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

Judith Hoffmann; Uli Kazmaier

doi:10.1055/s-0034-1378908

Synthesis, Table of Contents

Synthesis 2015; 47(03): 411-420
DOI: 10.1055/s-0034-1378908

paper

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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Abstract

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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).

Key words

amino acids - metathesis - peptides - photochemistry - photocleavage - protecting groups

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References

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