Vicine

Vicine
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
CAS Number	152-93-2^N
ChemSpider	82575^Y
Jmol interactive 3D	Image
PubChem	91446
InChI 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^Y Key: KGNGTSCIQCLKEH-SYCVNHKBSA-N^Y 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
SMILES 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
Chemical formula	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 is ^YN ?)
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

↑ 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
↑ Aaron Bendich & Grace C. Clements (1953) "A revision to the structural formation of vicine and its pyrimidine aglucone, divicine", Biochimica et Biophysica Acta
↑ E. G. Brown & F. M. Roberts (1972) "Formation of Vicine and Covicine by Vicia Faba", Phytochemistry 11:3203–6

External links

Cornell U. page on vicine

Glycosides

Bond	O-glycosidic bond N-glycosidic bond S-glycosidic bond C-glycosidic bond

Geometry	α-Glycoside β-Glycoside 1,4-Glycoside 1,6-Glycoside

Glycone	Fructoside Galactoside Glucoside Glucuronide Rhamnoside Riboside

Aglycone	Alcoholic glycoside Cardiac glycoside Bufadienolide Cardenolide Cyanogenic glycoside Glycosylamine Phenolic glycoside Anthraquinone glycoside Coumarin glycoside Flavonoid glycoside Saponin Steviol glycoside Thioglycoside

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