Tandem dynamic kinetic resolution and enzymatic polycondensation to synthesize mPEG‐functionalized poly(amine‐co‐ester)‐type chiral prodrugs
Abstract Amphiphilic poly(amine‐co‐ester)s, which contain a single effective enantiomer of an asymmetric drug and thus can avoid potentially serious side effects, are difficult to prepare through nonselective chemical routes not only in the process of introducing chiral drugs to the polymer, but als...
Published in: | Journal of Polymer Science Part A: Polymer Chemistry |
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crwiley:10.1002/pola.26594 2024-06-02T07:58:39+00:00 Tandem dynamic kinetic resolution and enzymatic polycondensation to synthesize mPEG‐functionalized poly(amine‐co‐ester)‐type chiral prodrugs Qian, Xueqi Jiang, Zhengyang Lin, Xianfu Wu, Qi 2013 http://dx.doi.org/10.1002/pola.26594 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fpola.26594 https://onlinelibrary.wiley.com/doi/pdf/10.1002/pola.26594 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Journal of Polymer Science Part A: Polymer Chemistry volume 51, issue 9, page 2049-2057 ISSN 0887-624X 1099-0518 journal-article 2013 crwiley https://doi.org/10.1002/pola.26594 2024-05-03T10:51:17Z Abstract Amphiphilic poly(amine‐co‐ester)s, which contain a single effective enantiomer of an asymmetric drug and thus can avoid potentially serious side effects, are difficult to prepare through nonselective chemical routes not only in the process of introducing chiral drugs to the polymer, but also in the synthesis of the polymer's backbone by metal catalysts. A model of racemic mexiletine, an important antiarrhythmic agent, was used to demonstrate the tandem combination of Candida antarctica lipase B (CAL‐B)‐ and Pd/C‐catalyzed dynamic kinetic resolution (DKR) and subsequent CAL‐B‐catalyzed polycondensation, as an efficient protocol to prepare poly(ethylene glycol)‐functionalized poly(amine‐co‐ester)s containing (R)‐mexiletine with 99% ee value. Chemoenzymatic DKR and enzymatic polymerization conditions were optimized, and the optical purity of incorporated (R)‐mexiletine was confirmed through its hydrolysis from polyester. The copolymers can readily self‐assemble into nanometer‐scale‐sized micelles with well‐dispersed spheres, which have a size distribution that can be efficiently adjusted by changing the polymer concentration. © 2013 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013 Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Journal of Polymer Science Part A: Polymer Chemistry 51 9 2049 2057 |
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Wiley Online Library |
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Abstract Amphiphilic poly(amine‐co‐ester)s, which contain a single effective enantiomer of an asymmetric drug and thus can avoid potentially serious side effects, are difficult to prepare through nonselective chemical routes not only in the process of introducing chiral drugs to the polymer, but also in the synthesis of the polymer's backbone by metal catalysts. A model of racemic mexiletine, an important antiarrhythmic agent, was used to demonstrate the tandem combination of Candida antarctica lipase B (CAL‐B)‐ and Pd/C‐catalyzed dynamic kinetic resolution (DKR) and subsequent CAL‐B‐catalyzed polycondensation, as an efficient protocol to prepare poly(ethylene glycol)‐functionalized poly(amine‐co‐ester)s containing (R)‐mexiletine with 99% ee value. Chemoenzymatic DKR and enzymatic polymerization conditions were optimized, and the optical purity of incorporated (R)‐mexiletine was confirmed through its hydrolysis from polyester. The copolymers can readily self‐assemble into nanometer‐scale‐sized micelles with well‐dispersed spheres, which have a size distribution that can be efficiently adjusted by changing the polymer concentration. © 2013 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013 |
format |
Article in Journal/Newspaper |
author |
Qian, Xueqi Jiang, Zhengyang Lin, Xianfu Wu, Qi |
spellingShingle |
Qian, Xueqi Jiang, Zhengyang Lin, Xianfu Wu, Qi Tandem dynamic kinetic resolution and enzymatic polycondensation to synthesize mPEG‐functionalized poly(amine‐co‐ester)‐type chiral prodrugs |
author_facet |
Qian, Xueqi Jiang, Zhengyang Lin, Xianfu Wu, Qi |
author_sort |
Qian, Xueqi |
title |
Tandem dynamic kinetic resolution and enzymatic polycondensation to synthesize mPEG‐functionalized poly(amine‐co‐ester)‐type chiral prodrugs |
title_short |
Tandem dynamic kinetic resolution and enzymatic polycondensation to synthesize mPEG‐functionalized poly(amine‐co‐ester)‐type chiral prodrugs |
title_full |
Tandem dynamic kinetic resolution and enzymatic polycondensation to synthesize mPEG‐functionalized poly(amine‐co‐ester)‐type chiral prodrugs |
title_fullStr |
Tandem dynamic kinetic resolution and enzymatic polycondensation to synthesize mPEG‐functionalized poly(amine‐co‐ester)‐type chiral prodrugs |
title_full_unstemmed |
Tandem dynamic kinetic resolution and enzymatic polycondensation to synthesize mPEG‐functionalized poly(amine‐co‐ester)‐type chiral prodrugs |
title_sort |
tandem dynamic kinetic resolution and enzymatic polycondensation to synthesize mpeg‐functionalized poly(amine‐co‐ester)‐type chiral prodrugs |
publisher |
Wiley |
publishDate |
2013 |
url |
http://dx.doi.org/10.1002/pola.26594 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fpola.26594 https://onlinelibrary.wiley.com/doi/pdf/10.1002/pola.26594 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Journal of Polymer Science Part A: Polymer Chemistry volume 51, issue 9, page 2049-2057 ISSN 0887-624X 1099-0518 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/pola.26594 |
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Journal of Polymer Science Part A: Polymer Chemistry |
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51 |
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9 |
container_start_page |
2049 |
op_container_end_page |
2057 |
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1800742080368082944 |