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25 • Summary

25 • Summary

Now that we’ve now seen all the common functional groups and reaction types, our focus has changed to looking at the major classes of biological molecules. Carbohydrates are polyhydroxy aldehydes and ketones. They are classified according to the number of carbon atoms and the kind of carbonyl group they contain. Glucose, for example, is an aldohexose, a six-carbon aldehydo sugar. Monosaccharides are further classified as either D sugars or L sugars, depending on the stereochemistry of the chirality center farthest from the carbonyl group. Carbohydrate stereochemistry is frequently depicted using Fischer projections, which represent a chirality center as the intersection of two crossed lines.

Monosaccharides normally exist as cyclic hemiacetals rather than as open-chain aldehydes or ketones. The hemiacetal linkage results from reaction of the carbonyl group with an –OH group three or four carbon atoms away. A five-membered cyclic hemiacetal is called a furanose, and a six-membered cyclic hemiacetal is called a pyranose. Cyclization leads to the formation of a new chirality center called the anomeric center and the production of two diastereomeric hemiacetals called alpha (α) and beta (β) anomers.

Much of the chemistry of monosaccharides is the familiar chemistry of alcohols and aldehydes/ketones. Thus, the hydroxyl groups of carbohydrates form esters and ethers. The carbonyl group of a monosaccharide can be reduced with NaBH4 to form an alditol, oxidized with aqueous Br2 to form an aldonic acid, oxidized with HNO3 to form an aldaric acid, oxidized enzymatically to form a uronic acid, or treated with an alcohol in the presence of acid to form a glycoside. Monosaccharides can also be chain-lengthened by the multistep Kiliani–Fischer synthesis and can be chain-shortened by Wohl degradation.

Disaccharides are complex carbohydrates in which simple sugars are linked by a glycoside bond between the anomeric center of one unit and a hydroxyl of the second unit. The sugars can be the same, as in maltose and cellobiose, or different, as in lactose and sucrose. The glycosidic bond can be either α (maltose) or β (cellobiose, lactose) and can involve any hydroxyl of the second sugar. A 1→4 link is most common (cellobiose, maltose), but others such as 1→2 (sucrose) are also known. Polysaccharides, such as cellulose, starch, and glycogen, are used in nature as structural materials, as a means of long-term energy storage, and as cell-surface markers.

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