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Divicine

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Divicine
pyrimidine tautomer
pyrimidinone tautomer

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IUPAC name
2,6-diamino-4,5-dihydroxypyrimidine
Other names
2,6-diamino-4,5-pyrimidinediol; 2,6-diamine-5-hydroxy-4(3H)-pyrimidinone; 2,4-diamino-5,6-dihydroxypyrimidine
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32267-39-3 [1] 7pxY ChemSpider 2971290 7pxY Jmol-3D images Image

(pyrimidine tautomer)
Image (pyrimidinone tautomer)

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C4H6N4O2 Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1 Appearance Brownish needles Soluble in 10% KOH
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Divicine (2,6-diamino-4,5-dihydroxypyrimidine) is an oxidant and a base with alkaloidal properties found in fava beans and Lathyrus sativus. It is an aglycone of vicine. A common derivative is the diacetate form (2,6-diamino-1,6-dihydro-4,5-pyrimidinedione).[2]

Occurrence

Divicine is found in fava beans and in the legume Lathyrus sativus, also known as khesari, which is a cheap and robust food source commonly grown in Asia and East Africa.

Synthesis

In plants, reduced divicine is formed from the hydrolysis of the inactive β–glucoside, vicine.[3]

A simplified three-step process for artificial divicine synthesis: (1) The benzyl group of 2-amino-5-benzyloxy-4-hydroxypyrimidine is removed by acid hydrolysis, yielding 2-amino-4,5-dihydroxypyrimidine. (2) This intermediate is then treated with nitrous acid to yield the slightly soluble orange product, 2-amino-6-nitrosopyrimidine-4,5-diol (3) which is then reduced with sodium dithionite to yield divicine.[4]

Toxicity

Divicine has been deemed a hemotoxic component of fava beans and plays a role in the development of favism, a disorder that involves a hemolytic response to the consumption of broad beans due to glucose-6-phosphate dehydrogenase (G6PD or G6PDH) deficiency. This deficiency, an X-linked recessive hereditary disease, is the most common enzyme deficiency worldwide. It is particularly common in those of African, Asian, Mediterranean, and Middle-Eastern descent. Symptoms of favism include hemolysis, prolonged jaundice, kernicterus, and even acute renal failure in extreme cases.[5]

The specific mechanism of divicine’s toxicity is still unknown. It had been established that the β–glucosides vicine and convicine were linked to the precipitation of hemolytic crises in G6PDH-deficient individuals,[6] but in a more recent study of rat erythrocyte toxicity, exposure to 1.5 mM of divicine dramatically reduced survival rates while exposure to 5 mM of vicine did not. These results suggest that divicine is a direct-acting hemolytic agent and likely the direct cause of favism.[7]

Divicine is also present in and at least partially responsible for the poisonous action of Lathyrus sativus - a legume commonly grown in drought- and famine-prone regions of Asia and East Africa as an ‘insurance crop’ for human consumption and livestock feed when other crops fail to grow, despite their known health hazards.[8]

References

  1. ^ http://www.druglead.com/cds/divicine.html
  2. ^ Bendich, C. (1953). Biochim. Biophys. 12: 462.  Missing or empty |title= (help)
  3. ^ Baker, M.; Bosia, A. (1984). "Mechanism of Action of Divicine in a Cell-free System and in Glucose-6-phosphate Dehydrogenase-deficient Red Cells". Toxicol. Pathol. 12: 331–336. doi:10.1177/019262338401200405. 
  4. ^ Chesterfield, J. et al. (1964). "194. Pyrimidines. Part XIII. Electrophilic substitution at position 6 and a synthesis of divicine (2,4-diamino-5,6-dihydroxypyrimidine)". J. Chem. Soc.: 1001–1005. 
  5. ^ Frank, J. (2005). "Diagnosis and management of G6PD deficiency". Am. Fam. Phys. 72: 1277–1282. 
  6. ^ Doyle, M. Ellin (1995). Food Safety 1995. Marcel Dekker, Inc. p. 357. ISBN 0-8247-9624-1. 
  7. ^ McMillan, D. et al. (2001). "Favism: Effect of Divicine on Rat Erythrocyte Sulfhydryl Status, Hexose Monophosphate Shunt Activity, Morphology, and Membrane Skeletal Proteins". Toxicol. Sci. 62: 353–359. PMID 11452148. doi:10.1093/toxsci/62.2.353. 
  8. ^ http://www.biology-online.org/dictionary/Divicine