NDLI: Optimization of N-carboxyanhydride (NCA) polymerization by variation of reaction temperature and pressure

Content Provider	Royal Society of Chemistry (RSC)
Author	Heise, Andreas Wilsens, Karel H. R. M. Habraken, Gijs J. M. Koning, Cor E.
Copyright Year	2011
Abstract	Several new methods for the controlled ring-opening polymerization of N-carboxyanhydrides (NCA ROP) have been established in the recent past, all of which based on the normal amine mechanism. In this paper the optimal NAM polymerization conditions were investigated combining the high-vacuum and the low-temperature for the NCAs of γ-benzyl-L-glutamate (BLG), Nε-benzyloxycarbonyl-L-lysine (ZLL), L-alanine (Ala), β-benzyl-L-aspartate (BLA), O-benzyl-L-serine (BLS), and O-benzyl-L-threonine (BLT). The polymerizations were followed by FTIR, size exclusion chromatography (SEC) and MALDI-ToF-MS to provide information of the monomer conversion, polymer molecular weight and chain composition as a function of pressure and temperature. It was found that the studied NCAs could be divided into two groups: in the first group monomers of BLG, ZLL and Ala polymerized considerably faster when a lower pressure of 1 × 10−5 bar was applied. MALDI-ToF-MS analysis confirmed that the formation of side products for these monomers mostly started after full monomer conversion. The second group of monomers, i.e. BLA, BLS and BLT, polymerized considerably slower than the first group and no effect was observed from the lower pressure. On the other hand, the number of side reactions was significant at 20 °C, so that the polymerizations for the latter monomers should preferably be done at 0 °C. By combining both methods, multiblock polypeptides were synthesized including a tetrablock of PBLG-b-PAla-b-PZLL-b-PBLA with a polydispersity of 1.3.
Starting Page	1322
Ending Page	1330
Page Count	9
File Format	HTM / HTML PDF
ISSN	17599954
Volume Number	2
Issue Number	6
Journal	Polymer Chemistry
DOI	10.1039/c1py00079a
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Dispersity Alanine BLS Ring-opening polymerization Polymer Amino acid N-carboxyanhydride SEC lysine BLA Living polymerization Ala Size-exclusion chromatography U.S. Securities and Exchange Commission Monomer
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Bioengineering Biomedical Engineering Polymers and Plastics

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