Synthesis 2015; 47(03): 411-420
DOI: 10.1055/s-0034-1378908
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Cyclic Peptides through Ring-Closing Metathesis of Photolabile Protecting Groups

Judith Hoffmann
Universitaet des Saarlandes, Institut für Organische Chemie, 66123 Saarbruecken, Germany   Fax: +49(681)3022409   eMail: u.kazmaier@mx.uni-saarland.de
,
Uli Kazmaier*
Universitaet des Saarlandes, Institut für Organische Chemie, 66123 Saarbruecken, Germany   Fax: +49(681)3022409   eMail: u.kazmaier@mx.uni-saarland.de
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Publikationsverlauf

Received: 20. August 2014

Accepted after revision: 07. Oktober 2014

Publikationsdatum:
12. November 2014 (online)


Abstract

The new photolabile protecting groups 4-allyl-5-methoxy-3-nitrobenzyl (AMNB) and 4-allyl-5-methoxy-3-nitrobenzyloxycarbonyl (AMNBOC) with an allylic side chain can easily be obtained from vanillin. These protecting groups can be introduced on the C- as well as on the N-terminus of peptides, and subsequent ring-closing metatheses provides a straightforward protocol for the synthesis of cyclic peptides. The protecting groups can be removed under UVA irradiation (365 nm).

Supporting Information