Chemistry:Valienamine

From HandWiki

Valienamine is an unsaturated amino sugar with the formula HOCH
2
(CHOH)
3
CHNH
2
)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. "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. June 2002. doi:10.1074/jbc.M202375200. PMID 11937512. 
  4. CID 193758 from PubChem