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Concept
Pentose
Résumé
In chemistry, a pentose is a monosaccharide (simple sugar) with five carbon atoms. The chemical formula of many pentoses is C5H10O5, and their molecular weight is 150.13 g/mol.
Pentoses are very important in biochemistry. Ribose is a constituent of RNA, and the related molecule, deoxyribose, is a constituent of DNA. Phosphorylated pentoses are important products of the pentose phosphate pathway, most importantly ribose 5-phosphate (R5P), which is used in the synthesis of nucleotides and nucleic acids, and erythrose 4-phosphate (E4P), which is used in the synthesis of aromatic amino acids.
Like some other monosaccharides, pentoses exist in two forms, open-chain (linear) or closed-chain (cyclic), that easily convert into each other in water solutions. The linear form of a pentose, which usually exists only in solutions, has an open-chain backbone of five carbons. Four of these carbons have one hydroxyl functional group (–OH) each, connected by a single bond, and one has an oxygen atom connected by a double bond (=O), forming a carbonyl group (C=O). The remaining bonds of the carbon atoms are satisfied by six hydrogen atoms. Thus the structure of the linear form is H–(CHOH)x–C(=O)–(CHOH)4-x–H, where x is 0, 1, or 2.
The term "pentose" sometimes is assumed to include deoxypentoses, such as deoxyribose: compounds with general formula C5H10O5-y that can be described as derived from pentoses by replacement of one or more hydroxyl groups with hydrogen atoms.
The aldopentoses are a subclass of the pentoses which, in the linear form, have the carbonyl at carbon 1, forming an aldehyde derivative with structure H–C(=O)–(CHOH)4–H. The most important example is ribose. The ketopentoses instead have the carbonyl at positions 2 or 3, forming a ketone derivative with structure H–CHOH–C(=O)–(CHOH)3–H (2-ketopentose) or H–(CHOH)2–C(=O)–(CHOH)2–H (3-ketopentose). The latter is not known to occur in nature and are difficult to synthesize.
In the open form, there are eight aldopentoses and four 2-ketopentoses, stereoisomers that differ in the spatial position of the hydroxyl groups.
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