Tetrahedron Letters p. 3141 - 3144 (2001)
Update date:2022-08-05
Topics: -Synthesis
Volonterio, Alessandro
Bravo, Pierfrancesco
Zanda, Matteo
The synthesis of a novel family of partially-modified (PM) retropeptidyl hydroxamates incorporating a [CH(CF3)CH2CO] unit as a surrogate of the conventional malonyl group, has been accomplished both in solution and in solid-phase. The key step is the Michael-type N-addition of free or polymer bound α-amino hydroxamates to 3-(E-enoyl)-1,3-oxazolidin-2-ones, which takes place very effectively, although with low stereocontrol. A number of tri- and tetra-peptidyl hydroxamates were obtained either in diastereomerically pure form (by solution-phase synthesis, after chromatographic purification), or as mixtures of two epimers in very good chemical purity (by solid-phase, after release from the resin), demonstrating that this method is suitable for preparing combinatorial libraries of PM retro-ψ[NHCH(CF3)]-peptidyl hydroxamates for screening as metalloprotease inhibitors.
View MoreWuxi Highness Chemical Co.,Ltd
website:https://www.phtpharmatech.com/
Contact:86-510-81771080
Address:No58 East Xinguan Rd, Guanlin Town, Yixing City, Jiangsu China
Contact:+86 021-51698675
Address:1701, Jielong Plaza, No.618 Pingliang Rd, ShangHai,China
Hangzhou Zyter Biological & Chemical Technology Co., Ltd.
website:http://www.zyterpharm.com
Contact:+86-18858184290
Address:West Wenyi Road, Cangqian, Yuhang
ChangZhou XiaQing Chemical Co., Ltd.
Contact:+86-519-88721665
Address:3# Hengluo Road, Henglin Town, Changzhou City, Jiangsu Province,China
website:http://www.u-chemo.com
Contact:+86-21-61558312
Address:Dong Fang Road,
Doi:10.1002/macp.1959.020310116
(1959)Doi:10.1021/ol5018504
(2014)Doi:10.1002/ardp.19713041107
(1971)Doi:10.1002/hlca.19710540704
(1971)Doi:10.1039/j39710003557
(1971)Doi:10.3390/60500472
(2001)