THE LOSSEN REARRANGEMENT IN BIOLOGICAL-SYSTEMS - INACTIVATION OF LEUKOCYTE ELASTASE AND ALPHA-CHYMOTRYPSIN BY (DL)-3-BENZYL-N-(METHANESULFONYLOXY) SUCCINIMIDE
THE LOSSEN REARRANGEMENT IN BIOLOGICAL-SYSTEMS - INACTIVATION OF LEUKOCYTE ELASTASE AND ALPHA-CHYMOTRYPSIN BY (DL)-3-BENZYL-N-(METHANESULFONYLOXY) SUCCINIMIDE
复制标题
DOI：
10.1016/s0006-291x(86)80235-2
复制
发表时间：
1986-12-15
影响因子：
3.1
通讯作者：
BRUBAKER, MJ
中科院分区：
文献类型：
--
作者：
GROUTAS, WC;GIRI, PK;BRUBAKER, MJ
已发现（dl）-3-苄基-N-（甲磺酰氧基）琥珀酰亚胺5有效且不可逆地抑制人白细胞弹性蛋白酶和α-胰凝乳蛋白酶。kobsd/[I]值分别为1170和9000 M-1 s-1。猪胰腺弹性蛋白酶不受5。化合物5可以构成丝氨酸蛋白酶的基于机制的抑制剂的第一个实例，其似乎通过前所未有的酶诱导的Lossen重排来发挥其作用。
(dl)-3-Benzyl-N-(methanesulfonyloxy)succinimide 5 has been found to inactivate human leukocyte elastase and alpha-chymotrypsin efficiently and irreversibly. The kobsd/[I] values were 1170 and 9000 M-1 s-1 respectively. Porcine pancreatic elastase was not inhibited by 5. Compound 5 may constitute the first example of a mechanism-based inhibitor of a serine proteinase that appears to exert its effect via an unprecedented enzyme-induced Lossen rearrangement.