Kinetics and mechanism of syn-elimination of ammonia from (2S,3R)-3-methylaspartic acid by methylaspartase
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 2,p. 140-142
- https://doi.org/10.1039/c39930000140
Abstract
Methylaspartase catalyses the slow syn-elimination of ammonia from the (2S,3R)-[L-erythro]-diastereoisomer of the natural substrate (2S,3S)-3-methylaspartic acid, to give mesaconic acid; the reaction does not involve C-3 epimerisation followed by normal anti-elimination, ruling-out the possibility of a carbanion intermediate, but, displays large primary deuterium isotope effects consistent with concerted C–H and C–N bond cleavage.Keywords
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