Saccharides Vladimíra Kvasnicová. SACCHARIDES (carbohydrates, glycides) = polyhydroxyaldehydes or polyhydroxyketones D-glucose D-fructose.

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Presentation transcript:

Saccharides Vladimíra Kvasnicová

SACCHARIDES (carbohydrates, glycides) = polyhydroxyaldehydes or polyhydroxyketones D-glucose D-fructose

GLUCOSE – central role The figures have been adopted from Harper´s Biochemistry a z spittle/organic/chiral_web/images/fig1_5d.gif (April 2007) spittle/organic/chiral_web/images/fig1_5d.gif chiral carbon

The figure is found at (April 2007)

The figure is found at (April 2007) number of isomers for n(C*) = 2 n n = 1, 2, 3,...

Classification of monosaccharides aldoses (-CHO)ketoses (>C=O) trioses (C3)glyceraldehydedihydroxyacetone tetroses (C4)erythroseerythrulose pentoses (C5)riboseribulose hexoses (C6)glucosefructose

Isomers of monosaccharides The figures have been adopted from Harper´s Biochemistry 1) D- and L- izomers = mirror images (enantiomers) nature important: D-monosaccharides

2) pyranoses and furanoses pyranoses: aldohexoses furanoses: fructose ribose glucopyranose predominates The figures have been adopted from Harper´s Biochemistry

3)  and  anomers only cyclic molecules during dissolving of a saccharide in water the equilibrium between anomers is established = mutarotation (optical rotation of anomers is not the same)  -D-Glc  -D-Glc The figure is found at (October 2007)

1)  -D-glucopyranose2)  -D-glucopyranose 5) D-glucose 3)  -D-glucofuranose 4)  -D-glucofuranose

4) aldo-/keto- isomers aldose / ketose glyceraldehyde / dihydroxyacetone ribose / ribulose glucose /fructose The figures have been adopted from Harper´s Biochemistry

5) epimers = isomers of saccharides differing in orientation of only one –OH group in space Man = 2-epimer of Glc Gal = 4-epimer of Glc The figures have been adopted from Harper´s Biochemistry

Gal is found in lactose (milk sugar) Gal and Man and their derivatives are found in heteroglycosides

Derivates of monosaccharides 1) sugar alcohols are formed by reduction of the carbonyl group glucose → glucitol (= sorbitol) fructose mannose → mannitol galactose → galactitol D-Glucitol

2) oxidation of saccharides produces acids: aldaric acids (glucaric) both C1 and C6 is oxidized = dicarboxylic a. aldonic acids (gluconic) oxidation of C1 alduronic (glucuronic) oxidation of C6

3) deoxysaccharides are formed by reduction of secondary –OH group 2-deoxy-D-ribose 4) amino saccharides contain one amino group instead of one –OH group D-glucose amine The figures have been adopted from Harper´s Biochemistry

The figure has been adopted from J.Koolman, K.H.Röhm / Color Atlas of Biochemistry, 2 nd edition, Thieme 2005 amino saccharides are often acetylated (found in heteroglycosides)

5) esters are formed by esterification with H 3 PO 4 (intermediates of metabolism) with H 2 SO 4 (found in proteoglycans) The figure has been adopted from J.Koolman, K.H.Röhm / Color Atlas of Biochemistry, 2 nd edition, Thieme 2005

6) glycosides are formed by reaction with alcohols or amines O-glycosidic bond (oligo and polysaccharides, connection to proteins) N-glycosidic bond (in nucleic acids, connection to proteins) The figure has been adopted from J.Koolman, K.H.Röhm / Color Atlas of Biochemistry, 2 nd edition, Thieme 2005

The figure is found at (October 2007) O-glycosidic bond

The figure is found at (October 2007) N-glycosidic bond Adenosine triphosphate (ATP) ribose

The figure has been adopted from J.Koolman, K.H.Röhm / Color Atlas of Biochemistry, 2 nd edition, Thieme 2005  -Glc(1 → 4)Gal  - Gal(1 → 4)Glc  -Glc(1 → 2)  - Fru DISACCHARIDES

POLYSACCHARIDES homopolysaccharides starch, glycogen, cellulose, inuline heteropolysaccharides glycoproteins, proteoglycans branched unbranched storage starch, glycogen, inuline structural cellulose, proteoglycans

amylose (maltose) n amylopectine STARCH (Glc) n The figures have been adopted from Harper´s Biochemistry

GLYCOGEN (Glc) n The figure is found at (October 2007) nonreducing end reducing end OH

CELLULOSE  -Glc(1 → 4)Glc The figures are found at (October 2007)

heteroglycosides = complex saccharides proteoglycans glycoproteins glycolipids „glycan“ = polysaccharide cellextracellular fluid The figure has been adopted from: J.Koolman, K.H.Röhm / Color Atlas of Biochemistry, 2 nd edition, Thieme 2005 bacteria

The figure is found at (October 2007) PROTEOGLYCANS core protein + glycosaminoglycans (GAG) (aminosugar-uronic acid) n

The figure has been adopted from J.Koolman, K.H.Röhm / Color Atlas of Biochemistry, 2 nd edition, Thieme 2005 GLYCOPROTEINS