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Synthesis of Block Copolypeptides by Click Chemistry

✍ Scribed by Willy Agut; Reda Agnaou; Sébastien Lecommandoux; Daniel Taton

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
264 KB
Volume
29
Category
Article
ISSN
1022-1336

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✦ Synopsis

Abstract

A novel synthetic methodology to diblock copolypeptides was developed by ring‐opening polymerization (ROP) of N‐carboxyanhydrides (NCAs) from α‐ω‐functionalized initiators combined with the Huisgen 1,3 dipolar cycloaddition (click chemistry). Poly(γ‐benzyl‐L‐glutamate) (PBLGlu) and poly(trifluoroacetyl‐L‐Lysine) (PTFALys) containing either an azide or an alkyne functional group in α‐position were first synthesized by ROP of the corresponding NCA at room temperature in DMF as a solvent, using appropriate ω‐amino‐containing α‐alkyne and α‐azido difunctional initiators. The copper(I)‐catalyzed coupling reactions of α‐azido‐PBLGlu with the α‐alkyne‐PTFALys, on the one hand, and of the α‐alkyne‐PBLGlu with the α‐azido‐PTFALys, on the other hand were suitably accomplished in DMF. This afforded the targeted PBLGlu‐b‐PTFALys diblock copolypeptides possessing a triazole group in between the two blocks, as evidenced by SEC, IR, and NMR analysis. Block copolypeptides could be successfully purified by selective extraction with chloroform.

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