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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Wiesendanger, R., Martinoni, B., Boller, T. et al. Biosynthesis of 1-aminocyclopropanecarboxylic acid: Steric course of the reaction at the C-4 position. Experientia 42, 207–209 (1986). https://doi.org/10.1007/BF01952472
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DOI: https://doi.org/10.1007/BF01952472