S)-Diethyl malate 1a was prepared (70-80% yield; > 98% optical purity) by an enantioselective reduction of sodium diethyl oxalacetate 2 by fermenting baker's yeast (Saccharomyces cerevisiae). Other microorganisms were tested for their capability of reducing 2. Most of them afforded (S)-1a-with ee from 8 to 94% and only Candida utilis, Aspergillus niger and Lactobacillus fermentum ILC G18D preferentially reduced compound 2 to (R)-1a. (R)-Dimethyl malate 1b was obtained from (R,S)-malate 1b by hydrolysis with pig liver esterase (PLE), the highest ee (93%) being realized at 0-degrees-C in 20% aqueous methanol. Enzymatic hydrolyses of protected malates 1d and 1e did not lead to improvement of the ee.

A biocatalytic approach to the enantioselective synthesis of (R)- and (S)-malic acid / E. Santaniello, P. Ferraboschi, P. Grisenti, F. Aragozzini, E. Maconi. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - :3(1991), pp. 601-605.

A biocatalytic approach to the enantioselective synthesis of (R)- and (S)-malic acid

E. Santaniello
Primo
;
P. Ferraboschi
Secondo
;
1991

Abstract

S)-Diethyl malate 1a was prepared (70-80% yield; > 98% optical purity) by an enantioselective reduction of sodium diethyl oxalacetate 2 by fermenting baker's yeast (Saccharomyces cerevisiae). Other microorganisms were tested for their capability of reducing 2. Most of them afforded (S)-1a-with ee from 8 to 94% and only Candida utilis, Aspergillus niger and Lactobacillus fermentum ILC G18D preferentially reduced compound 2 to (R)-1a. (R)-Dimethyl malate 1b was obtained from (R,S)-malate 1b by hydrolysis with pig liver esterase (PLE), the highest ee (93%) being realized at 0-degrees-C in 20% aqueous methanol. Enzymatic hydrolyses of protected malates 1d and 1e did not lead to improvement of the ee.
stereochemical control; bakers-yeast; asymmetric-synthesis; carbonyl-compounds; L-carnitine; esters; reduction; derivatives; hydroxy; 3-OXO
Settore BIO/10 - Biochimica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/182436
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