Valienamine

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
  • 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 Y
    Key: XPHOBMULWMGEBA-VZFHVOOUSA-N Y
  • 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).
N verify (what is YN ?)
Infobox references

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.

It found as a substructure of pseudooligosaccharides such as the antidiabetic drug acarbose and the antibiotic validamycin. It can be found in Actinoplanes species.

It is an intermediate formed by microbial degradation of validamycins.

Related compounds: valiolamine, validamine, and epi-valiolamine.

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