Carbohydrate Technology

งานนำเสนอเรื่อง: "Carbohydrate Technology"— ใบสำเนางานนำเสนอ:

1 Carbohydrate Technology
Dudsadee Uttapap

2 References: Key words: -Carbohydrate structure -Monosaccharide
-Lecture

3 What is carbohydrate? Carbon + H2O
Polyhydroxy aldehydes, ketones and their derivatives, and the polymer derived from these compounds

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5

6 Aldose & Ketose

7 Carbon Formula/name aldose ketose 3 4 5 6 7 C3H6O3 C4H8O4 C5H10O5
Glyceraldehydes Erythrose Ribose xylose Glucose Galactose - Dihydroxyacetone Erythrulose Ribulose Xylulose Fructose Tagatose Sedoheptulose can be up to nine

8 Aldose

9 Ketose

10 D,L-isomers (stereochemical designation

11 isomer = 2n n = No. of chiral center

12 The D enantiomers of sugars predominate in nature

13 Enantiomers and Epimers

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15 Structural Representation
Acyclic system Fisher projections Wedge-Slash formula

16 Cyclic system Fischer VS Haworth Projection

17 Cyclization “Intramolecular hemiacetals/hemiketals”
Aldose containing at least 5 C or ketose containing at least 6 C

18 Cyclization of glucose

19 Cyclization of ribose

20 Glucose Fructose

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23 Cyclic sugar

24 Alpha-/beta-ANOMERS New chiral center 2 stereoisomer (anomers)

25 Chair conformations are generally more stable than boat conformations
Glucose conformation Chair conformations are generally more stable than boat conformations

26 Reducing/Nonreducing sugar
A reducing sugar has to have a free anomeric carbon

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28 Reducing power

29 Properties of Mutarotation
Reducing sugar ในสภาพสารละลายทุกตัวเป็น Optically active (rotate the plane of polarized light) เมื่อละลาย Reducing Sugar จะเห็นการเปลี่ยนแปลง Rotation กับ เวลา เรียก “Mutarotation” ตัวอย่าง น้ำตาล fructose ละลายน้ำ เริ่มต้น Specific Rotation ()D20 =  ที่จุดสมดุลย์ =  น้ำตาล glucose ละลายน้ำ เริ่มต้น Specific Rotation ()D20 =  ที่จุดสมดุลย์ = -52

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32 Open-chain < 1%

33 Glucose Derivatives

34 Amino sugar

35 Sugar acid

36 Sugar Phosphate

37 Sugar Alcohol

38 Glycosidic/acetal linkage
Glycoside Glycosidic/acetal linkage

39 Carbohydrate Nomenclature
(alpha)- and  (beta)-D-Glucopyranose [1,2] (alpha)- and  (beta)-D-Glucofuranose [3,4]

40 1,2,3,4,6-Penta-O-acetyl- (alpha) -D-Glucopyranose [5]
4-O-acetyl-1,2-di-O-benzoyl-6-O-p-tolylsulfonyl- (alpha) -D-galactopyranose [6]

41 1,6-Anhydro- (beta)-D-Glucopyranose [14]
4,6-O-Benzylidene- (beta) -D-Glucopyranose [7] 1,2:5,6-Di-O-isopropylidene- (alpha) -D-Glucopyranose [8] 1,6-Anhydro- (beta)-D-Glucopyranose [14]

42 Glycosides Methyl- (alpha) -D- mannopyranoside [9]
O-(6-O-Methyl- (alpha) -D-Galactopyranosyl)-(1 4)-  (alpha) -D-Galactopyranose [19]

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44 Methyl-6-Deoxy- (alpha) -D-
mannopyranoside [10] 6-Amino-6-deoxy- (alpha) -D- glucopyranose [11] 6-Deoxy-6-iodo- (beta) -D- galactopyranose [12]