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Synthesis of poly‐ O ‐ tert ‐butyl‐ L ‐serine and poly‐ L ‐serine
Author(s) -
Tooney Nancy M.,
Fasman Gerald D.
Publication year - 1968
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.1968.360060107
Subject(s) - serine , chemistry , phosgene , polymerization , catalysis , copolymer , polymer , polymer chemistry , organic chemistry , enzyme
The synthesis of polymers containing O‐tert ‐butyl‐ L ‐serine, O‐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‐ O‐tert ‐butyl‐( L or DL )‐serine benzyl ester. Catalytic hydrogenation of this material gave O‐tert ‐butyl‐( L or DL )‐serine. The reaction of O‐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 O‐tert ‐butyl blocking group was removed from polymers by treatment with HCl and HBr in benzene. Both high molecular weight (water‐insoluble) and low molecular weight (water‐soluble) homopolymers have been prepared, as well as water‐soluble block copolymers of the type ( DL ‐serine) x ( L ‐serine) y , ( DL ‐serine) z .