Decarboxylation of (S)-glutamic acid (1) in 2H2O, catalysed by glutamate decarboxylase from Escherichia coli (E.C.4.1.1.15), afforded 4-[4-2H]aminobutyric acid (2b). (+)-(S)-4-[4- 2H]aminobutyric acid (2c) was synthesized and the 1H n.m.r. spectrum of the (1S,4R)-O-camphanoylamide of its methyl ester compared with the same derivative of (2b) in the presence of the shift reagent [Eu(dpm)3]. It was shown that (2b) is in the (R) configuration and that glutamate decarboxylase catalyses the decarboxylation of (1) with retention of configuration.

Stereochemical course of the decarboxylation of (S)-glutamic acid by glutamate decarboxylase from Escherichia coli (E.C. 4.1.1.15) / E. Santaniello, M. G. Kienle, A. Manzocchi, E. Bosisio. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 7(1979), pp. 1677-1679.

Stereochemical course of the decarboxylation of (S)-glutamic acid by glutamate decarboxylase from Escherichia coli (E.C. 4.1.1.15)

E. Santaniello
Primo
;
A. Manzocchi
Penultimo
;
E. Bosisio
Ultimo
1979

Abstract

Decarboxylation of (S)-glutamic acid (1) in 2H2O, catalysed by glutamate decarboxylase from Escherichia coli (E.C.4.1.1.15), afforded 4-[4-2H]aminobutyric acid (2b). (+)-(S)-4-[4- 2H]aminobutyric acid (2c) was synthesized and the 1H n.m.r. spectrum of the (1S,4R)-O-camphanoylamide of its methyl ester compared with the same derivative of (2b) in the presence of the shift reagent [Eu(dpm)3]. It was shown that (2b) is in the (R) configuration and that glutamate decarboxylase catalyses the decarboxylation of (1) with retention of configuration.
Stereoisomerism; Carboxy-Lyases; Glutamate Decarboxylase; Escherichia coli; Glutamates; Catalysis
Settore BIO/10 - Biochimica
Settore BIO/14 - Farmacologia
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/196601
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