Hypoglycin

From Wikipedia, the free encyclopedia

Hypoglycin
IUPAC name	L(S)-2-amino-3-(2-methylidenecyclopropyl)- propanoic acid
Other names	Hypoglycin A, Hypoglycine, 2-Methylenecyclopropanylalanine
Identifiers
CAS number	[156-56-9]
SMILES	C=C1CC1CC(C(=O)O)N
Properties
Molecular formula	C7H11NO2
Molar mass	141.17 g/mol
Melting point	282°C (555.15 K)
Boiling point	(? K)
Solubility in water	? g/100 ml (?°C)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Hypoglycin is a naturally occurring organic compound in the species Blighia sapida. It is particularly concentrated in the fruit of the plant. Hypoglycin is toxic if ingested and is the causative agent of Jamaican Vomiting Sickness. It is an amino acid and chemically related to lysine. It competitively binds to enzymes used in the catabolism of lysine and is the reason why it and its metabolite MCPA (methylene cyclopropyl acetic acid) are toxic.

The metabolite MCPA also is a potent inhibitor of Acyl-CoA dehydrogenase, preventing the metabolism of fatty acids. The symptoms of ingestion Hypoglycin-A are intolerance to prolong fasting (due to inability to switch from glucose to fatty acid oxidation), impaired ketogensis, vomiting, lethargy, unconsciousness,coma death, and increased urinary excretion of dicarboxylic acid,due to omega oxidation that occurs in the ER.

[edit] References

This article does not cite any references or sources. (September 2007) Please help improve this article by adding citations to reliable sources. Unverifiable material may be challenged and removed.