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聚羟基脂肪酸酯(PHA)与含有羧基或羟基官能团的(生物)活性化合物共价结合形成低聚物的酯交换反应。

Transesterification of PHA to oligomers covalently bonded with (bio)active compounds containing either carboxyl or hydroxyl functionalities.

作者信息

Kwiecień Iwona, Radecka Iza, Kowalczuk Marek, Adamus Grażyna

机构信息

Centre of Polymer and Carbon Materials, Polish Academy of Sciences, Zabrze, Poland.

School of Biology, Chemistry and Forensic Science, Faculty of Science and Engineering, University of Wolverhampton, Wolverhampton, United Kingdom.

出版信息

PLoS One. 2015 Mar 17;10(3):e0120149. doi: 10.1371/journal.pone.0120149. eCollection 2015.

DOI:10.1371/journal.pone.0120149
PMID:25781908
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4363623/
Abstract

This manuscript presents the synthesis and structural characterisation of novel biodegradable polymeric controlled-release systems of pesticides with potentially higher resistance to weather conditions in comparison to conventional forms of pesticides. Two methods for the preparation of pesticide-oligomer conjugates using the transesterification reaction were developed. The first method of obtaining conjugates, which consist of bioactive compounds with the carboxyl group and polyhydroxyalkanoates (PHAs) oligomers, is "one-pot" transesterification. In the second method, conjugates of bioactive compounds with hydroxyl group and polyhydroxyalkanoates oligomers were obtained in two-step method, through cyclic poly(3-hydroxybutyrate) oligomers. The obtained pesticide-PHA conjugates were comprehensively characterised using GPC, 1H NMR and mass spectrometry techniques. The structural characterisation of the obtained products at the molecular level with the aid of mass spectrometry confirmed that both of the synthetic strategies employed led to the formation of conjugates in which selected pesticides were covalently bonded to PHA oligomers via a hydrolysable ester bond.

摘要

本手稿介绍了新型可生物降解聚合物农药控释系统的合成与结构表征,与传统农药形式相比,该系统对天气条件可能具有更高的耐受性。开发了两种利用酯交换反应制备农药 - 低聚物共轭物的方法。获得由具有羧基的生物活性化合物和聚羟基链烷酸酯(PHA)低聚物组成的共轭物的第一种方法是“一锅法”酯交换反应。在第二种方法中,通过环状聚(3 - 羟基丁酸酯)低聚物,采用两步法获得具有羟基的生物活性化合物与聚羟基链烷酸酯低聚物的共轭物。使用凝胶渗透色谱法(GPC)、核磁共振氢谱(1H NMR)和质谱技术对所得的农药 - PHA共轭物进行了全面表征。借助质谱在分子水平上对所得产物进行的结构表征证实,所采用的两种合成策略均导致形成了共轭物,其中选定的农药通过可水解的酯键与PHA低聚物共价结合。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/2c72eddfb3e7/pone.0120149.g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/06ca75188991/pone.0120149.g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/d7370e6e9c77/pone.0120149.g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/1300684de631/pone.0120149.g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/ef7ce3fc5b60/pone.0120149.g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/0549d004f77a/pone.0120149.g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/82a9df96be25/pone.0120149.g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/7ed7a61da003/pone.0120149.g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/2c72eddfb3e7/pone.0120149.g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/06ca75188991/pone.0120149.g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/d7370e6e9c77/pone.0120149.g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/1300684de631/pone.0120149.g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/ef7ce3fc5b60/pone.0120149.g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/0549d004f77a/pone.0120149.g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/82a9df96be25/pone.0120149.g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/7ed7a61da003/pone.0120149.g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fb9/4363623/2c72eddfb3e7/pone.0120149.g008.jpg

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