Synthesis 2006(19): 3224-3230  
DOI: 10.1055/s-2006-942546
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Diversification of Pyridone Dipeptide Chromophores

Harald Seger, Armin Geyer*
Fachbereich Chemie der Philipps-Universität Marburg, 35032 Marburg, Germany
Fax: +49(6421)2822021; e-Mail: geyer@staff.uni-marburg.de;
Further Information

Publication History

Received 18 May 2006
Publication Date:
02 August 2006 (online)

Abstract

An improved synthetic protocol transforms d-alduronolactone via a bicyclic dipeptide lactam 2 into pyridone dipeptides with either Boc- or Fmoc-protecting groups 5 or 6. Regioselective bromination of 5 yields dipeptide 10 which is further diversified in Pd-catalyzed cross coupling reactions. This late diversification of a common peptide precursor makes a maximum number of rigid dipeptide chromophores accessible. The dipeptides 11, 12, and 13 exemplify a general strategy of accessing conformationally locked peptide chromophores as tools for chemical biology.

10

CCDC number 607190. Crystallographic data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk.

11

Beck-Sickinger, A.; Haack, M.; Enck, S.; Geyer, A.; Seger, H., manuscript in preparation.