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

✍ Scribed by Timo Nuijens; John A.W. Kruijtzer; Claudia Cusan; Dirk T.S. Rijkers; Rob M.J. Liskamp; Peter J.L.M. Quaedflieg

Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 252 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.03.130

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✦ Synopsis

Two versatile, high yielding, and efficient chemo-enzymatic methods for the synthesis of b-protected Asp and c-protected Glu derivatives using Alcalase are described. The first method is based on the a-selective enzymatic hydrolysis of symmetrical aspartyl and glutamyl diesters. The second method involving mixed diesters comprises a three-step protocol using (i) a-selective enzymatic methyl-esterification, (ii) chemical b-esterification, and finally (iii) a-selective enzymatic methyl ester hydrolysis. The yields of the purified b-and c-esters range from 77% to 91%.

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