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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
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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.

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Isomerism

For biosynthetic reasons, 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

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

General:	Aldose \| Ketose \| Pyranose \| Furanose
Geometry:	Triose \| Tetrose \| Pentose \| Hexose \| Heptose \| Cyclohexane conformation \| Anomer \| Mutarotation
Small/Large:	Glyceraldehyde \| Dihydroxyacetone \| Erythrose \| Threose \| Erythrulose \| Sedoheptulose
Trioses:	ketotriose \| Aldotriose
Tetroses:	Erythrulose \| Erythrose \| Threose
Pentoses:	Arabinose \| Deoxyribose \| Lyxose \| Ribose \| Ribulose \| Xylose \| Xylulose
Hexoses:	Glucose \| Galactose \| Mannose \| Gulose \| Idose \| Talose \| Allose \| Altrose \| Fructose \| Sorbose \| Tagatose \| Psicose \| Fucose \| Rhamnose
Disaccharides:	Sucrose \| Lactose \| Trehalose \| Maltose
Polymers:	Glycogen \| Starch (Amylose \| Amylopectin) \| Cellulose \| Chitin \| Stachyose \| Inulin \| Dextrin
Glycosaminoglycans:	Heparin \| Chondroitin sulfate \| Hyaluronan \| Heparan sulfate \| Dermatan sulfate \| Keratan sulfate
Aminoglycosides:	Kanamycin \| Streptomycin \| Tobramycin \| Neomycin \| Paromomycin \| Apramycin \| Gentamicin \| Netilmicin \| Amikacin