Sequence control of poly(lactic-co-glycolic acid) (PLGA) is an effective technique for tuning its degradation properties for various biomedical applications. We herein report the synthesis of alternating PLGA via a regioselective ring-opening polymerization of (S)-methyl glycolide. An enantiopure aluminum salen catalyst with binaphthyl backbone facilitates the regioselective ring-opening of this unsymmetrical cyclic diester exclusively at the glycolide acyl−oxygen bond site. A dual steric and chirality control accounts for the high regioselectivity. This living, chain-growth polymerization is able to reach low dispersities with tailored molecular weights. Quantitative regioselectivity calculations and sequence error analysis, based on NMR studies, have been established for this sequence-controlled polymer.

Chirality-directed regioselectivity: An approach for the synthesis of alternating poly(Lactic-co-glycolic acid)

ACS Spring 2022

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