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

Berkheij Martin | Zendy; Dijkink Jan | Zendy; David Olivier R. P. | Zendy; Sonke Theo | Zendy; IJzendoorn Denis R. | Zendy; Blaauw Richard H. | Zendy; van Maarseveen Jan H. | Zendy; Schoemaker Hans E. | Zendy; Hiemstra Henk | Zendy

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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)

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