Article · Wikipedia archive · Last revised Jul 9, 2026

Valienamine

Valienamine is an unsaturated amino sugar with the formula HOCH2(CHOH)3CHNH2)CH. It is classified also as a C-7 aminocyclitol. It is a potent inhibitor of glycosidase. It was first isolated by microbial degradation of validoxylamine.

Last revised
Jul 9, 2026
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Source
Wikipedia ↗
Valienamine
Chemical structure of valienamine
Chemical structure of valienamine source ↗
Names
Preferred IUPAC name
(1S,2S,4R,6S)-6-Amino-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • 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/s1 checkY
    Key: XPHOBMULWMGEBA-VZFHVOOUSA-N checkY
  • 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/s1
    Key: XPHOBMULWMGEBA-VZFHVOOUBJ
  • O[C@@H]1\C(=C/[C@H](N)[C@H](O)[C@H]1O)CO
Properties
C7H13NO4
Molar mass 175.184 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)

Valienamine is an unsaturated amino sugar with the formula HOCH2(CHOH)3CHNH2)CH. It is classified also as a C-7 aminocyclitol. It is a potent inhibitor of glycosidase. It was first isolated by microbial degradation of validoxylamine.1

It found as a substructure of pseudooligosaccharides such as the antidiabetic drug acarbose2 and the antibiotic validamycin. It can be found in Actinoplanes species.3

It is an intermediate formed by microbial degradation of validamycins.4

Related compounds: valiolamine, validamine, and epi-valiolamine.

References

References

  1. Chen, Xiaolong; Fan, Yongxian; Zheng, Yuguo; Shen, Yinchu (2003). "Properties and Production of Valienamine and Its Related Analogues". Chemical Reviews. 103 (5): 1955–1978. doi:10.1021/cr0102260. PMID 12744697.
  2. 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.
  3. 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.
  4. CID 193758 from PubChem
External links