1. FOOD CARBOHYDRATES Spring - 2013 John D. Keller, Jr. (MS)
Food Industry Consultant
Visiting Professor
Lecture #1 - Simple Sugars -
Classification/Structures/Nomenclature
Rutgers Office: By Appointment
Home Office: (732) (P/Fax);

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3. ADMINISTRATIVE I Lecture/Exam Schedule Exams/Quizes Lectures/Notes

4.
alginking

6. ADMINISTRATIVE II References CHO Chem for Food Sci’s
Food Chemistry – Fennema, 4th ed.
Adv Org Chem
Handbook of Hydrocolloids
Miscellaneous
Classes

7. CHO Chem for Fd Scientists, 2nd Ed
CHO Chem for Fd Scientists, 2nd Ed. (ca $169, from AACC) (see site below)

8. Aliphatic polyhydroxy cpds which usually carry a carbonyl group
Introduction I
Definition/Nomenclature
CHO Classification
CHO Metabolism
Carbohydrates in Foods
Aliphatic polyhydroxy cpds which usually carry a carbonyl group

9. Carbohydrate = Carbon Hydrate
i.e., C(H2O) or
Cn(H2O)n , or
C6(H2O)6 = C6H12O6
CO2 + H2O Sugar + O 2 ↑

10. Definition/Nomenclature
Introduction II
Definition/Nomenclature
Chiral Carbons A D E B C A D E B C
mirror

11. Simple Sugar Nomenclature I Prefixes and Suffixes
ALDO- = carbonyl at #1 carbon, i.e., an aldehyde
KETO- = carbonyl at #2 carbon, i.e., a ketone
-OSE = free sugar, esp. aldose sugar
-ULOSE = free keto sugar
-ITOL = CHO alcohol w/ two 1o -OH groups
-ONIC = -COOH (carboxyl) group at anomeric carbon
-URONIC = -COOH (carboxyl) group at 1o carbon
-ARIC = -COOH (carboxyl) groups at both ends of the sugar molecule (e.g., #1 & #6 carbons)
-OSIDE = substitution at anomeric carbon = glycoside
-AN = polymer. E.g., glucan = glucose polymer

12. Simple Sugar Nomenclature II
ISOMERS = compounds with same chemical composition but different structures. (very general term, e.g. family of isomers with C6H12O6 formula)
STEREOISOMERS = isomers differing only in spatial arrangement of groups (e.g., -OH groups, like D-glu,
D-man, etc.)
ENANTIOMERS = mirror image isomers
(e.g., corresponding D- vs L- sugars)
ANOMERS = isomers differing only in position of -OH groups at anomeric carbons (i.e., a- vs b- isomers)
EPIMERS = Stereoisomers differing in position of -OH groups at only one asymmetric carbon

13. CHO Classification I
Monosaccharides
Oligosaccharides
Polysaccharides

14. CHO Classification II Monosaccharides Open chain Cyclic forms
Planar, Haworth projection
3-dimensional

15. D-glucose & b -D-glucopyranoseH O
CH2OH OH 6 1 O
CH2OH OH 2 5 3 4 1 4 2 5 3 6
Fischer Projection
Haworth Projection

16. b -D-glucopyranose 6 4 5 2 1 3

17. CHO Classification III
Monosaccharides
Open chain
Cyclic forms
Planar, Haworth projection
3-dimensional
5 and 6 carbon most common

18. CHO Classification IV Oligosaccharides Disaccharides Sucrose Maltose
Lactose
Higher Oligosaccharides

19. CHO Classification V Polysaccharides > 20 monosaccharide units
Homo- and heteroglycans
Linear
Branched

20. Linear vs Branched PolymersRE O RE
linear
branched
Mannose
“backbone”
Substituted
Galactose
“side groups”

21. CHO Metabolism I Contributions to diet Major source of calories
4 Kcal/g
Texture, sweetness
Simple vs complex CHOs

22. CHO Metabolism II Enzyme activity Main means of digestion
On specific sugars

23. CHO Metabolism III Dietary fiber Indigestible polysaccharides
Function of
Sweetness
Positives
Negatives

24. Carbohydrates in Foods
“Naturally” present
3/4 of dry weight
Sucrose
Fruit
Cereals
Animal products
Added CHOs
Glycemic Index (Response)

25. Free Sugars in Fruit (% Fresh vs (Dry) Basis)

26. Free Sugars in Vegetables (% Fresh vs (Dry) Basis Basis)

27. Sugars in Common Foods

28. Carbohydrate Structure I
Monosaccharides
Glycosides
Oligosaccharides
Polysaccharides

29. Carbohydrate Structure II
Monosaccharides
Important ones
D-glyceraldehyde source
Aldoses & Ketoses
Isomerization

30. *= new asymetric Aldoses O O O O O O O O O O O O O O O = CHO = CH2OH
center
Rosanoff
Shorthand O
D-Triose
Aldoses
O = CHO
= CH2OH
= OH O O
Fig 3.3, p 86
D-Glycerose * *
D-Tetroses
D-Erythrose
D-Threose
D-Pentoses O O O O * * * *
D-Arabinose
D-Xylose
D-Lyxose
D-Ribose
D-Hexoses O O O O O O O * * * * * * * *
D-Allose
D-Altrose
D-Glucose
D-Mannose
D-Gulose
D-Idose
D-Galactose
D-Talose

31. R C
(H)(OH) O
R = H or CH2OH O
D-Tetrose
(D-Threose)
Sacharose group

32. Ketoses 1
CH2OH 2 C O O OH C 3 4 C OH 5 C OH 6
CH2OH
D-Fructose

33. Dihydroxyacetone (DHA)
Ketoses
CH2OH C O
Triulose
Tetruloses
Pentuloses
Hexuloses
Dihydroxyacetone (DHA)
CH3 C O
D-Erythrulose
D-glycero-Tetrulose O
Acetone * O O
D-Ribulose
D-erythro-Pentulose
D-Xylulose
D-threo-Pentulose * * O O O O * * * *
D-Psicose
D-Fructose
D-Sorbose
D-Tagatose
(D-ribo-Hexulose)
(D-arabino-Hexulose)
(D-xylo-Hexulose)
(D-xylo-Hexulose)
(D-lyxo-Hexulose)

34. Carbohydrate Structure III
Monosaccharides
Important ones
D-glyceraldehyde source
Isomerization
Involves both carbonyl and adjacent hydroxyl groups (i.e., on the a-carbon)

35. Monosaccharide isomerization trans-enediol (key intermediate)
CH2OH C OH O H
CH2OH C
O-H OH H
CH2OH OH C O H
D-Fructose
trans-enediol (key intermediate)
D-Glucose
CH2OH C HO OH O H
CH2OH C OH H
trans-enediol
D-Mannose
Fig 3.5, p 88