Arabinose

Arabinose
Identifiers
CAS number 147-81-9 Y, 10323-20-3 (D) Y, 5328-37-0 (L) Y
PubChem 5460291
ChemSpider 59687 Y
EC-number 205-699-8
ChEBI CHEBI:46983 Y
Jmol-3D images Image 1
Image 2
Properties[1]
Molecular formula C5H10O5
Molar mass 150.13 g mol−1
Appearance Colorless crystals as prisms or needles
Density 1.585 g/cm3 (20 ºC)
Melting point

164-165 °C, 437-438 K, 327-329 °F

Solubility in water Soluble
Related compounds
Related aldopentoses Ribose
Xylose
Lyxose
 Y (verify) (what is: Y/N?)
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.

For biosynthetic reasons, most saccharides are almost always more abundant in nature as the "D"-form, or structurally analogous to D-glyceraldehyde.[note 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.[2]

D-Arabinose

α-D-Arabinofuranose

β-D-Arabinofuranose

α-D-Arabinopyranose

β-D-Arabinopyranose

Contents

Etymology

Arabinose gets its name from gum arabic, from which it was first isolated.[3]

Use

Arabinose is used as a culture medium for certain bacteria.

Notes

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

References

  1. ^ Weast, Robert C., ed (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-110. ISBN 0-8493-0462-8. 
  2. ^ Braun, Géza (1940), "D-Arabinose", Org. Synth. 20: 14, http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV3P0101 ; Coll. Vol. 3: 101 
  3. ^ Merriam Webster Dictionary