Acarviosin

 Acarviosin is a sugar composed of cyclohexitol linked to a 4-amino-4,6-dideoxy-D-glucopyranose. Acarviosin is part of the potent α-amylase inhibitor acarbose and its derivatives. The nitrogen atom binds to α-amylase more tightly than the natural substrate making it more potent than other inhibitors. Several other acarviosin-containing α-amylase inhibitors have been found in microbes including isovalertatins [1] and butytatins [2] from Streptomyces luteogriseus and longer oligosaccharides from Streptomyces coelicoflavus.[3]

Acarviosin
Acarviosin.svg
Names
IUPAC name
Methyl 4,6-dideoxy-4-{[(1R,4S,5R,6R)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino}-α-D-glucopyranoside
Identifiers
CAS Number
  • 80943-41-5 ☒
3D model (JSmol)
  • Interactive image
ChemSpider
  • 2340579 check
PubChem CID
  • 3083346
CompTox Dashboard (EPA)
  • DTXSID30161850 Edit this at Wikidata
InChI
  • InChI=1S/C14H25NO8/c1-5-8(11(19)13(21)14(22-2)23-5)15-7-3-6(4-16)9(17)12(20)10(7)18/h3,5,7-21H,4H2,1-2H3/t5-,7-,8-,9+,10-,11+,12-,13-,14+/m1/s1 check
    Key: KFHKERRGDZTZQJ-HHHVGSORSA-N check
  • InChI=1/C14H25NO8/c1-5-8(11(19)13(21)14(22-2)23-5)15-7-3-6(4-16)9(17)12(20)10(7)18/h3,5,7-21H,4H2,1-2H3/t5-,7-,8-,9+,10-,11+,12-,13-,14+/m1/s1
    Key: KFHKERRGDZTZQJ-HHHVGSORBI
SMILES
  • O[C@@H]2[C@@H](O)[C@H](N[C@@H]1/C=C(/CO)[C@H](O)[C@@H](O)[C@@H]1O)[C@H](O[C@@H]2OC)C
Properties
Chemical formula
C14H25NO8
Molar mass335.353 g·mol−1
Density1.488 g/mL
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

This article uses material from the Wikipedia article
 Metasyntactic variable, which is released under the 
Creative Commons
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