Synthesis and Diversification of Pyridone Dipeptide Chromophores

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.

Key words

amino acids - fused-rings - pyridones - thiazolidine lactams - cross-coupling

References

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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: [phone]; E-mail: [e-mail].

11

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