1. Lecture II Ring Forms, Glycosides
Indredients: NaAlginate; CaCl2; Color; ground glass; sucrose; bakers’ yeast.

2. Carbohydrate Structure III
Monosaccharides
Important ones
D-glyceraldehyde source
Straight chain does not explain all Rxs
Ring formation
Mutarotation
Haworth projection

3. CH3OH R C OH H OCH3 HOCH3 H C O R R C H2O H OCH3 .. RING FORMATION + +
Hemiacetal R
RING FORMATION R C
H2O H
OCH3 +
“Full” Acetal

4. RING FORMATION H O C CH2OH OH H O HO C CH2OH CH2OH CH2OH O C : OH H O6
CH2OH C OH O 5 4 3 2 1 H
CH2OH 5 C OH 3 2 1 H 4 HO O 6 O
CH2OH OH 6 5 4 3 2 1 6
CH2OH 5 C O OH 3 2 1 H 4 HO : O
Fig 3.7, p 88

5. b -D-glucopyranose 1 5 4 3 2 6
Fig 3.11, p 90

6. Glucose Anomers: Hemiacetals Reducing sugars Mutarotate
CH2OH OH 6 5 4 3 2 1
Ring opens here -
Mutarotation 1 C OH 2 C OH O OH C 3 4 C OH 5 C 6
CH2OH
a-D-Glucose (m.p. 146o, [a] = +112o) or
Equilb = 53o
Fischer projection
of hemiacetal ring
b-D-Glucose (m.p. 150o, [a] = +19o)

7. Glucose Equilibrium Cpds
Fig 3.12, p 91
a-D-glucofuranose
a-D-glucopyranose
0.003%
D-glucose
(aldehydo-D-glucose)
b-D-glucofuranose
b-D-glucopyranose
Possible isomers of D-glucose in aqueous solution

9. { HAWORTH PROJECTION * CH2OH D- O L- a (L-) b (D-) OH a (D-) b (L-)6 5 4 3 2 1 D- L- {
a (L-)
b (D-)
a (D-)
b (L-)
a-D-GLUCOSE
(a-D-Glucopyranose)

10. The Furanose Ring O OH
HOH2C 1 2 3 4 5
a-L-Arabinofuranose

11. C-5 EPIMERS = = Epimers = Stereoisomers differing in position of
D-MANNOSE
L-GULOSE
CH2OH O O O O
CH2OH = = OH OH OH OH OH OH
Epimers = Stereoisomers differing in position of
-OH groups at only one asymmetric
carbon (in this case, at C-5)

12. b-L-Galactopyranose/furanoseOH O
CH2OH OH o
CH2OH C O OH O

13. C-5 EPIMERS - Effect of bulky group1 2 3 4 5 6
b-D-Mannopyranosyluronic acid unit,
4C1 Conformation

14. C-5 EPIMERS - Effect of bulky group a-L-Gulopyranosyluronic acid6 1 4 3 2
a-L-Gulopyranosyluronic acid
unit - 1C4 conformation

15. Carbohydrate Structure IV
Glycosides
Alcohol + acid, - H2O
Physiological function
Base stable, acid labile
Rx with other sugars

16. Glycosides alkyl D-glucopyranoside D-glucose (D-glucopyranose)
Hemiacetal
linkage
aglycon
CH2OH O
CH2OH OH OR
+ H2O
alkyl
D-glucopyranoside O
+ ROH H+ OH OH
“Full” acetal
linkage OH OH
D-glucose
(D-glucopyranose)

17. Function of Simple CHOs in Foods I
Reactions with other Ingredients
Water (hydrophilicity)
Flavors
Sweeteners
Alcohols
Bulking Agents

19. Sugar Alcohols; Sweetness

20. Function of Simple CHOs in Foods II
Bulking Agents
Maltodextrins (DE < 20)
Maltrin MO40 – from corn
Instant N-Oil – from tapioca
Paselli SA1 – from potato
Oatrim – from oat bran & flour
Polydextrose (to be covered later)

21. NEOSORB P60 sorbitol (Roquette) 50.00 5.000
NONFAT, NO SUGAR ADDED, SOFT SERVE ICE CREAM WITH PRIMACEL FOOD
CELLULOSE PRODUCT, SIMPLESSE* 500 AND NUTRASWEET* CUSTOM LIQUID 50
PRODUCT FORMULATION SS-7822
This formulation contains 27.5% total solids, 13.4% MSNF, 0.59% fat and no
added sugars. There is <0.5 g of fat per 80 g serving, qualifying the
formulation for the nonfat descriptor. This product is a good clean base for
a variety of flavors including vanilla.
QUANTITY
INGREDIENTS GRAMS PERCENT
Skim milk
NEOSORB P60 sorbitol (Roquette)
LITESSE polydextrose (Cultor)
Milk solids, nonfat
M180 maltodextrin (GPC)
SIMPLESSE 500 mircoparticulated whey
protein concentrate
Cream, 40% butterfat
PrimaCel food cellulose product
NUTRASWEET Custom Liquid
DM Freeze 75K emulsifier blend
Cellulose gum, 99-7HF (Hercules)
Flavoring to suit to suit
g %