A versatile and selective chemo-enzymatic synthesis of β-protected aspartic and γ-protected glutamic acid derivatives
Publication date
2009-06-10
Authors
Nuijens, T.
Kruijtzer, John
Cusan, Claudia
Rijkers, D.T.S.
Liskamp, Rob M.J.
Quaedflieg, Peter J.L.M.
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Document Type
Article
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Abstract
Two versatile, high yielding, and efficient chemo-enzymatic methods for the synthesis of β-protected Asp and γ-protected Glu derivatives using Alcalase are described. The first method is based on the α-selective enzymatic hydrolysis of symmetrical aspartyl and glutamyl diesters. The second method involving mixed diesters comprises a three-step protocol using (i) α-selective enzymatic methyl-esterification, (ii) chemical β-esterification, and finally (iii) α-selective enzymatic methyl ester hydrolysis. The yields of the purified β- and γ-esters range from 77% to 91%. © 2009 Elsevier Ltd. All rights reserved.
Keywords
Amino acids, Enzymes, Esters, Hydrolysis, Protecting groups, aspartic acid, glutamic acid derivative, subtilisin, article, enzyme synthesis, esterification, hydrolysis
Citation
Nuijens, T, Kruijtzer, J A W, Cusan, C, Rijkers, D T S, Liskamp, R M J & Quaedflieg, P J L M 2009, 'A versatile and selective chemo-enzymatic synthesis of β-protected aspartic and γ-protected glutamic acid derivatives', Tetrahedron Letters, vol. 50, no. 23, pp. 2719-2721. https://doi.org/10.1016/j.tetlet.2009.03.130