Journal of the American Chemical Society, volume 138, issue 13, pages 4626-4633
Environmentally Benign CO2-Based Copolymers: Degradable Polycarbonates Derived from Dihydroxybutyric Acid and Their Platinum–Polymer Conjugates
1
Department of Chemistry, Texas A&M University, College station, Texas 77843, United States
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Publication type: Journal Article
Publication date: 2016-03-22
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
(S)-3,4-Dihydroxybutyric acid ((S)-3,4-DHBA), an endogenous straight chain fatty acid, is a normal human urinary metabolite and can be obtained as a valuable chiral biomass for synthesizing statin-class drugs. Hence, its epoxide derivatives should serve as promising monomers for producing biocompatible polymers via alternating copolymerization with carbon dioxide. In this report, we demonstrate the production of poly(tert-butyl 3,4-dihydroxybutanoate carbonate) from racemic-tert-butyl 3,4-epoxybutanoate (rac-(t)Bu 3,4-EB) and CO2 using bifunctional cobalt(III) salen catalysts. The copolymer exhibited greater than 99% carbonate linkages, 100% head-to-tail regioselectivity, and a glass-transition temperature (Tg) of 37 °C. By way of comparison, the similarly derived polycarbonate from the sterically less congested monomer, methyl 3,4-epoxybutanoate, displayed 91.8% head-to-tail content and a lower Tg of 18 °C. The tert-butyl protecting group of the pendant carboxylate group was removed using trifluoroacetic acid to afford poly(3,4-dihydroxybutyric acid carbonate). Depolymerization of poly(tert-butyl 3,4-dihydroxybutanoate carbonate) in the presence of strong base results in a stepwise unzipping of the polymer chain to yield the corresponding cyclic carbonate. Furthermore, the full degradation of the acetyl-capped poly(potassium 3,4-dihydroxybutyrate carbonate) resulted in formation of the biomasses, β-hydroxy-γ-butyrolacetone and 3,4-dihydroxybutyrate, in water (pH = 8) at 37 °C. In addition, water-soluble platinum-polymer conjugates were synthesized with platinum loading of 21.3-29.5%, suggesting poly(3,4-dihydroxybutyric acid carbonate) and related derivatives may serve as platinum drug delivery carriers.
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Tsai F. T., Wang Y., Darensbourg D. J. Environmentally Benign CO2-Based Copolymers: Degradable Polycarbonates Derived from Dihydroxybutyric Acid and Their Platinum–Polymer Conjugates // Journal of the American Chemical Society. 2016. Vol. 138. No. 13. pp. 4626-4633.
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Tsai F. T., Wang Y., Darensbourg D. J. Environmentally Benign CO2-Based Copolymers: Degradable Polycarbonates Derived from Dihydroxybutyric Acid and Their Platinum–Polymer Conjugates // Journal of the American Chemical Society. 2016. Vol. 138. No. 13. pp. 4626-4633.
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TY - JOUR
DO - 10.1021/jacs.6b01327
UR - https://doi.org/10.1021/jacs.6b01327
TI - Environmentally Benign CO2-Based Copolymers: Degradable Polycarbonates Derived from Dihydroxybutyric Acid and Their Platinum–Polymer Conjugates
T2 - Journal of the American Chemical Society
AU - Tsai, Fu Te
AU - Wang, Yanyan
AU - Darensbourg, Donald J.
PY - 2016
DA - 2016/03/22 00:00:00
PB - American Chemical Society (ACS)
SP - 4626-4633
IS - 13
VL - 138
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2016_Tsai,
author = {Fu Te Tsai and Yanyan Wang and Donald J. Darensbourg},
title = {Environmentally Benign CO2-Based Copolymers: Degradable Polycarbonates Derived from Dihydroxybutyric Acid and Their Platinum–Polymer Conjugates},
journal = {Journal of the American Chemical Society},
year = {2016},
volume = {138},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/jacs.6b01327},
number = {13},
pages = {4626--4633},
doi = {10.1021/jacs.6b01327}
}
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Tsai, Fu Te, et al. “Environmentally Benign CO2-Based Copolymers: Degradable Polycarbonates Derived from Dihydroxybutyric Acid and Their Platinum–Polymer Conjugates.” Journal of the American Chemical Society, vol. 138, no. 13, Mar. 2016, pp. 4626-4633. https://doi.org/10.1021/jacs.6b01327.