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Pentose
In chemistry, a pentose is a monosaccharide (simple sugar) with five carbon atoms. The chemical formula of many pentoses is C
5H
10O
5, 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.
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 C
5H
10O
5-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. These forms occur in pairs of optical isomers, generally labelled "D" or "L" by conventional rules (independently of their optical activity).
The aldopentoses have three chiral centers; therefore, eight (23) different stereoisomers are possible.
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.
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Pentose
In chemistry, a pentose is a monosaccharide (simple sugar) with five carbon atoms. The chemical formula of many pentoses is C
5H
10O
5, 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.
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 C
5H
10O
5-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. These forms occur in pairs of optical isomers, generally labelled "D" or "L" by conventional rules (independently of their optical activity).
The aldopentoses have three chiral centers; therefore, eight (23) different stereoisomers are possible.
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.