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Importance of hydroxyls at positions 3, 4, and 6 for binding to the "galactose" site of beta-galactosidase (Escherichia coli).3、4和6位羟基对于与β-半乳糖苷酶（大肠杆菌）的“半乳糖”位点结合的重要性。
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Synthesis of 5-amino-5-deoxy-D-mannopyranose and 1,5-dideoxy-1,5-imino-D-mannitol, and inhibition of alpha- and beta-D-mannosidases.5-氨基-5-脱氧-D-甘露吡喃糖和1,5-二脱氧-1,5-亚氨基-D-甘露糖醇的合成以及α-和β-D-甘露糖苷酶的抑制作用
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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.

DOI:10.1042/bj2740885
PMID:2012615
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1149993/
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。