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Valienamine

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Valienamine
Chemical structure of valienamine
Chemical structure of valienamine
Names
Preferred IUPAC name (1S,2S,4R,6S)-6-Amino-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H13NO4/c8-4-1-3(2-9)5(10)7(12)6(4)11/h1,4-7,9-12H,2,8H2/t4-,5+,6-,7-/m0/s1Key: XPHOBMULWMGEBA-VZFHVOOUSA-N
  • InChI=1/C7H13NO4/c8-4-1-3(2-9)5(10)7(12)6(4)11/h1,4-7,9-12H,2,8H2/t4-,5+,6-,7-/m0/s1Key: XPHOBMULWMGEBA-VZFHVOOUBJ
SMILES
  • O1\C(=C/(N)(O)1O)CO
Properties
Chemical formula C7H13NO4
Molar mass 175.184 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Valienamine is a C-7 aminocyclitol found as a substructure of pseudooligosaccharides such as the antidiabetic drug acarbose and the antibiotic validamycin. It can be found in Actinoplanes species.

It is an intermediate formed by microbial degradation of validamycins.

References

  1. Laube, Heiner (March 2002). "Acarbose An Update of Its Therapeutic Use in Diabetes Treatment". Clinical Drug Investigation. 22 (3): 141–156. doi:10.2165/00044011-200222030-00001.
  2. Zhang CS, Stratmann A, Block O, et al. (June 2002). "Biosynthesis of the C(7)-cyclitol moiety of acarbose in Actinoplanes species SE50/110. 7-O-phosphorylation of the initial cyclitol precursor leads to proposal of a new biosynthetic pathway". J. Biol. Chem. 277 (25): 22853–62. doi:10.1074/jbc.M202375200. PMID 11937512.
  3. CID 193758 from PubChem

External links


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