Pairing-Enhanced Regioselectivity: Synthesis of Alternating Poly(lactic-co-glycolic acid) from Racemic Methyl-Glycolide
Poly(lactic-co-glycolic acid) (PLGA) is used in vivo for various biomedical applications. Due to its biodegradability and biocompatibility, PLGA is uniquely suited for controlled drug delivery with parenteral administration. Previously, we established the synthesis of isotactic, alternating PLGA fr...
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Published in | Journal of the American Chemical Society Vol. 145; no. 41; pp. 22425 - 22432 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
American Chemical Society
18.10.2023
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Online Access | Get full text |
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Summary: | Poly(lactic-co-glycolic acid) (PLGA) is used in vivo for various biomedical applications. Due to its biodegradability and biocompatibility, PLGA is uniquely suited for controlled drug delivery with parenteral administration. Previously, we established the synthesis of isotactic, alternating PLGA from enantiopure starting materials. Here, to fill in the gap of the current field, we have developed the synthesis of syndioenriched, alternating PLGA from racemic methyl-glycolide (rac-MeG). The synthesis of alternating PLGA is accomplished by a highly regioselective ring-opening polymerization of rac-MeG with an optimized racemic aluminum catalyst. Mechanistic studies are carried out to elucidate the pairing-enhanced catalyst regio- and stereocontrol. Polymer sequence fidelity has been established by NMR investigations, confirming a high degree of alternation of the comonomer sequence and moderate syndiotacticity within the backbone stereoconfiguration. The resulting syndioenriched material is amorphous, which will facilitate the drug complexation behavior. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0002-7863 1520-5126 |
DOI: | 10.1021/jacs.3c05941 |