（S）-硫杂环丙烷羧酸作为一类新型半胱氨酸蛋白酶抑制剂的反应性结构单元。

(S)-Thiirancarboxylic acid as a reactive building block for a new class of cysteine protease inhibitors.

作者信息

Schirmeister T

机构信息

Institute for Pharmacy and Food Chemistry, University of Würzburg, Germany.

出版信息

Bioorg Med Chem Lett. 2000 Dec 4;10(23):2647-51. doi: 10.1016/s0960-894x(00)00549-7.

DOI:10.1016/s0960-894x(00)00549-7

PMID:11128643

Abstract

For (S)-thiirancarboxylic acid a second-order rate constant of k2nd = 222 M(-1) min(-1) for the irreversible inhibition of papain was determined. The ethyl and methyl ester do not inhibit the enzyme time-dependently. An improved synthesis of enantiomerically pure thiirancarboxylic acid is described. It is shown that thiirancarboxylates can be substrates for serine proteases (alpha-chymotrypsin) and esterases (pig liver esterase) and even for metallo proteases (thermolysin).

摘要

对于（S）-硫代环丙烷羧酸，测定了其对木瓜蛋白酶不可逆抑制的二级速率常数k2nd = 222 M⁻¹ min⁻¹。乙酯和甲酯不会随时间依赖性地抑制该酶。描述了对映体纯硫代环丙烷羧酸的改进合成方法。结果表明，硫代环丙烷羧酸盐可以作为丝氨酸蛋白酶（α-胰凝乳蛋白酶）、酯酶（猪肝酯酶）甚至金属蛋白酶（嗜热菌蛋白酶）的底物。