Biosynthesis of 1-aminocyclopropanecarboxylic acid: Steric course of the reaction at the C-4 position |
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Authors: | R Wiesendanger B Martinoni T Boller D Arigoni |
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Institution: | (1) Present address: Laboratorium für Organische Chemie, ETH-Zentrum, CH-8092 Zürich, Switzerland;(2) Botanisches Institut, Universität Basel, CH-4056 Basel, Switzerland |
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Abstract: | Summary Under the action of the appropriate synthase from ripe tomatoes a 1 1 mixture of (3S, 4R)-3,4-2H2] and (3R, 4S)-3,4-2H2]-(2S)-adenosylmethionine is transformed into a 1 1 mixture of the two meso forms of 2H2]-1-aminocyclopropanecarboxylic acid, a result which proves the operation of an inversion mechanism and which is consistent with direct nucleophilic displacement of the leaving group in the substrate. |
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Keywords: | 1-Aminocyclopropanecarboxylic acid ACC-synthase PLP-catalyzed reaction stereochemistry |
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