-
Man b1-3 Glc a1-6 Gal b1-
Man b1-4 Gal b1-4 Glc a1-
Glc b1-6 Man a1-3 Gal a1-
Glc a1-2 Man b1-3 Gal b1-
Glc a1-3 Gal a1-2 Man b1-
Gal a1-2 (Glc b1-6) Man a1-
Gal b1-4 (Man a1-3) Glc a1-
Glc b1-2 (Man a1-3) Gal a1-
Gal a1-6 Glc a1-4 Man b1-
Gal b1-2 Man b1-3 Glc a1-
Man b1-3 Glc a1-2 Gal a1-
Man b1-4 Glc a1-6 Gal b1-
Man b1-6 Gal b1-4 Glc a1-
Glc a1-2 Man a1-4 Gal a1-
Glc a1-3 Man b1-3 Gal b1-
Glc a1-4 Gal a1-2 Man b1-
Gal a1-3 (Glc b1-2) Man a1-
Gal b1-4 (Man a1-6) Glc a1-
Glc b1-2 (Man a1-4) Gal a1-
Gal b1-2 Glc a1-4 Man b1-
Gal b1-3 Man b1-3 Glc a1-
Man b1-4 Glc a1-2 Gal a1-
Man b1-6 Glc a1-6 Gal b1-
Man a1-2 Gal b1-6 Glc a1-
Glc a1-3 Man a1-4 Gal a1-
Glc a1-4 Man b1-3 Gal b1-
Glc a1-6 Gal a1-2 Man b1-
Gal a1-3 (Glc b1-4) Man a1-
Gal b1-6 (Man a1-2) Glc a1-
Glc b1-2 (Man a1-6) Gal a1-
Gal b1-3 Glc a1-4 Man b1-
Gal b1-4 Man b1-3 Glc a1-
Man b1-6 Glc a1-2 Gal a1-
Man a1-2 Glc b1-2 Gal b1-
Man a1-3 Gal b1-6 Glc a1-
Glc a1-4 Man a1-4 Gal a1-
Glc a1-6 Man b1-3 Gal b1-
Glc b1-2 Gal a1-2 Man b1-
Gal a1-3 (Glc b1-6) Man a1-
Gal b1-6 (Man a1-3) Glc a1-
Glc b1-3 (Man a1-2) Gal a1-
Gal b1-4 Glc a1-4 Man b1-
Gal b1-6 Man b1-3 Glc a1-
Man a1-2 Glc a1-3 Gal a1-
Man a1-3 Glc b1-2 Gal b1-
Man a1-4 Gal b1-6 Glc a1-
Glc a1-6 Man a1-4 Gal a1-
Glc b1-2 Man b1-3 Gal b1-
Glc b1-3 Gal a1-2 Man b1-
Gal a1-4 (Glc b1-2) Man a1-
Gal b1-6 (Man a1-4) Glc a1-
Glc b1-3 (Man a1-4) Gal a1-
Gal b1-6 Glc a1-4 Man b1-
Gal a1-2 Man b1-4 Glc a1-
Man a1-3 Glc a1-3 Gal a1-
Man a1-4 Glc b1-2 Gal b1-
Man a1-6 Gal b1-6 Glc a1-
Glc b1-2 Man a1-4 Gal a1-
Glc b1-3 Man b1-3 Gal b1-
Glc b1-4 Gal a1-2 Man b1-
Gal a1-4 (Glc b1-3) Man a1-
Gal a1-2 (Man b1-3) Glc a1-
Glc b1-3 (Man a1-6) Gal a1-
Gal a1-2 Glc a1-6 Man b1-
Gal a1-3 Man b1-4 Glc a1-
Man a1-4 Glc a1-3 Gal a1-
Man a1-6 Glc b1-2 Gal b1-
Man b1-2 Gal b1-6 Glc a1-
Glc b1-3 Man a1-4 Gal a1-
Glc b1-4 Man b1-3 Gal b1-
Glc b1-6 Gal a1-2 Man b1-
Gal a1-4 (Glc b1-6) Man a1-
Gal a1-2 (Man b1-4) Glc a1-
Glc b1-4 (Man a1-2) Gal a1-
Man a1-4 Gal a1-3 Glc b1
Man a1-6 Gal a1-3 Glc b1
Man b1-2 Gal a1-3 Glc b1
Man b1-3 Gal a1-3 Glc b1
Man b1-4 Gal a1-3 Glc b1
Man b1-6 Gal a1-3 Glc b1
Man a1-2 Gal a1-4 Glc b1
Man a1-3 Gal a1-4 Glc b1
Man a1-4 Gal a1-4 Glc b1
Man a1-6 Gal a1-4 Glc b1
Man b1-2 Gal a1-4 Glc b1
Man b1-3 Gal a1-4 Glc b1
Man b1-4 Gal a1-4 Glc b1
Man b1-6 Gal a1-4 Glc b1
Man a1-2 Gal a1-6 Glc b1
Man a1-3 Gal a1-6 Glc b1
Cummings RD (2009) Molecular BioSystems 5, 1087
*Glycoproteins and glycolipids may contain ~3000 glycan determinants with an additional ~4000 theoretical petasaccharide sequeces in glycosaminoglycans

