Valienamine
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| Names | |
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| Preferred IUPAC name
(1S,2S,4R,6S)-6-Amino-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| 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
[edit]- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ CID 193758 from PubChem
External links
[edit]- Valienamine on chemblink.com Archived 2014-12-08 at the Wayback Machine
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