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Pentose - Wikipedia

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22 views4 pages

Pentose - Wikipedia

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Chandra Reddy
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Pentose

In chemistry, a pentose is a monosaccharide (simple sugar) with five carbon atoms.[1] The chemical
formula of many pentoses is C5H10O5, and their molecular weight is 150.13 g/mol.[2]

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.[3] 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.

Classification

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).
Aldopentoses

The aldopentoses have three chiral centers; therefore, eight (23) different stereoisomers are
possible.

D-Arabinose D-Lyxose D-Ribose D-Xylose

L-Arabinose L-Lyxose L-Ribose L-Xylose

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.

Ketopentoses

The 2-ketopentoses have two chiral centers; therefore, four (22) different stereoisomers are
possible. The 3-ketopentoses are rare.

D-Ribulose D-Xylulose

L-Ribulose L-Xylulose
Cyclic forms

The closed or cyclic form of a pentose forms when the carbonyl group reacts with a hydroxyl in
another carbon, turning the carbonyl into a hydroxyl and creating an ether bridge –O– between the
two carbons. This intramolecular reaction yields a cyclic molecule, with a ring consisting of one
oxygen atom and usually four carbon atoms; the cyclic compounds are then called furanoses, for
having the same rings as the cyclic ether tetrahydrofuran.[3]

The ring closure converts the carbonyl carbon into a chiral center, which may adopt either of two
configurations, depending on the position of the new hydroxyl. Therefore, each linear form can
produce two distinct closed forms, identified by prefixes "α" and "β".

Deoxypentoses

The one deoxypentose has two total stereoisomers.

D-Deoxyribose

L-Deoxyribose

Properties

In the cell, pentoses have a higher metabolic stability than hexoses.

A polymer composed of pentose sugars is called a pentosan.

Tests for pentoses

The most important tests for pentoses rely on converting the pentose to furfural, which then reacts
with a chromophore. In Tollens’ test for pentoses (not to be confused with Tollens' silver-mirror test
for reducing sugars), the furfural ring reacts with phloroglucinol to produce a colored compound;[4]
in the aniline acetate test with aniline acetate;[5] and in Bial's test, with orcinol.[6] In each of these
tests, pentoses react much more strongly and quickly than hexoses.

References

1. Pentose (http://www.merriam-webster.com/dictionary/pentose) , Merriam-Webster

2. "d-Ribose (https://pubchem.ncbi.nlm.nih.gov/compound/D-Ribose) ". PubChem compound


webpage, accessed on 2010-02-06.

3. Morrison, Robert Thornton; Boyd, Robert Neilson. Organic Chemistry (2nd ed.). Allyn and Bacon.
Library of Congress catalog 66-25695

4. Oshima, Kintaro; Tollens, B. (May 1901). "Ueber Spectral‐Reactionen des Methylfurfurols" (http
s://onlinelibrary.wiley.com/doi/10.1002/cber.19010340212) . Berichte der Deutschen
Chemischen Gesellschaft. 34 (2): 1425–1426. doi:10.1002/cber.19010340212 (https://doi.org/
10.1002%2Fcber.19010340212) . ISSN 0365-9496 (https://search.worldcat.org/issn/0365-94
96) .

5. Seager, Spencer L.; Slabaugh, Michael R.; Hansen, Maren S. (2016-12-05). Safety Scale
Laboratory Experiments (https://books.google.com/books?id=xfS5DQAAQBAJ&pg=PA358) .
Cengage Learning. p. 358. ISBN 9781337517140.

6. Pavia, Donald L. (2005). Introduction to Organic Laboratory Techniques: A Small Scale Approach
(https://books.google.com/books?id=ega5c11VHvkC&pg=PA447) . Cengage Learning.
p. 447. ISBN 0534408338.

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