1. Lecture VIII Oligosaccharides II
Individual Disaccharides
Higher Oligosaccharides
Lecture #8 - Oligosaccharides II
Will cover
...Individual Disaccharides (mainly sucrose)
…Higher Oligosaccharides

2. Individual Disaccharides Maltose
CH2OH OH HO OH OH
a-D-glucopyranosyl-(1->4)-a-D-glucopyranose
a-Maltose
Source
Enzyme treatments
Reactions
Uses

3. Starch IV (Digestability)
Limit Dextrin is left
b-Amylase activity on Amylopectin, with formation of Maltose and a high MW Limit Dextrin (Advances in Enzymol., 12, 394 (1951))

4. Individual Disaccharides Lactose
CH2OH OH HO
b-D-galactopyranosyl-(1-4)-a-D-glucopyranose
a-Lactose
Source
Biological (milk – Human = 7%, cow & goat = 4.5 – 4.8%)
Lactobacillus bifidus = MO of intestinal flora of breast-fed infants
Uses
Metabolism

5. Individual Disaccharides Lactose
Source
Biological (milk)
Uses
Contributes body to foods
Enhances colors & flavors (Maillard).
Tablet filler or diluent
Major consumption – part of dairy pdts
Lactose crystalization = problems
Metabolism
Lactose crystals-
tomahawk shape

6. Individual Disaccharides Lactose
Source
Biological (milk)
Uses
Metabolism
lactose D-glu + D-gal
lactase

7. Individual Disaccharides Lactose
Source
Biological (milk)
Uses
Metabolism
Lactose Intolerance
Occurance
Ways to overcome

8. Individual Disaccharides Sucrose
CH2OH OH HO 1 2 3 4 5 6
a-D-glucopyranosyl-(1-2)-b-D-fructofuranose O
CH2OH OH HO 1 2 3 4 5 6 or
History
Source
Biological
Commercial Products

9. Individual Disaccharides Sucrose
History
Source
Biological (photosynthesis)
Sucrose 1st
Other PSs – e.g., cellulose, starches, or other sugars
Commercial Products

10. Individual Disaccharides Sucrose
History
Source
Biological
Commercial Products
Cane sugar
MO’s - invertase enzyme
Some dextran
Beets

11. (Mechanical Crushing)
Sugar Cane Process
Sugar Cane
(Mechanical Crushing)
“Juice”
1) Ca(OH)2 2) Heat
Coagulum
1) Filter
2) Conc (red.
Pressure) (50%)
Crystals
(raw sugar)
Crystallization I II
Black Strap
Molasses
Mother liquor
1) Conc (red.
Pressure)
(Adapted from CHO Chem, for Food Scientists, Whistler & BeMiller)

12. Sugar Refining Process
Pure, white, table sugar
Clarified &, purified, Mother liquor
Crystals
(raw sugar)
Raw sugar
solution
water
ppt
Mother liquor
+ Lime &
Phosphate
1) Centrifuge 2) Filter thru diatomaceous earth/charcoal
Crystallization under red. pressure
(Adapted from CHO Chem, for Food Scientists, Whistler & BeMiller)

13. Individual Disaccharides Sucrose
History
Source
Biological
Commercial Products
Cane sugar
Beets

14. Neutralized Mother liquor Crystallize under red. pressure
Beet Sugar Process
(CaO)
Pure, white, table sugar
Neutralized Mother liquor
Beet
cosettes
water
Mother liquor
(alkaline)
+ Lime
1) Agitate for several hrs.
2) Bubble CO2
3) Filter
Crystallize under red. pressure
Counter-
current
extraction
Mother liquor,
ca. 12%
CaCO3
SO2
(Adapted from CHO Chem, for Food Scientists, Whistler & BeMiller

15. Individual Disaccharides Sucrose
Commercial Products
Cane sugar
Beets
Other Sugar Products
Brown sugar
Powdered sugar
Fondant sugar

16. The Chemical Safety & Hazard Investigation Board (CSB)
STEEP COSTS Fourteen workers died from an explosion of combustible dust in 2008 at this Imperial Sugar facility in Savannah, Ga., one of several accidents CSB investigated
The Chemical Safety & Hazard Investigation Board (CSB)
From C&E News, 2/15/10
STEEP COSTS Fourteen workers died from an explosion of combustible dust in 2008 at this
Imperial Sugar facility in Savannah, Ga., one of several accidents CSB investigated

17. Individual Disaccharides Sucrose
Commercial Products
Cane sugar
Beets
Other Sugar Products
Brown sugar
Powdered sugar
Fondant sugar
Transformed sugar
Liquid sugar

18. Individual Disaccharides Sucrose
History
Source
Properties of Crystals & Solutions I
Very soluble
Preservative
Humectant/Water binding
Cryoprotectant

19. Individual Disaccharides Sucrose
History
Source
Properties of Crystals & Solutions II
Very soluble
Preservative
Humectant/Water binding
Cryoprotectant

20. Function of Simple CHOs Hydrophilicity I

21. Individual Disaccharides Sucrose
History
Source
Properties of Crystals & Solutions III
Very soluble
Preservative
Humectant/Water binding
Cryoprotectant

22. Individual Disaccharides Sucrose - Structure6 5 2 3 1 4
Additional bond
in Crystals
CH2
In Solutions
CHO Chem, for Food Scientists, Whistler & BeMiller, p 56

23. Individual Disaccharides Sucrose
History
Source
Properties of Crystals & Solutions
Derivatives
Esters (e.g., “Olestra”)
Sucralose

24. Individual Disaccharides Sucrose
Derivatives
Esters
Sucralose O
CH2OH OH Cl
CH2Cl HO 1 2 3 4 5 6
Sucralose
CH2Cl
What’s this??

25. Individual Disaccharides Lactitol (Lactose Derivative)
Source
Reduction of Lactose
Food Uses
Metabolism O
CH2OH OH C HO
C-1
C-2
C-3
C-4
C-5
C-6
Kummel & Brokx, Cereal Foods World, pp , 9/01

26. Individual Disaccharides Lactose
CH2OH OH HO
b-D-galactopyranosyl-(1-4)-a-D-glucopyranose
a-Lactose
Source
Biological (milk)
Uses
Metabolism

27. CHO Classification IV Higher Oligosaccharides
Probiotic: “a live microbial feed sup-plement which beneficially affects the host by improving its intestinal microflora balance.”
Prebiotic: “a non-digestible food ingredient that beneficially affects the host by selectively promoting the growth and/or activity of one or a limited number of health-promoting bacterial in the colon, thus improving host health.”
REF: Imperial-Sensus lit. Inulin pdt called “Frutafit”

28. CHO Classification IV Higher Oligosaccharides
Sucrose portion
Kestose and Neosugar
FOS’s = (Fructo-oligosaccarides)

29. CHO Classification IV Higher Oligosaccharides
Inulin
n-1