Organic chemistry II
Zdeněk Friedl
Chapter 25
Saccharides
Solomons & Fryhle: Organic
Chemistry 8th Ed., Wiley 2004
Saccharides
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classification of saccharides, monosaccharides
structural formulas for monosaccharides
mutarotation
glycosides (acetals), ethers and esters of monosaccharides
oxidation and reduction of monosaccharides, osazones
deoxy monosaccharides
disaccharides
polysaccharides
2
Classification of monosaccharides I
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Classification of monosaccharides II
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Summary of the D-aldohexoses
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Structural formulas for monosaccharides
D-(+)-Glucose
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Mutarotation of
D-(+)-glucose
7
Formation of anomeric GLYCOSIDES
(acetals)
8
Glykoside Salicin
COOH
COOH
OH
OCOCH3
9
Formation of ethers
10
Formation of esters
11
Oxidation of aldoses I
ALDONIC acids
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Oxidation of aldoses II
ALDURONIC acids
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Oxidation of aldoses III
ALDARIC acids
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Reduction of monosaccharides - ALDITOLS
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Reaction of monosaccharides with phenylhydrazine
OSAZONES
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Deoxy-monosaccharides
contained in DNA
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Nonreducing disaccharides (+)-Sucrose
α-D-glucopyranosyl-β-D-fructofuranoside
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Reducing disaccharides (+)-Maltose
4-O-(α-D-glucopyranosyl)-β-D-glucopyranose
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Reducing disaccharides (+)-Lactose
4-O-(β−D-galactopyranosyl)-β-D-glucopyranose
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Polysaccharides
Amylose
α-(1g 4) glycosidic linkages create an amylose chain
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Polysaccharides
Amylose
α-(1g 4) linkages cause the shape of left-handed helix
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Polysaccharides
Amylopectin
α-(1g 6) linkages branch the amylopectine chains
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Polysaccharides
Cellulose
the chain is created by β-(1g 4) glycosidic linkages
24
Polysaccharides
Cellulose
Cellulose chains create the sheets which are connected by hydrogen bond
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Bioactive saccharides
antibiotic Streptomycin
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A summary of monosaccharide reactions
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