3130-92-5Relevant articles and documents
Simultaneous enzymatic synthesis of (S)-3-fluoroalanine and (R)-3-fluorolactic acid
Goncalves,Antunes,Pinto,Oestreicher
, p. 1465 - 1468 (2000)
A coupled enzymatic system for the simultaneous synthesis of (S)-3-fluoroalanine (1a) and (R)-3-fluorolactic acid (3) with L-alanine dehydrogenase (L-AlaDH) from Bacillus subtilis and rabbit muscle L-lactate dehydrogenase (L-LDH) using rac-1 and NAD+ is described. Analysis of isolated products of the laboratory preparative scale process revealed 1a in 60% yield and 88% ee and 3 in 80% yield and over 99% ee. The compounds 1a and 3 represent chiral building blocks for the synthesis of several products with pharmacological activity. Copyright (C) 2000 Elsevier Science Ltd.
Kinetic aspects involved in the simultaneous enzymatic synthesis of (S)-3-fluoroalanine and (R)-3-fluorolactic acid
Gon?alves, Luciana P.B.,Antunes, Octavio A.C.,Pinto, Gerson F.,Oestreicher, Enrique G.
, p. 219 - 227 (2007/10/03)
Desaminative oxidation of rac -3-fluoroalanine (rac-1) catalyzed by l-alanine dehydrogenase (l-ALADH) was studied by means of initial rate experiments both in the presence and in the absence of a product. Estimates of kinetic parameters of the reaction were obtained. The reaction mechanism is the sequential ordered BiTer mechanism with inhibition by excess of (S)-3-fluoroalanine. This kinetic study was the basis for the development of a couple enzymatic system for the simultaneous synthesis of (S)-3-fluoroalanine (1a) and (R)-3-fluorolactic acid (3) with l-ALADH and l-lactate dehydrogenase using rac-1 and NAD+. Analysis of isolated products revealed 1a in 60% yield and 86% ee and 3 in 80% yield and over 99% ee. Compounds 1a and 3 represent chiral building blocks for the synthesis of several products with pharmacological activity. The presence of the fluorine atom in the substrate causes a better interaction of it in the active site of the enzyme.
