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Synthesis of linear and cyclic peptides related to Met- and Leu-enkephalin

✍ Scribed by J. W. van Nispen; H. M. Greven

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 897 KB
Volume: 101
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19821011206

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✦ Synopsis

Abstract

The synthesis is described of several peptides containing the sequence Phe‐Met. In order to limit enzymatic degradation and to restrict the number of possible conformations they were cyclized with variable ring size. Some unexpected side‐reactions were encountered during the synthesis of the linear precursors: partial cleavage of the active ester during removal of the Bocprotecting group, partial cleavage of the Gly‐Gly peptide bond during hydrazinolysis of an ester function and failure to obtain the p‐nitrophenyl ester of Boc‐Phe‐Met‐Gly‐Gly‐OH via the DCC method. Diphenyl phosphoroazidate was finally used for the cyclization of several linear peptides. Some results of behavioural activity and metabolic stability are mentioned.

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