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生物活性碳糖基胺的设计与合成：从糖苷酶抑制剂到药理学伴侣。

Design and synthesis of biologically active carbaglycosylamines: From glycosidase inhibitors to pharmacological chaperones.

机构信息

Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University.

Hokko Chemical Industry, Co., Ltd.

出版信息

Proc Jpn Acad Ser B Phys Biol Sci. 2022;98(7):336-360. doi: 10.2183/pjab.98.018.

DOI:10.2183/pjab.98.018
PMID:35908956
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9363598/
Abstract

For over 50 years, our group has been involved in synthetic studies on biologically active cyclitols including carbasugars. Among a variety of compounds synthesized, this review focuses on carbaglycosylamine glycosidase inhibitors, highlighting the following: (1) the naturally occurring N-linked carbaoligosaccharide α-amylase inhibitor acarbose and related compounds; (2) the novel synthetic β-glycosidase inhibitors, 1'-epi-acarviosin and its 6-hydroxy analogue as well as β-valienaminylceramide and its 4'-epimer; (3) the discovery of the β-glycosidase inhibitors with chaperone activity, N-octyl-β-valienamine (NOV) and its 4-epimer (NOEV); and (4) the recent development of the potential pharmacological chaperone N-alkyl-conduramine F-4 derivatives.

摘要

五十多年来，我们小组一直致力于具有生物活性的环糖醇（包括碳环糖）的合成研究。在合成的各种化合物中，本综述重点介绍了碳苷糖胺糖苷酶抑制剂，突出了以下几个方面：（1）天然存在的 N-连接碳寡糖α-淀粉酶抑制剂阿卡波糖及其相关化合物；（2）新型合成的β-糖苷酶抑制剂 1'-表阿卡维辛及其 6-羟基类似物以及β-戊烯胺基神经酰胺及其 4'-差向异构体；（3）发现具有伴侣活性的β-糖苷酶抑制剂，正辛基-β-戊烯胺（NOV）及其 4-差向异构体（NOEV）；（4）潜在的药理学伴侣 N-烷基-康杜胺 F-4 衍生物的最新进展。

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2
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Int J Mol Sci. 2020 Sep 19;21(18):6881. doi: 10.3390/ijms21186881.
3
Chaperone therapy for molecular pathology in lysosomal diseases.
分子病理学伴侣治疗溶酶体贮积症。
Brain Dev. 2021 Jan;43(1):45-54. doi: 10.1016/j.braindev.2020.06.015. Epub 2020 Jul 29.
4
Migalastat: A Review in Fabry Disease.米拉葡萄糖胺：法布瑞氏症的治疗选择。
Drugs. 2019 Apr;79(5):543-554. doi: 10.1007/s40265-019-01090-4.
5
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Nat Rev Dis Primers. 2018 Oct 1;4(1):27. doi: 10.1038/s41572-018-0025-4.
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ACS Chem Biol. 2016 Jun 17;11(6):1471-89. doi: 10.1021/acschembio.6b00195. Epub 2016 Apr 28.
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