25: Carbohydrates
This chapter is designed to provide you with an overview of the biologically important group of compounds known as carbohydrates. Many of the compounds you will encounter while studying this chapter may appear to have very complex structures, but much of their chemistry can be readily understood in terms of the concepts and reactions discussed in earlier chapters of the course.
The chapter begins with an explanation of the classification schemes used to simplify the study of carbohydrates. We make extensive use of Fischer projection formulas throughout the chapter. We place considerable emphasis on gaining an appreciation of the configurations of carbohydrates, particularly of the aldoses. We describe the disadvantages of representing monosaccharides by open-chain structures, and at this point, introduce you to cyclic representations—called Haworth projections—of these substances. We describe the mutarotation of glucose, explaining it in terms of the existence of anomers. We then examine some reactions of monosaccharides, including the formation of ethers and esters, the formation of glycosides, and reduction and oxidation. We discuss the structures of some common disaccharides and polysaccharides, and conclude the chapter with a brief explanation of the role played by carbohydrates in cell recognition.
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- 25.2: Depicting Carbohydrate Stereochemistry - Fischer Projections
- The wedge and dash notations we have been using are effective for drawing three-dimensional configurations on a two-dimensional surface,, but can be troublesome when applied to compounds having many chiral centers. Emil Fischer devised a simple notation that is still widely used. Fischer Projections allow us to represent 3D molecular structures in a 2D environment without changing their properties and/or structural integrity.
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- 25.6: Reactions of Monosaccharides
- Monosaccharides contain both alcohol and carbonyl functional groups. This allows monosaccharides to undergo many of the reactions typical for these functional groups. In particular, alcohols can be converted to esters, converted to ethers, converted to acetals, or oxidized. Carbonyls can be reacted with nucleophiles, be reduced to form alcohols, or be oxidized to form carboxylic acids.