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Synthesis of a Naturally Occurring Diene‐Containing Amino Acid and Its Glutamyl Dipeptide via N ‐Acyliminium Ion Chemistry
Author(s) -
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
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200701016
Subject(s) - chemistry , dipeptide , nucleophile , amino acid , stereochemistry , pseudomonas putida , diene , methylene , organic chemistry , enzyme , biochemistry , catalysis , natural rubber
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, Germany, 2008)