44. Saccharides Carbohydrates: The language of glycobiology
The glycosidic bond and glycan nomenclature
Major vertebrate glycan classes

45. Saccharides Carbohydrates: The language of glycobiology
The glycosidic bond and glycan nomenclature
Major vertebrate glycan classes

46. Major Glycans of Eukaryotes
Glycoproteins
Glycolipids
Proteoglycans

47. Major Glycans of Eukaryotes
Glycoproteins
Glycolipids
Proteoglycans

48. Glycoproteins N-Linked O-Linked GPI Anchor O-GlcNAc
*A non-inclusive list!

49. Glycoproteins N-Linked O-Linked GPI Anchor O-GlcNAc
*A non-inclusive list!

50. “N-linked” glycan linkage to protein asparagine residues

51. Families of N-linked glycan structures

52. Terminal Saccharide Diversity --- A key to recognition
Examples of structures found as termini on the branches of complex N-linked glycoprotein glycans….
NeuAc 2-6 Gal 1-4 GlcNAc---
NeuAc 2-3 Gal 1-4 GlcNAc---
Gal 1-3 Gal 1-4 GlcNAc---
4-SO3-GalNAc 1-4 GlcNAc---
(-Gal 1-4 GlcNAc 1-3-)n = polylactosamine repeats (n may be >6)
(-NeuAc 2-8-) n = polysialic acid (n may be >50)
Fuc residues (e.g. Fuc 1-2 Gal; Fuc 1-3 GlcNAc; Fuc 1-4 GlcNAc

53. Glycoproteins N-Linked O-Linked GPI Anchor O-GlcNAc
*A non-inclusive list!

54. Glycoproteins N-Linked O-Linked GPI Anchor O-GlcNAc
*A non-inclusive list!

55. “O-linked” glycan linkage to protein serine residues

56. Examples of variations of O-linked glycans

57. Glycoproteins N-Linked O-Linked GPI Anchor O-GlcNAc
*A non-inclusive list!

58. Glycoproteins N-Linked O-Linked GPI Anchor O-GlcNAc
*A non-inclusive list!

59. GPI (glycosylphosphatidylinositol) anchored protein

60. CD59, a complement defense glycoprotein
3 kDa N-linked glycan
20 kDa protein
1 kDa O-linked glycan
1.5 kDa GPI anchor
plasma membrane

61. Glycoproteins N-Linked O-Linked GPI Anchor O-GlcNAc
*A non-inclusive list!

62. Glycoproteins N-Linked O-Linked GPI Anchor O-GlcNAc
*A non-inclusive list!

63. O-GlcNAc Note: No further sugar substitutions have been confirmed
Highly dynamic post-translational modification!

64. Major Glycans of Eukaryotes
Glycoproteins
Glycolipids
Proteoglycans

65. Major Glycans of Eukaryotes
Glycoproteins
Glycolipids
Proteoglycans

66. Galactosylceramide (GalCer)
A Glycosphingolipid
Galactosylceramide (GalCer)

67. A Ganglioside
“GD1a”

68. Major Glycans of Eukaryotes
Glycoproteins
Glycolipids
Proteoglycans

69. Major Glycans of Eukaryotes
Glycoproteins
Glycolipids
Proteoglycans

70. Glycosaminoglycans (GAG’s) and Proteoglycans
long linear glycans made of repeating disaccharides
Hyaluronic acid is the only “stand-alone” GAG, other GAG’s are constituents of …
PROTEOGLYCANS
GAG’s on proteins
Defined by their repeating disaccharide units
GAG’s on proteoglycans are sulfated

