Kinetics and Mechanism of syn-Elimination of Ammonia from (2S,3R)-3-Methylaspartic Acid by Methylaspartase

DOI: 10.1039/c39930000140

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 140 - 142 (1993)

Update date:2022-07-30

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Authors:

Archer, Catherine H.

Gani, David

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Article abstract of DOI:10.1039/c39930000140

Methylaspartase catalyses the slow syn-elimination of ammonia from the (2S,3R)--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.

Full text of DOI:10.1039/c39930000140

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Product name:(2S,3R)-N-benzyloxycarbonyl-3-methylaspartic acid dimethyl ester

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