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Transition-state mimicry by glycosidase inhibitors: a critical kinetic analysis.

作者信息

Wicki Jacqueline, Williams Spencer J, Withers Stephen G

机构信息

Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, Canada V6T 1Z1.

出版信息

J Am Chem Soc. 2007 Apr 18;129(15):4530-1. doi: 10.1021/ja0707254. Epub 2007 Mar 27.

DOI:10.1021/ja0707254

PMID:17385869

Abstract

摘要

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Transition-state mimicry by glycosidase inhibitors: a critical kinetic analysis.

作者信息

Wicki Jacqueline, Williams Spencer J, Withers Stephen G

机构信息

Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, Canada V6T 1Z1.

出版信息

J Am Chem Soc. 2007 Apr 18;129(15):4530-1. doi: 10.1021/ja0707254. Epub 2007 Mar 27.

DOI:10.1021/ja0707254

PMID:17385869

Abstract

摘要

相似文献

Transition-state mimicry by glycosidase inhibitors: a critical kinetic analysis.

J Am Chem Soc. 2007 Apr 18;129(15):4530-1. doi: 10.1021/ja0707254. Epub 2007 Mar 27.

Synthesis of thiohydantoin-castanospermine glycomimetics as glycosidase inhibitors.

J Org Chem. 2009 May 1;74(9):3595-8. doi: 10.1021/jo900231b.

Glycosidase inhibitors as conformational transition state analogues.

Chem Commun (Camb). 2007 Sep 28(36):3747-9. doi: 10.1039/b705607a. Epub 2007 Jun 28.

Glycosidase inhibition: assessing mimicry of the transition state.

Org Biomol Chem. 2010 Jan 21;8(2):305-20. doi: 10.1039/b915870g. Epub 2009 Nov 5.

Specificity fingerprinting of retaining beta-1,4-glycanases in the Cellulomonas fimi secretome using two fluorescent mechanism-based probes.

Chembiochem. 2007 Nov 23;8(17):2125-32. doi: 10.1002/cbic.200700481.

Glycosidase profiling with immobilised glycosidase-inhibiting iminoalditols--a proof-of-concept study.

Bioorg Med Chem Lett. 2008 Mar 15;18(6):1922-5. doi: 10.1016/j.bmcl.2008.01.124. Epub 2008 Feb 7.

Enzyme inhibition by iminosugars: analysis and insight into the glycosidase-iminosugar dependency of pH.

Bioorg Med Chem. 2013 Aug 15;21(16):4755-61. doi: 10.1016/j.bmc.2013.03.003. Epub 2013 Mar 15.

Advances in the synthesis of calystegines and related products and their biochemical properties.

Mini Rev Med Chem. 2012 Dec;12(14):1477-84. doi: 10.2174/138955712803832708.

Synthesis and conformational analysis of bicyclic sulfonium salts. Structures related to the glycosidase inhibitor australine.

J Org Chem. 2006 Apr 14;71(8):2935-43. doi: 10.1021/jo051560p.

Skeletal rearrangement of seven-membered iminosugars: synthesis of (-)-adenophorine, (-)-1-epi-adenophorine and derivatives and evaluation as glycosidase inhibitors.

Bioorg Med Chem. 2013 Aug 15;21(16):4803-12. doi: 10.1016/j.bmc.2013.03.035. Epub 2013 Apr 2.

引用本文的文献

Probing Monotopic Phosphoglycosyl Transferases from Complex Cellular Milieu.

ACS Chem Biol. 2022 Nov 18;17(11):3191-3197. doi: 10.1021/acschembio.2c00648. Epub 2022 Nov 8.

Glycoside Hydrolases Restrict the Side Chain Conformation of Their Substrates To Gain Additional Transition State Stabilization.

J Am Chem Soc. 2020 Oct 7;142(40):16965-16973. doi: 10.1021/jacs.0c05592. Epub 2020 Sep 24.

Determination of protonation states of iminosugar-enzyme complexes using photoinduced electron transfer.

Chem Sci. 2017 Nov 1;8(11):7383-7393. doi: 10.1039/c7sc01540b. Epub 2017 Sep 14.

Free Energy Diagram for the Heterogeneous Enzymatic Hydrolysis of Glycosidic Bonds in Cellulose.

J Biol Chem. 2015 Sep 4;290(36):22203-11. doi: 10.1074/jbc.M115.659656. Epub 2015 Jul 16.

Solution and gas-phase H/D exchange of protein-small-molecule complexes: Cex and its inhibitors.

J Am Soc Mass Spectrom. 2012 Jan;23(1):57-67. doi: 10.1007/s13361-011-0263-0. Epub 2011 Oct 18.

Mechanism, Structure, and Inhibition of O-GlcNAc Processing Enzymes.

Curr Signal Transduct Ther. 2010 Jan;5(1):74-91. doi: 10.2174/157436210790226537.

Glycosidase inhibition: assessing mimicry of the transition state.

Org Biomol Chem. 2010 Jan 21;8(2):305-20. doi: 10.1039/b915870g. Epub 2009 Nov 5.

Catalytic mechanism of human alpha-galactosidase.

J Biol Chem. 2010 Feb 5;285(6):3625-3632. doi: 10.1074/jbc.M109.060145. Epub 2009 Nov 25.

The effect of electrostatic interactions on conformational equilibria of multiply substituted tetrahydropyran oxocarbenium ions.

J Org Chem. 2009 Jan 16;74(2):545-53. doi: 10.1021/jo8017846.