saccharides, glycosides & glycans

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Presentation transcript:

saccharides, glycosides & glycans The Glyco World saccharides, glycosides & glycans What’s the (sugar) buzz? Carbohydrates: The language of glycoscience The glycosidic bond and glycan nomenclature Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates Definitions and resources

saccharides, glycosides & glycans The Glyco World saccharides, glycosides & glycans What’s the (sugar) buzz? Carbohydrates: The language of glycoscience The glycosidic bond and glycan nomenclature Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates Definitions and resources

National Academies Press (2012) “Understanding the structures and functions of glycans is central to understanding biology.” “… Glycoscience researchers have developed a knowledge base that can be used to address many of today’s major research problems. When combined with current tools, it is a powerful resource to better understand human, plant, and microbial biology..”

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

Unique to yeast – NO! 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

The Eukaryotic Cell Surface ? Tiny sugar “decorations”.. added as an afterthought Lodish, et al. (1995) Molecular Cell Biology 3rd ed.

Eukaryotic cell surface The “glycocalyx” surrounding a fibroblast – glycans stained black extracellular lipid bilayer fibroblast intracellular Martinez-Palomo, A., et al. Cancer Res. 29, 925-937, 1969 “Every eukaryotic cell is covered with a dense and complex array of glycans, which also feature prominently in extracellular matrix and secreted soluble molecules.” … in fact… “Evolution has failed to generate a [single] living cell devoid of surface glycosylation” - A. Varki

Tropical Forest Canopy Ajit Varki, “Perspectives on the Future of Glycobiology,” Athens, GA, 14-Mar-2011

Tropical Forest Canopy Cohen & Varki (2010) OMICS 4:455 Ajit Varki, “Perspectives on the Future of Glycobiology,” Athens, GA, 14-Mar-2011

The Cell Surface Textbook image Real image fibroblast Martinez-Palomo, A., et al. Cancer Res. 29, 925-937, 1969

Glycobiology = Language (semiotics) Cohen & Varki (2010) OMICS 4:455 Rosetta Stone, British Museum

saccharides, glycosides & glycans The Glyco World saccharides, glycosides & glycans What’s the (sugar) buzz? Carbohydrates: The language of glycoscience The glycosidic bond and glycan nomenclature Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates Definitions and resources

saccharides, glycosides & glycans The Glyco World saccharides, glycosides & glycans What’s the (sugar) buzz? Carbohydrates: The language of glycoscience The glycosidic bond and glycan nomenclature Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates Definitions and resources

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

glucose fructose Generalized Ketose Generalized Aldose

Generalized Aldose Glycoaldehyde

mirror images of each other that are not superimposable. Generalized Aldose Enantiomers: mirror images of each other that are not superimposable. Diastereomers: stereoisomers that are not enantiomers.

Fischer projection D-glyceraldehyde

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

Diasteriomers * * * Highest numbered asymmetric carbon = reference carbon

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

Essentials of Glycobiology * * epimers: differ in only stereogenic center Essentials of Glycobiology Second Edition

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 Taylor & Drickamer (2011) Introduction to Glycobiology, 3rd edition

Determining anomeric configuration [PDB] Same direction as reference carbon = α Different direction from reference carbon = β Lee & Lee (1999) J Chinese Chem Soc 46:283-291

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

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

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

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

saccharides, glycosides & glycans The Glyco World saccharides, glycosides & glycans What’s the (sugar) buzz? Carbohydrates: The language of glycoscience The glycosidic bond and glycan nomenclature Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates Definitions and resources

saccharides, glycosides & glycans The Glyco World saccharides, glycosides & glycans What’s the (sugar) buzz? Carbohydrates: The language of glycoscience The glycosidic bond and glycan nomenclature Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates Definitions and resources

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

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

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

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

saccharides, glycosides & glycans The Glyco World saccharides, glycosides & glycans What’s the (sugar) buzz? Carbohydrates: The language of glycoscience The glycosidic bond and glycan nomenclature Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates Definitions and resources

saccharides, glycosides & glycans The Glyco World saccharides, glycosides & glycans What’s the (sugar) buzz? Carbohydrates: The language of glycoscience The glycosidic bond and glycan nomenclature Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates Definitions and resources

Sugars, polysaccharides, oligosaccharides and glycoconjugates Simple mono- or disaccharides: often from plants or breakdown products of plant polysaccharides. Examples: glucose, sucrose (glucose α1-2 fructose), maltose (Glc α1-4 Glc), lactose (Gal β1-4 Glc). Polysaccharides: long polymers (linear or branched) of a single monosaccharide Examples: Cellulose, amylose (starch), glycogen, chitin Oligosaccharides: groups of monosaccharides (e.g. 3 or more) in linear or branched glycosidic linkage Examples: Sugars groups bound to proteins or lipids to form glycoconjugates (see below) Glycoconjugates Examples: Glycoproteins, glycolipids, proteoglycans

Examples of polysaccharides: Cellulose Most abundant organic compound on Earth. ~90% of cotton fiber, 50% of wood, 33% of all plant matter. (β1-4 Glc β1-4 Glc)n Intra- and inter-strand hydrogen bonding provides strength Material sciences http://en.wikipedia.org/wiki/Cellulose

Examples of polysaccharides: Amylose Linear (amylose) and branched (amylopectin) forms are the carbohydrates of starch. This major food source is enzymatically broken down to glucose during digestion… (α1-4 Glc α1-4 Glc)n …and during ethanol production α1-6 Glc branches http://en.wikipedia.org/wiki/Amylopectin

Examples of polysaccharides: Glycogen Tissue storage form of glucose (primarily in the liver & muscle). “Animal Starch” – same general structure as plant starch, but more branched & compact. Broken down to glucose at need to quickly increase blood glucose levels. (α1-4 Glc α1-4 Glc)n α1-6 Glc branches http://en.wikipedia.org/wiki/Glycogen

Examples of polysaccharides: Chitin Among the most abundant of organic molecules on Earth, it is the main component of the cell walls of fungi, the exoskeletons of arthropods such as insects and crustaceans (e.g., crabs, lobsters and shrimps). (β1-4 GlcNAc β1-4 GlcNAc)n http://en.wikipedia.org/wiki/Chitin

Glycobiology = Language (semiotics) Cohen & Varki (2010) OMICS 4:455 Rosetta Stone, British Museum

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

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 …

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

Major Glycoconjugates of Eukaryotes Glycoproteins Glycolipids Proteoglycans

saccharides, glycosides & glycans The Glyco World saccharides, glycosides & glycans What’s the (sugar) buzz? Carbohydrates: The language of glycoscience The glycosidic bond and glycan nomenclature Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates Definitions and resources

saccharides, glycosides & glycans The Glyco World saccharides, glycosides & glycans What’s the (sugar) buzz? Carbohydrates: The language of glycoscience The glycosidic bond and glycan nomenclature Major carbohydrate classes: sugars, polysaccharides, oligosaccharides and glycoconjugates Definitions and resources

What are: Glycobiology? Glycosciences? Glycomics?

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).

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

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

Glycobiology resources Oxford University Press, New York Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY. Content freely available at: http://www.ncbi.nlm.nih.gov/books/NBK1908

http://glycam.ccrc.uga.edu/ccrc/pages/3dspt.html