Valienamine

Valienamine is a C-7 aminocyclitol found as a substructure of pseudooligosaccharides such as the antidiabetic drug acarbose[1] and the antibiotic validamycin. It can be found in Actinoplanes species.[2]

Valienamine

Names
IUPAC name (1S,2S,3R,6S)-6-Amino-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol
Identifiers
CAS Number	38231-86-6
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1230806
ChemSpider	168149
PubChem CID	193758
CompTox Dashboard (EPA)	DTXSID80191622
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/s1 Key: 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/s1 Key: XPHOBMULWMGEBA-VZFHVOOUBJ
SMILES O[C@@H]1\C(=C/[C@H](N)[C@H](O)[C@H]1O)CO
Properties
Chemical formula	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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Infobox references

It is an intermediate formed by microbial degradation of validamycins.[3]

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

• Valienamine on chemblink.com