Vicianin

Vicianin
Chemical structure of vicianin
Names
IUPAC name
(R)-[α-L-Arabinopyranosyl-(1→6)-β-D-glucopyranosyloxy](phenyl)acetonitrile
Systematic IUPAC name
(R)-Phenyl{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}acetonitrile
Other names
(R)-Vicianin
6-O-Arabinopyranosylglucopyranoside
β-Vicianoside
Identifiers
3D model (JSmol)
UNII
  • C1[C@@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@@H](C#N)C3=CC=CC=C3)O)O)O)O)O)O
Properties
C19H25NO10
Molar mass 427.406 g·mol−1
Related compounds
Related compounds
 amygdalin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Vicianin is a cyanogenic disaccharide.

The enzyme vicianin beta-glucosidase uses (R)-vicianin and H2O to produce mandelonitrile and vicianose. It is found in seeds of Vicia angustifolia.[1]

  1. ^ Ahn, Y. O.; Saino, H.; Mizutani, M.; Shimizu, B.-i.; Sakata, K. (2007). "Vicianin hydrolase is a novel cyanogenic beta-glycosidase specific to beta-vicianoside (6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside) in seeds of Vicia angustifolia". Plant and Cell Physiology. 48 (7): 938–47. doi:10.1093/pcp/pcm065. PMID 17548373.