Valienamine

Last updated
Valienamine
Chemical structure of valienamine Valienamine.svg
Chemical structure of valienamine
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
PubChem CID
  • 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 Yes check.svgY
    Key: XPHOBMULWMGEBA-VZFHVOOUSA-N Yes check.svgY
  • 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).
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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 acarbose [2] 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

  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


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