KINETICS AND MECHANISM OF SYN-ELIMINATION OF AMMONIA FROM (2S,3R)-3-METHYLASPARTIC ACID BY METHYLASPARTASE

C H  ARCHER; D  GANI; Catherine Helen Botting

KINETICS AND MECHANISM OF SYN-ELIMINATION OF AMMONIA FROM (2S,3R)-3-METHYLASPARTIC ACID BY METHYLASPARTASE

C H ARCHER, D GANI, Catherine Helen Botting

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	140-142
Number of pages	3
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	2
Publication status	Published - 21 Jan 1993

Keywords

(2S,3S)-3-METHYLASPARTIC ACID

Cite this

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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.",

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year = "1993",

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AU - GANI, D

AU - Botting, Catherine Helen

PY - 1993/1/21

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N2 - 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.

AB - 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.

KW - (2S,3S)-3-METHYLASPARTIC ACID

UR - https://www.scopus.com/pages/publications/37049086056

M3 - Article

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JO - Journal of the Chemical Society, Chemical Communications

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ER -

KINETICS AND MECHANISM OF SYN-ELIMINATION OF AMMONIA FROM (2S,3R)-3-METHYLASPARTIC ACID BY METHYLASPARTASE

Abstract

Keywords

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