101. Synthesis of block copolypeptides by click chemistry
- Author
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AGUT, Willy, AGNAOU, Reda, LECOMMANDOUX, Sebastien, TATON, Daniel, Laboratoire de Chimie des polymères organiques (LCPO), Centre National de la Recherche Scientifique (CNRS)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Université Sciences et Technologies - Bordeaux 1-Institut de Chimie du CNRS (INC), Team 3 LCPO : Polymer Self-Assembly & Life Sciences, Laboratoire de Chimie des Polymères Organiques (LCPO), Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC), and Team 1 LCPO : Polymerization Catalyses & Engineering
- Subjects
L-LEUCINE ,DIBLOCK COPOLYMERS ,[CHIM.POLY]Chemical Sciences/Polymers ,L-LYSINE ,MODULAR SYNTHESIS ,TRIBLOCK COPOLYMERS ,L-GLUTAMIC ACID ,MATERIALS SCIENCE ,POLYPEPTIDE ,ONE-POT SYNTHESIS ,ROD-COIL - Abstract
International audience; A novel synthetic methodology to diblock copolypeptides was developed by ring-opening polymerization (ROP) of N-carboxyanhydrides (NCAs) from alpha-omega-functionalized initiators combined with the Huisgen 1,3 dipolar cycloaddition (click chemistry). Poly(gamma-benzyl-L-glutamate) (PBLGlu) and poly(trifluoroacetyl-L-Lysine) (PTFALys) containing either an azide or an alkyne functional group in alpha-position were first synthesized by ROP of the corresponding NCA at room temperature in DMF as a solvent, using appropriate omega-amino-containing alpha-alkyne and a-azido difunctional initiators. The Copper(I) -catalyzed coupling reactions of alpha-azido-PBLGlu with the alpha-alkyne-PTFALys, on the one hand, and of the alpha-alkyne-PBLGlu with the alpha-azido-PTFALys, on the other hand were suitably accomplished in DMF. This afforded the targeted PBLGlu-b-PTFALys diblock copolypeptides pos- sessing a triazole group in between the two 1 blocks, as evidenced by SEC, IR, and NMR analysis. Block copolypeptides could be successfully purified by selective extraction with chloroform.
- Published
- 2008