arabinose

Arabinose
IUPAC name	(2R,3S,4S)-2,3,4,5-Tetrahydroxypentanal
Identifiers
CAS number	[5328-37-0]
PubChem	5460291
SMILES	C([C@@H]([C@@H]([C@H](C=O)O)O)O)O
Properties
Molecular formula	C5H10O5
Molar mass	150.13 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

Arabinose is an aldopentose — a monosaccharide containing five carbon atoms, and including an aldehyde (CHO) functional group. It has chemical formula C₅H₁₀O₅ and a molar mass of 150.13 g/mol.

Isomerism

The chemical structure of D-arabinofuranose

For biosynthetic reasons, most saccharides are almost always more abundant in nature as the "D" form, or structurally analogous to D-(+)-glyceraldehyde.^[1] However, L-arabinose is in fact more common than D-arabinose in nature and is found in nature as a component of biopolymers such as hemicellulose and pectin. The L-arabinose operon is a very important operon in molecular biology and bioengineering.

A classic method for the organic synthesis of arabinose from glucose is the Wohl degradation.

References

1. ^ For sugars, the D/L nomenclature does not refer to the molecule's optical rotation properties but to its structural analogy to glyceraldehyde.

See also

• L-arabinose operon
• Deoxyribose
• Lyxose
• Ribose
• Ribulose
• Xylose
• Xylulose