Vicine

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Vicine
Vicine.png
Names
IUPAC name
2,6-diamino-5-[(2S,3R,4S,5S,6R)- 3,4,5-trihydroxy-6-(hydroxymethyl)- 2-tetrahydropyranyl]oxy]-1H- pyrimidin-4-one
Identifiers
152-93-2 N
ChemSpider 82575 YesY
Jmol-3D images Image
PubChem 91446
Properties
C10H16N4O7
Molar mass 304.25 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

Vicine is an alkaloid glycoside found in fava beans.[1] Vicine is toxic, causing the disease favism, in individuals who have a hereditary loss of the enzyme glucose-6-phosphate dehydrogenase. Divicine is the name of the aglycone of vicine. Fava beans also contain the related 6-hydroxy- alkaloid glycoside covicine, whose aglycone is isouramil.

Vicine was first isolated by Heinrich Ritthausen. Classified as a pyrimidine, its structure and that of divicine has been described.[2] The formation in Vicia Faba of vicine and covicine has been investigated.[3]

References[edit]

  1. ^ Variability of Amino Acids, Protein, Vicine and Convicine in Vicia faba (L) Cultivars. Vincenzo Lattanzio, Vito V. Bianco, Giuseppe Crivelli and Vito Miccolis, Journal of Food Science, Volume 48, Issue 3, pages 992–993, May 1983 doi:10.1111/j.1365-2621.1983.tb14950.x
  2. ^ Aaron Bendich & Grace C. Clements (1953) "A revision to the structural formation of vicine and its pyrimidine aglucone, divicine", Biochimica et Biophysica Acta
  3. ^ E. G. Brown & F. M. Roberts (1972) "Formation of Vicine and Covicine by Vicia Faba", Phytochemistry 11:3203–6

External links[edit]