71. Hyaluronic acid -- a “simple” space filling molecule
(GlcU β4 GlcNAc)n

72. Post-polymerization variations in glycosaminoglycans

73. Cartilage proteoglycan

74. Cartilage proteoglycan

75. Glycan Biosynthesis
Glycosyltransferase reaction (UDP-Gal:glucose β4 galactosyltransferase)
UDP-Glc
UDP-Gal
GDP-Man
UDP-GlcNAc
UDP-GalNAc
UDP-GlcA
UDP-Xyl
GDP-Fuc
CMP-NeuAc
Activated Sugars:

76. Glycoprotein biosynthesis
N-Linked – en-bloc preconstructed core, trimming, terminal elaboration
O-Linked – stepwise sugar by sugar addition
O-GlcNAc - dynamic transferase/glycosidase
GPI Anchor – en-bloc preconstructed core, elaboration
Glycolipid biosynthesis
Stepwise sugar-by-sugar addition
Proteoglycan biosynthesis
Stepwise sugar-by-sugar addition (core and repeating disaccharide)
Post-polymerization modifications

77. Introduction to glycobiology
“What the matter, Sal, not up on your glycobiology?
H Ford (2010) Extraordinary Measures, CBS Films, Los Angeles, CA, USA

78. Harrison Ford and Brendon Fraser (2010) Extraordinary Measures

79. Lysosomal storage diseases are often due to faulty glycan catabolism
Hurler
(alpha-L iduronidase)
Hunter
(iduronate-2-sulfatase)
I-cell
(GlcNAc phosphotransferase)

80. Lysosomal storage diseases can be studied using patient cells in culture
I-cell lyphocytes
van der Meer et al (2001) J Clin Pathol 54:724
I-cell fibroblasts
Hanai et al (1971) Am J Dis Child 122:34

81. Fibroblasts from Hunter & Hurler patients build up glycosaminoglycans
Co-incubation with normal fibroblasts or each other corrects the buildup…
Correction is via a soluble factor
(direct contact not required).
Fratantoni et al (1968) Science 162:170

82. Corrective factor properties
Purified lysosomal hydrolases are taken up by fibroblasts – different enzymes correct storage of different diseases
Periodate pre-treatment of lysosomal hydrolases (cleaves sugar C-C bonds) inhibited enzyme uptake
Enzyme uptake was selectively blocked by mannose
Enzyme uptake was blocked better mannose-6-phosphate
Phosphatase pre-treatment of the enzyme blocked its uptake
Fibroblasts do not take up I-cell lysosomal hydrolases
Normal lysosomal hydrolases have mannose-6-phosphate residues (unusual!) on their N-linked glycans
I-cell patients are deficient in addition of 6-linked phosphate to mannose on their N-linked glycans

83. Lysosomal enzyme targeting
Dahms et al (1989) J Biol Chem 264:12115

84. Discovery: A unique and specific modification of lysosomal hydrolases for their trafficking to lysosomes
Bohnsack et al (2009) J Biol Chem 284:35215

85. Sugar-modifying enzyme lacking in I-cell disease:
N-acetylglucosamine-1-phosphate transferase
Reproducing this same Man-6-P modification on expressed therapeutic lysosomal hydrolases effectively targets them to the lysosome in vivo

86. William Canfield and John Crowley, Novazyme (http://blog.newok.com)
H Ford and B Fraser (2010) Extraordinary Measures, CBS Films, Los Angeles, CA, USA

87. Introduction to glycobiology
Date
Day
Lecture
Faculty
Mar 27
Mon
Saccharides & The Glyco World
Dr. R. Schnaar
Mar 28
Tue
Glycoproteins 1
Dr. N. Zachara
Mar 29
Wed
Glycoproteins 2
Mar 30
Thu
O-GlcNAc
Dr. G. Hart
Mar 31
Fri
Glycolipids and GPI anchors
Apr 3
Hyaluronan and Proteoglycans
Apr 4
Carbohydrate Engineering
Dr. K. Yarema
Apr 5
Protein-Glycan Recognition
Apr 5*
Glycan Binding Protein Functions
Apr 6
Glycomics (Analytical Glycobiology)
Apr 6*
Glycans and Disease