Valienamine

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Valienamine
Chemical structure of valienamine
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
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  • 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
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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).

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

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