Jump to content

L-Streptose

From Wikipedia, the free encyclopedia
(Redirected from Streptose)
l-Streptose
Names
IUPAC name
5-Deoxy-3-C-formyl-α-l-lyxofuranose
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C6H10O5/c1-3-6(10,2-7)4(8)5(9)11-3/h2-5,8-10H,1H3/t3-,4-,5+,6+/m0/s1
    Key: PSLNNVPHIJQGRF-UNTFVMJOSA-N
  • C[C@H]1[C@@]([C@H]([C@@H](O1)O)O)(C=O)O
Properties
C6H10O5
Molar mass 162.141 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

l-Streptose is a branched monosaccharide similar to apiose in structure. l-Streptose is one of the sugars in streptomycin, an aminoglycoside antibiotic that has toxic effects in the kidney and other side effects.

l-Streptose has been prepared from a carbohydrate derivative.[1] The protected monosaccharide was reacted with an organolithium sulfur compound and then catalytically hydrolyzed to produce l-streptose.

References

[edit]
  1. ^ Block E. "Organic Chemistry: Reactions of Organosulfur Compounds", vol. 37, page 71.