A versatile and selective chemo-enzymatic synthesis of β-protected aspartic and γ-protected glutamic acid derivatives

Nuijens, T., Kruijtzer, J.A.W., Cusan, C., Rijkers, D.T.S., Liskamp, R.M.J. and 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, 50(23), pp. 2719-2721. (doi: 10.1016/j.tetlet.2009.03.130)

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%.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Liskamp, Professor Robert
• Authors: Nuijens, T., Kruijtzer, J.A.W., Cusan, C., Rijkers, D.T.S., Liskamp, R.M.J., and Quaedflieg, P.J.L.M.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Tetrahedron Letters
• Publisher: Elsevier
• ISSN: 0040-4039