Bioorganic Chemistry p. 72 - 88 (1995)
Update date:2022-08-04
Topics:
Neumann
Guetschow
3,1-Benzothiazin-4-ones are sulfur analogs of the potent serine protease inactivators of the 3,1-benzoxazin-4-one type, which acylate the serine residue within the active site of the enzymes. A series of 2-amino-3,1-benzothiazinones was synthesized, but these compounds showed only very little inhibitory activity toward chymotrypsin, a model serine protease. Detailed investigations revealed that benzothiazinones and benzoxazinones react with identical mechanisms, but benzothiazinones acylate chymotrypsin with much lower rate constants. Investigations of nonenzymatic hydrolysis showed the benzothiazinones to be intrinsically more stable than benzoxazinones. It was concluded from spectroscopic results, that benzoxazinones are highly activated due to the absence of ester-like resonance. 2-Benzoylamino-4H-3,1-benzoxazin-4-one was found to be a new, highly active chymotrypsin inactivator. In contrast, benzothiazinones were found to be resonance stabilized. The contribution of a resonance structure with an exocyclic oxanion to the overall structure of the benzothiazinones and its nonproductive binding to the active site explained their low reactivity toward chymotrypsin.
View MoreNanjing Chemlin Chemical Co., Ltd.
website:http://www.echemlin.cn
Contact:+86-25-83697070
Address:Rm.902 Longyin Plaza, No. 217 Zhongshan Rd.(N) Nanjing 210009,China
website:http://www.china-sinoway.com
Contact:+86-592-5853819
Address:16/F,Huicheng Comm,Complex,No839 XiaHe Rd, Xiamen,China
website:http://www.fwdchem.com
Contact:86-21-54450828
Address:Room 802,Lotus Tower ,159 Tianzhou Road,Xuhui District,Shanghai
Shijiazhuang Yunxuan Im&Export Co.,Ltd.
Contact:+86-311-83037514
Address:No.6 Hongbin Road
Contact:+86-15995924277
Address:WuZhongOu suzhou new south road 89
Doi:10.5560/ZNB.2014-4002
(2014)Doi:10.1016/0040-4039(95)00082-N
(1995)Doi:10.1002/jhet.1779
(2014)Doi:10.1002/jhet.1106
(2014)Doi:10.1016/0022-328X(95)05396-7
(1995)Doi:10.1002/ejoc.200900167
(2009)