Synthesis of a Naturally Occurring Diene??Containing Amino Acid and Its Glutamyl Dipeptide via N??Acyliminium Ion Chemistry

…, JH van Maarseveen, HE Schoemaker…

Index: Berkheij, Martin; Dijkink, Jan; David, Olivier R. P.; Sonke, Theo; Ijzendoorn, Denis R.; Blaauw, Richard H.; Van Maarseveen, Jan H.; Schoemaker, Hans E.; Hiemstra, Henk European Journal of Organic Chemistry, 2008 , # 5 p. 914 - 924

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Citation Number: 5

Abstract

Abstract The syntheses of the naturally occurring unusual unsaturated amino acid (S)-2- amino-3-methylene-4-pentenoic acid and the corresponding γ-glutamyl dipeptide are described. Key steps are an N-acyliminium ion addition using allenylmethylsilane as nucleophile and an enzymatic resolution mediated by the L-aminopeptidase from Pseudomonas putida.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, ...