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Periodic Incorporation of Pendant Hydroxyl Groups in Repeating Sequence PLGA Copolymers
Author(s) -
Stayshich Ryan M.,
Weiss Ryan M.,
Li Jian,
Meyer Tara Y.
Publication year - 2011
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.201000608
Subject(s) - copolymer , glycolic acid , hydrogenolysis , monomer , polymer chemistry , sequence (biology) , ether , polyester , chemistry , plga , polymer , materials science , catalysis , lactic acid , organic chemistry , biochemistry , biology , bacteria , in vitro , genetics
A series of repeating sequence poly(lactic‐ co ‐glycolic acid) copolymers (RSC PLGAs) has been prepared with the precise incorporation of a pendant benzyl‐ether substituted monomer derived from serine. Copolymers were synthesized from the assembly of sequence‐specific, stereopure dimeric, and trimeric segmers of lactic, glycolic, and ( S )‐3‐benzyloxy‐2‐hydroxypropionic acids with controlled and varied tacticities. Deprotection of the hydroxyl groups was accomplished by catalytic hydrogenolysis to yield highly functionialized, hydrophilic polyesters. The 1 H and 13 C NMR spectra for all of the copolymers were consistent with sequence and stereochemical retention and lacked the signal broadening that is inherent with more random copolymers.