Synthesis of Cyclophellitol, Cyclophellitol Aziridine, and Their Tagged Derivatives

被引：30

作者：

Li, Kah-Yee ^{[1
]}

Jiang, Jianbing ^{[1
]}

Witte, Martin D. ^{[2
]}

Kallemeijn, Wouter W. ^{[3
]}

van den Elst, Hans ^{[1
]}

Wong, Chung-Sing ^{[1
]}

Chander, Sharina D. ^{[1
]}

Hoogendoorn, Sascha ^{[1
]}

Beenakker, Thomas J. M. ^{[1
]}

Codee, Jeroen D. C. ^{[1
]}

Aerts, Johannes M. F. G. ^{[3
]}

van der Marel, Gijs A. ^{[1
]}

Overkleeft, Herman S. ^{[1
]}

机构：

[1] Leiden Univ, Leiden Inst Chem, NL-2300 RA Leiden, Netherlands

[2] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands

[3] Univ Amsterdam, Acad Med Ctr, Dept Med Biochem, NL-1105 AZ Amsterdam, Netherlands

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 27期

基金：

欧洲研究理事会;

关键词：

Cyclitols; Enzyme inhibitors; Aziridines; Azides; Epoxides; Fluorescent probes; BETA-GLUCOSIDASE INHIBITOR; BODIPY DYES; IN-SITU; (+)-CYCLOPHELLITOL; BIOCHEMISTRY; CONVERSION; MECHANISM;

D O I：

10.1002/ejoc.201402588

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclitol epoxides and aziridines are potent and selective irreversible inhibitors of retaining glycosidases. We have previously reported on our studies on the use of activity-based probes derived from cyclophellitol and from its aziridine analogue for activity-based profiling of retaining -glucosidases in vitro, in situ, and in some examples also in vivo. In this work we disclose full details of the synthesis, purification, and analysis of a comprehensive panel of cyclophellitol analogues, all featuring the -glucose configuration and designed as tools for selective inhibition and/or imaging of human acid glucosylceramidase (epoxides) or as broad-spectrum probes for retaining -glucosidases (aziridines).

引用

页码：6030 / 6043

页数：14

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