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Carbohydrates and Nucleic Acids Help

By — McGraw-Hill Professional
Updated on Aug 16, 2011

Introduction

Carbohydrates (saccharides) are aliphatic polyhydroxyaldehydes (aldoses), polyhydroxyketones (ketoses), or compounds that can be hydrolyzed to them. The suffix -ose denotes this class of compounds. The monosaccharide D-(+)-glucose, an aldohexose, is formed by plants in photosynthesis and is converted to the polysaccharides cellulose and starch. Simple saccharides are called sugars, and typically have molecular formulae of Cn(H2O)n. Polysaccharides are hydrolyzable to monosaccharides. A carbohydrate is classified as either a ketose (if it contains a ketone carbonyl group) or an aldose (if it contains an aldehyde carbonyl group).

Fisher Projections. A simplest carbohydrate is glyceraldehyde. It is an aldotriose, since it is a 3-carbon aldehyde. It is common to draw carbohydrates in a Fisher projection, in which the carbon chain is drawn vertically on the page (aldehyde at top), and each stereogenic center is arranged so that the carbon chain is oriented back into the page. The substituents (hydrogen and hydroxyl) are drawn horizontally. The example below is D-glyceraldehyde.

Introduction

Introduction

Glucose is an aldohexose, so it is a 6-carbon aldehyde. The naturally occuring enantiomer, D-glucose, is shown here. The designation D stems from the last stereogenic center in the chain. If in the Fisher projection, the hydroxyl of the last stereogenic center (in the box) is on the right side of the chain, it is designated D. If that hydroxyl is on the left, the molecule is an L-sugar.

Mutarotation. Nearly all carbohydrates are chiral, so they rotate planepolarized light either clockwise (+) or counterclockwise (–). Naturally occurring (+)-glucose is obtained in two forms: mp = 146 °C, [α]D = +112° and mp = 150 °C, [α]D = +19°. The specific rotation of each form of glucose changes (mutarotates) in water, and both reach a constant value of +52.7°. This phenomenon stems from the formation and equilibration of intramolecular hemiacetals. Carbohydrates that form 5-membered ring acetals are known as furanoses and ones that form 6-membered ring acetals are known as pyranoses.

Introduction

The two stereoisomeric hemiacetals are known as anomers, and they differ in configuration at the new stereogenic center formed from the carbonyl carbon. The anomer with the new hydroxyl "up" is known as the β-anomer, while, the anomer with the new hydroxyl "down" is the α-anomer.

Chemical Reactions of Monosaccharides

The chemistry of monosaccharides is the chemistry of the component aldehydes, ketones, and alcohols that make up these molecules. One example of how the chemistry of carbohydrates is the same as the chemistry of ketones is in their reaction with NaBH4.

Reduction to Alditols. Both ketoses and aldoses can be reduced with NaBH4 to reduced forms, known as alditols. With ketoses, this often produces 2 diastereomeric alditols.

Chemical Reactions of Monosaccharides

Disaccharides

Disaccharides are acetals in which an OH of one monosaccharide (the aglycone, denoted A) is bonded to the anomeric C of a second monosaccharide, B. The disaccharide is a glycoside of B, involving the anomeric center of one carbohydrate and an alcohol (in this case another carbohydrate). For example, the α-1,4-linked glucose dimer below is maltose. Polysaccharides are sugar polymers, linked in the same kind of manner.

Disaccharides

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