Altrose
Stereo structural formula of (5R)-altrose
Stereo structural formula of (6R)-altropyranose
Names
Preferred IUPAC name
Altrose
Systematic IUPAC name
(2S,3R,4R)-2,3,4,5,6-Pentahydroxyhexanal
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4?,5+,6-/m1/s1 ☒N
    Key: GZCGUPFRVQAUEE-ZPQYLTHOSA-N ☒N
  • InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4-,5+,6?/m1/s1
  • InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4-,5+,6?/m1/s1
    Key: WQZGKKKJIJFFOK-RSVSWTKNSA-N
  • OCC(O)[C@@H](O)[C@@H](O)[C@H](O)C=O
  • O[C@@H]1[C@H](O)[C@H](OC(O)[C@H]1O)CO
Properties
C6H12O6
Molar mass 180.156 g·mol−1
Melting point 103 to 105 °C (217 to 221 °F; 376 to 378 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Altrose is an aldohexose sugar. D-Altrose is an unnatural monosaccharide. It is soluble in water and practically insoluble in methanol. However, L-altrose has been isolated from strains of the bacterium Butyrivibrio fibrisolvens.[1]

Altrose is a C-3 epimer of mannose. The ring conformation of α-altropyranoside is flexible compared to most other aldohexopyranosides, with idose as exception. In solution different derivatives of altrose have been shown to occupy both 4C1, OS2 and 1C4-conformations.[2]

Haworth projections of various forms of D-altrose
Haworth projections of various forms of D-altrose

References

  1. ^ US patent 4966845, Stack; Robert J., "Microbial production of L-altrose", issued 1990-10-30, assigned to Government of the United States of America, Secretary of Agriculture 
  2. ^ Immel, Stefan; Fujita, Kahee; Lichtenthaler, Frieder W. (1999). "Solution Geometries and Lipophilicity Patterns ofα-Cycloaltrin". Chemistry - A European Journal. 5 (11): 3185–3192. doi:10.1002/(SICI)1521-3765(19991105)5:11<3185::AID-CHEM3185>3.0.CO;2-W. ISSN 0947-6539.