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Arabinose

From Wikipedia, the free encyclopedia
Arabinose
Names
IUPAC name
Arabinose
Systematic IUPAC name
arabino-Pentose[1]
Other names
Pectinose
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 205-699-8
UNII
  • InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4-,5+/m1/s1 checkY
    Key: PYMYPHUHKUWMLA-WDCZJNDASA-N checkY
  • InChI=1/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4-,5+/m1/s1
    Key: PYMYPHUHKUWMLA-WDCZJNDABW
  • O=C[C@@H](O)[C@H](O)[C@H](O)CO
  • C([C@H]([C@H]([C@@H](C=O)O)O)O)O
Properties[2]
C5H10O5
Molar mass150.13 g/mol
AppearanceColorless crystals as prisms or needles
Density1.585 g/cm3 (20 °C)
Melting point164 to 165 °C (327 to 329 °F; 437 to 438 K)
834 g/1 L (25 °C (77 °F))
−85.70·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
Related compounds
Ribose
Xylose
Lyxose
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Arabinose is analdopentose – amonosaccharide containing fivecarbonatoms, and including analdehyde (CHO)functional group.

Properties

[edit]

For biosynthetic reasons, most saccharides are almost always more abundant in nature as the "D"-form, or structurally analogous toD-glyceraldehyde.[note 1] However,L-arabinose is in fact more common thanD-arabinose in nature and is found in nature as a component of biopolymers such ashemicellulose andpectin.[3]

TheL-arabinose operon, also known as the araBAD operon, has been the subject of much biomolecular research. Theoperon directs thecatabolism of arabinose inE. coli, and it is dynamically activated in the presence of arabinose and the absence of glucose.[4]

A classic method for the organic synthesis of arabinose from glucose is theWohl degradation.[5]

D-Arabinose

α-D-Arabinofuranose
β-D-Arabinofuranose

α-D-Arabinopyranose
β-D-Arabinopyranose

Etymology

[edit]

Arabinose gets its name fromgum arabic, from which it was first isolated.[6]

Use in foods

[edit]

Originally commercialized as a sweetener, arabinose is aninhibitor ofsucrase, theenzyme that breaks downsucrose intoglucose andfructose in thesmall intestine.[7]

See also

[edit]

Notes

[edit]
  1. ^The D/L nomenclature does not refer to the molecule's optical rotation properties but to its structural analogy toglyceraldehyde.

References

[edit]
  1. ^"Appendix".
  2. ^Weast, Robert C., ed. (1981).CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, Florida: CRC Press. p. C-110.ISBN 0-8493-0462-8.
  3. ^Holtzapple, M.T. (2003). "HEMICELLULOSES".Encyclopedia of Food Sciences and Nutrition. pp. 3060–3071.doi:10.1016/B0-12-227055-X/00589-7.ISBN 9780122270550.
  4. ^Watson, James (2003).Molecular Biology of the Gene. p. 503.
  5. ^Braun, Géza (1940)."D-Arabinose".Organic Syntheses.20: 14;Collected Volumes, vol. 3, p. 101.
  6. ^Merriam Webster Dictionary
  7. ^Krog-Mikkelsen, Inger; Hels, Ole; Tetens, Inge; Holst, Jens Juul; Andersen, Jens Rikardt; Bukhave, Klaus (2011-08-01)."The effects of L-arabinose on intestinal sucrase activity: dose-response studies in vitro and in humans".The American Journal of Clinical Nutrition.94 (2):472–478.doi:10.3945/ajcn.111.014225.ISSN 1938-3207.PMID 21677059.
General
Geometry
Monosaccharides
Dioses
Trioses
Tetroses
Pentoses
Hexoses
Heptoses
Above 7
Multiple
Disaccharides
Trisaccharides
Tetrasaccharides
Other
oligosaccharides
Polysaccharides
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