A simple method for semi-synthesis of peptidyl-argininals as potent inhibitors of trypsin-like proteases.
A simple method for semi-synthesis of peptidyl-argininals as potent inhibitors of trypsin-like proteases.
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一种半合成肽基精氨酸作为胰蛋白酶样蛋白酶有效抑制剂的简单方法。
DOI：
10.1248/cpb.34.1748
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发表时间：
1986
影响因子：
1.7
通讯作者：
S. Ishii
中科院分区：
文献类型：
--
作者：
T. Someno;S. Ishii
建立了一种将胰肽素（乙酰-亮氨酸-亮氨酸-精氨酸）转化为其他肽基精氨酸的简便方法。用Pronase E酶切leupeptin dibutylacetal得到关键中间体精氨酸二丁酯（Argininal dibutylacetal），并在CM-52纤维素上进行柱层析分离。通过常规方法将n - α-阻断肽（或氨基酸）连接到该中间体的α-氨基上，最后用温和酸处理去除缩醛保护基团，恢复其必需的醛功能。该方法适用于多种肽基精氨酸的大规模制备，是胰蛋白酶家族蛋白酶的特异性抑制剂。
A simple method was developed for the conversion of leupeptin (acetyl-Leu-Leu-argininal) to other peptidyl argininals. Argininal dibutylacetal, a key intermediate, was produced by enzymatic digestion of leupeptin dibutylacetal with Pronase E and was isolated by column chromatography on CM-52 cellulose. Nα-Blocked peptides (or amino acids) were connected to the α-amino group of this intermediate by conventional methods, and finally the acetal protecting group was removed by mild acid treatment to recover the essential aldehyde function. This novel method is applicable to large-scale preparation of many kinds of peptidyl argininals, which are promising candidates as specific inhibitors of trypsin-family proteases.