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Synthesis of Block Copolypeptides by Click Chemistry
Author(s) -
Agut Willy,
Agnaou Reda,
Lecommandoux Sébastien,
Taton Daniel
Publication year - 2008
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.200800123
Subject(s) - click chemistry , cycloaddition , alkyne , chemistry , azide , polymer chemistry , 1,3 dipolar cycloaddition , polymerization , triazole , combinatorial chemistry , organic chemistry , catalysis , polymer
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.