Hypoglycin A
Names | |
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IUPAC name
3-[(1R-2-Methylidenecyclopropyl]-L-alanine
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Systematic IUPAC name
(2S)-2-Amino-3-[(1R)-2-methylidenecyclopropyl]propanoic acid | |
Other names
Hypoglycin A; Hypoglycine; 2-Methylenecyclopropanylalanine
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Identifiers | |
3D model (
JSmol ) |
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ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.189.936 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C7H11NO2 | |
Molar mass | 141.170 g·mol−1 |
Melting point | 282 °C (540 °F; 555 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hypoglycin A is a naturally occurring
Sources
The entirety of the unripe Ackee fruit is toxic and contains large amounts of hypoglycin. The fruit is safe to eat only when the fruit is allowed to fully open and expose the large black seeds while on the tree. The levels of the toxin decrease over time though from approximately 1000 ppm to around 0.1 ppm in the mature fruit.[4]
Relatives of Ackee, including
Toxicity
Hypoglycin A is a
The reduction in gluconeogenesis and the reduction in fatty acid oxidation are thought to be the cause of most of the symptoms of Jamaican vomiting sickness. The blocking of fatty acid metabolism causes cells to start using glycogen for energy. Once glycogen is depleted, the body is unable to produce more, which leads to severe hypoglycemia. These biochemical effects are detected by an excess of medium chain fatty acids in urine and
Synthesis
In 1958, John Carbon, William Martin, and Leo Swett were the first to synthesize hypoglycin A, in
In 1992, Jack Baldwin, Robert Adlington, David Bebbington, and Andrew Russell accomplished the first asymmetric total synthesis of the individual diastereoisomers of hypoglycin A, using the Sharpless epoxidation to permit an asymmetric methylene cyclopropane synthesis.[8][9] 1H NMR and circular dichroism studies identifies the major diastereoisomer of natural hypogycin A as (2S, 4R) and the minor diastereoisomer as (2S, 4S).
See also
References
- ^ a b "Ackee Fruit Toxicity". Medscape. 2018-06-13.
- S2CID 206002430.
- PMID 28153514.
- ^ a b "THE ACKEE FRUIT (BLIGHIA SAPIDA) AND ITS ASSOCIATED TOXIC EFFECTS". University of British Columbia. 2005-11-17.
- PMID 25897979
- TOXNET.
- ISSN 0022-4936.
- ISSN 0040-4020.