组氨酸、组胺和咪唑作为糖苷酶抑制剂。
Histidines, histamines and imidazoles as glycosidase inhibitors.
作者信息
Field R A, Haines A H, Chrystal E J, Luszniak M C
机构信息
School of Chemical Sciences, University of East Anglia, Norwich, U.K.
出版信息
Biochem J. 1991 Mar 15;274 ( Pt 3)(Pt 3):885-9. doi: 10.1042/bj2740885.
Abstract
This present study reports the ability of a range of derivatives of L-histidine, histamine and imidazole to act as inhibitors of sweet-almond beta-glucosidase, yeast alpha-glucosidase and Escherichia coli beta-galactosidase. The addition of a hydrophobic group to the basic imidazole nucleus greatly enhances binding to both the alpha- and beta-glucosidases. L-Histidine (beta-naphthylamide (Ki 17 microM) is a potent competitive inhibitor of sweet-almond beta-glucosidase as is omega-N-acetylhistamine (K1 35 microM), which inhibits the sweet-almond beta-glucosidase at least 700 times more strongly than either yeast alpha-glucosidase or Escherichia coli beta-galactosidase, and suggests potential for the development of selective reversible beta-glucosidase inhibitors. A range of hydrophobic omega-N-acylhistamines were synthesized and shown to be among the most potent inhibitors of sweet-almond beta-glucosidase reported to date.
摘要
本研究报告了一系列L-组氨酸、组胺和咪唑衍生物作为甜杏仁β-葡萄糖苷酶、酵母α-葡萄糖苷酶和大肠杆菌β-半乳糖苷酶抑制剂的能力。在碱性咪唑核上添加疏水基团可大大增强与α-和β-葡萄糖苷酶的结合。L-组氨酸（β-萘酰胺，Ki为17微摩尔）是甜杏仁β-葡萄糖苷酶的有效竞争性抑制剂，ω-N-乙酰组胺（K1为35微摩尔）也是，它对甜杏仁β-葡萄糖苷酶的抑制作用比酵母α-葡萄糖苷酶或大肠杆菌β-半乳糖苷酶至少强700倍，这表明开发选择性可逆β-葡萄糖苷酶抑制剂具有潜力。合成了一系列疏水的ω-N-酰基组胺，结果表明它们是迄今为止报道的最有效的甜杏仁β-葡萄糖苷酶抑制剂之一。
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