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Exercise · Q17

Q.What type of glycosidic linkage joins the glucose units of cellulose, and how does this differ from the linkage in amylose?

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Cellulose is an unbranched, linear polymer of D-glucose units, joined together by β\beta-1,4-glycosidic linkages -- bonds running from C1 of one glucose unit to C4 of the next, in which the linkage oxygen sits on the 'beta' (above-the-ring) face at the anomeric carbon.

This is structurally very similar to amylose, which is also an unbranched chain of D-glucose units joined from C1 to C4 -- but amylose's linkage is instead an α\alpha-1,4-glycosidic linkage, with the linkage oxygen on the opposite, 'alpha' (below-the-ring) face. So the two linkages connect exactly the same pair of ring carbons (C1 and C4); the only difference is the stereochemical orientation (α\alpha versus β\beta) at the anomeric carbon forming the bond. This single stereochemical difference, small as it looks on paper, has a large structural consequence: it forces the β\beta-linked cellulos …

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