Vicine

Vicine
Names
IUPAC name
2,6-Diamino-5-(β-D-glucopyranosyloxy)pyrimidin-4(1H)-one
Systematic IUPAC name
2,6-Diamino-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}pyrimidin-4(1H)-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.283 Edit this at Wikidata
UNII
  • InChI=1S/C10H16N4O7/c11-7-6(8(19)14-10(12)13-7)21-9-5(18)4(17)3(16)2(1-15)20-9/h2-5,9,15-18H,1H2,(H5,11,12,13,14,19)/t2-,3-,4+,5-,9+/m1/s1 checkY
    Key: KGNGTSCIQCLKEH-SYCVNHKBSA-N checkY
  • InChI=1/C10H16N4O7/c11-7-6(8(19)14-10(12)13-7)21-9-5(18)4(17)3(16)2(1-15)20-9/h2-5,9,15-18H,1H2,(H5,11,12,13,14,19)/t2-,3-,4+,5-,9+/m1/s1
    Key: KGNGTSCIQCLKEH-SYCVNHKBBM
  • O=C2\N=C(\N)NC(=C2/O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)/N
Properties
C10H16N4O7
Molar mass 304.259 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 checkY☒N ?)

Vicine is an alkaloid glycoside found mainly in fava beans, which are also called broad beans (Vicia faba).[1] Vicine is toxic in individuals who have a hereditary loss of the enzyme glucose-6-phosphate dehydrogenase. It causes haemolytic anaemia, called favism. The formation of vicine in Vicia faba has been studied, but this natural formation has not yet been found.[2][3]

  1. ^ Lattanzio V, Bianco VV, Crivelli G, Miccolis V (May 1983). "Variability of Amino Acids, Protein, Vicine and Convicine in Vicia faba (L) Cultivars". Journal of Food Science. 48 (3): 992–993. doi:10.1111/j.1365-2621.1983.tb14950.x.
  2. ^ Mager, J.; Razin, A.; Herschko, A. (2012) [1969]. "10. Favism". In Liener, I. (ed.). Toxic constituents of plant foodstuffs. Springer. pp. 293–312. ISBN 9780323147378.
  3. ^ Khazaei, Hamid (September 2019). "Eliminating vicine and convicine, the main anti-nutritional factors restricting faba bean usage". Trends in Food Science & Technology. 91: 549–556. doi:10.1016/j.tifs.2019.07.051.