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Synthesis of poly-O-tert-butyl-L-serine and poly-L-serine

✍ Scribed by Nancy M. Tooney; Gerald D. Fasman

Publisher: Wiley (John Wiley & Sons)
Year: 1968
Tongue: English
Weight: 816 KB
Volume: 6
Category: Article
ISSN: 0006-3525
DOI: 10.1002/bip.1968.360060107

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✦ Synopsis

Synopsis

The synthesis of polymers containing 0-tert-butyl-L-serine, 0-tert-butyl-DL-serine, L-serine, and DL-serine is reported. The N-benzyloxycarbonyl-(L or DL)-serine benzyl ester was used to synthesize the corresponding N-benzyloxycarbonyl-0-tert-butyl-(L or DL)-serine benzyl ester. Catalytic hydrogenation of this material gave 0 -f e dbutyl-(L or DL)-serine. The reaction of 0-tert-butyl-(L or DL)-serine with phosgene produced the corresponding N-carboxyanhydrides. The kinetics of polymerization of N-carboxyanhydrides were investigated to facilitate the preparation of block copolymers. The 0-tert-butyl blocking group was removed from polymers by treatment with HCl and YBr in benzene. Both high molecular weight (water-insoluble) and low molecular weight (water-soluble) homopolymers have been prepared, as well as watersoluble block copolymers of the type (DL-serine), (L-serine), (DL-serine),.

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