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Synthesis and organocatalytic ring-opening polymerization of cyclic esters derived from L-malic acid
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Pounder, Ryan J. and Dove, Andrew P. (2010) Synthesis and organocatalytic ring-opening polymerization of cyclic esters derived from L-malic acid. Biomacromolecules, Vol.11 (No.8). pp. 1930-1939. doi:10.1021/bm1004355 ISSN 1525-7797.
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Official URL: http://dx.doi.org/10.1021/bm1004355
Abstract
The synthesis of 3-(S)-[(benzyloxycarbonyl)methyl]-1,4-dioxane-2,5-dione (BMD) and 3,6-(S)-[di(benzyloxycarbonyl)methyl]-1,4-dioxane-2,5-dione (malide) from commercially available L-malic acid is reported. Ring-opening polymerization (ROP) studies of BMD are reported showing that the controlled ROP of this monomer is possible in the absence of transesterification side reactions, despite the presence of side-chain esters, using 1-(3,5-bis(trifluoromethyl)phenyl)-3-cyclohexylthiourea and (-)-sparteine to catalyze the polymerization. The ROP of malide with this system was ineffective. Investigation of the effect of initiating species revealed that the electronic nature of the alcohol had a greater effect on the ultimate molecular weight and hence initiator efficiency than steric considerations. Deprotection of the resultant poly(BMD) using H-2 and Pd/C resulted in hydrophilic poly(glycolic-co-malic acid)s (PGMAs) that were able to undergo autocatalytic degradation in dilute H2O solution such that complete degradation was observed within 6 days.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Library of Congress Subject Headings (LCSH): | Ring-opening polymerization, Polymers -- Biodegradation, Aliphatic compounds, Polyesters, Copolymers, Malic acid | ||||
Journal or Publication Title: | Biomacromolecules | ||||
Publisher: | American Chemical Society | ||||
ISSN: | 1525-7797 | ||||
Official Date: | 9 August 2010 | ||||
Dates: |
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Volume: | Vol.11 | ||||
Number: | No.8 | ||||
Number of Pages: | 10 | ||||
Page Range: | pp. 1930-1939 | ||||
DOI: | 10.1021/bm1004355 | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published | ||||
Access rights to Published version: | Restricted or Subscription Access | ||||
Funder: | Research Councils UK (RCUK), Engineering and Physical Sciences Research Council (EPSRC), Advantage West Midlands (AWM), European Regional Development Fund (ERDF) | ||||
Grant number: | EP/C007999/1 (EPSRC) |
Data sourced from Thomson Reuters' Web of Knowledge
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