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Western University
Chemistry 2223B
James Wisner

Chemistry 2223bWinter 201314Western University Topic 4 Carbohydrates This chapter discusses the fundamental chemistry and properties of carbohydrates emphasizing on monosaccharides The mechanistic chemistry of the metabolism of glucose into pyruvate glycolysis is also introduced Background material that is important includes o Stereochemistry enantiomers and diastereomers Fischer projections o Reactions of alcohols carbonyl compounds and carboxylic acidsNucleophilic additionNucleophilic substitutionOxidation and reduction Carbohydrates2 A Biological Significance and Categories of CarbohydratesCarbohydrates are the most abundant naturally occurring class of biomolecules they constitute half of the worlds biomass dry weightThey are made primarily by plants via photosynthesis In turn we consume them for energy Hence they serve as a mechanism of energy storage Light energyCOHOcarbohydratesO222Carbohydrates also have structural roles such as cellulose and chitin OOOH They are also components of CHOH2OHsome drugs such as salicin OHOHOCHOH2willow bark and adriamycin OHOOHStreptomyces achromogenes OOOCH3SalicinHCO3NH2OHAdriamycinCarbohydrates3Carbohydrates are found as components of not only small biomolecules but also in large highmolecularweight biopolymers These include o Glycoproteinsproteins with short branched carbohydrate chains bonded to the side chains of the amino acidsUsed for receptors recognition and celltocell interactionsExample bloodgroup antigens A and B o Proteoglycans mucopolysaccharidesproteins with long linear carbohydrate chains bonded to the side chains of the amino acidsTypically found in connective tissue and cartilage o Peptidoglycanslong linear carbohydrates crosslinked by short oligopeptidesTypically found in bacterial cell walls o Lipopolysaccharidesfatty acids linked to carbohydratesTypically found in the outer envelope of Gramnegative bacteria
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