Valienamine

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]

Quick facts Names, Identifiers ...

Valienamine

Names
Preferred IUPAC name (1S,2S,4R,6S)-6-Amino-4-(hydroxymethyl)cyclohex-4-ene-1,2,3-triol
Identifiers
CAS Number	38231-86-6 N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1230806 N
ChemSpider	168149 Y
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 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
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). N verify (what is YN ?) Infobox references

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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.