Powell Chadwick R, Foster Jeffrey C, Swilley Sarah N, Kaur Kuljeet, Scannelli Samantha J, Troya Diego, Matson John B
Department of Chemistry, Virginia Tech Center for Drug Discovery Macromolecules Innovation Institute 1040 Drillfield Dr., Blacksburg, VA 24061.
Polym Chem. 2019 Jun 21;10(23):2991-2995. doi: 10.1039/C9PY00354A. Epub 2019 Apr 24.
Herein we report the self-amplified depolymerization of an aryl oligo(thiourethane) (OTU) for the release of COS/HS. The OTU was synthesized via polyaddition of 4-isothiocyanatobenzyl alcohol and end-capped with an aryl azide. The aryl azide chain-end was reduced by tris(2-carboxyethyl)phosphine or HS to the corresponding aniline, resulting in depolymerization (i.e., self-immolation) and the release of COS/HS. Depolymerization was monitored by H NMR and UV-Vis spectroscopy, and the released COS was converted into HS by the ubiquitous enzyme carbonic anhydrase in aqueous media.
在此，我们报道了一种芳基低聚（硫代聚氨酯）（OTU）的自增强解聚反应，用于释放COS/HS。OTU通过4-异硫氰酸苄醇的加成聚合反应合成，并以芳基叠氮化物封端。芳基叠氮链端被三（2-羧乙基）膦或HS还原为相应的苯胺，导致解聚（即自牺牲）并释放COS/HS。通过核磁共振氢谱（1H NMR）和紫外可见光谱监测解聚过程，并且在水性介质中，释放出的COS被普遍存在的碳酸酐酶转化为HS。
