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Carbohydrate Structure and Stereochemistry

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Lecture 14. Carbohydrate Structure and Stereochemistry ... Chitin (1 4)GlcNAc. Glycogen Branching. Glycogen Structure. Starch. Garrett and Grisham. ... – PowerPoint PPT presentation

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Title: Carbohydrate Structure and Stereochemistry


1
Lecture 14
  • Carbohydrate Structure and Stereochemistry

2
Carbohydrate Structure
3
Stereoisomers of Sugars
4
Aldoses
5
Some Common Monosaccharides
6
Epimers
  • Differ in configuration at only one carbon

7
Cyclic Forms of Sugars
Hemiacetal
O
OH
C
H

C
H
8
Cyclic Forms of Monosaccharides
9
Haworth Projections
10
Chair forms of glucose
11
Oxidation of Sugars
12
Glycosides Di- and Polysaccharides
13
Nomenclature of Di-, Polysaccharides
  • 1. Put non-reducing end to left
  • 2. Name as derivative of sugar at right
    (reducing) end
  • 3. Describe glycosidic bond(s)

14
Determining linkages
15
Determining linkages
By determining position of unmethylated OH
groups, deduce that bond was 1?4
16
Carbohydrate Analysis
  • Composition
  • 1. Strong acid hydrolysis
  • 2. Make volatile derivatives
  • 3. Separate by GC
  • Structure
  • 1. Linkages (sequence)
  • 2. Stereochemistry

17
Polysaccharides
  • Homopolysaccharide
  • Glycogen ?(1?4)Glucose (and branches)
  • Starch ?(1?4)Glucose (and branches)
  • Cellulose ?(1?4)Glucose
  • Chitin ?(1?4)GlcNAc

18
Glycogen Branching
19
Glycogen Structure
20
Starch
Garrett and Grisham. Biochemistry. 1995
21
Cellulose
22
Cellulose
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