<i>Trans</i>-cyclosulfamidate mannose-configured cyclitol allows isoform-dependent inhibition of GH47 α-<scp>d</scp>-mannosidases through a bump

Trans-cyclosulfamidate mannose-configured cyclitol allows isoform-dependent inhibition of GH47 α-d-mannosidases through a bump–hole strategy

Published:2023 Issue:46 Volume:14 Page:13581-13586
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Males Alexandra¹^ORCID,Kok Ken²^ORCID,Nin-Hill Alba³⁴^ORCID,de Koster Nicky²,van den Beukel Sija²,Beenakker Thomas J. M.⁵^ORCID,van der Marel Gijsbert A.⁵,Codée Jeroen D. C.⁵^ORCID,Aerts Johannes M. F. G.²,Overkleeft Herman S.⁵^ORCID,Rovira Carme³⁴^ORCID,Davies Gideon J.¹^ORCID,Artola Marta²^ORCID

Affiliation:

1. York Structural Biology Laboratory, Department of Chemistry, The University of York, York YO10 5DD, UK

2. Department of Medical Biochemistry, Leiden Institute of Chemistry (LIC), Leiden University, P. O. Box 9502, 2300 RA Leiden, The Netherlands

3. Departament de Química Inorgànica i Orgànica (Secció de Química Orgànica), Institut de Química Teòrica i Computacional (IQTCUB), Universitat de Barcelona, Martí i Franquès 1, 08028 Barcelona, Spain

4. Fundació Catalana de Recerca i Estudis Avançats (ICREA), Passeig Lluís Companys 23, 08010 Barcelona, Spain

5. Department of Bio-organic Synthesis, Leiden Institute of Chemistry (LIC), Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands

Abstract

1,6-Trans-manno-cyclosulfamidate 6 inhibits selectively an L310S mutant of Caulobacter GH47 α-d-mannosidase by virtue of its 1C4 conformation and bump-and-hole strategy, enabling allele-specific inhibition within the GH47 α-mannosidase family.

Funder

Royal Society

Biotechnology and Biological Sciences Research Council

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/SC/D3SC05016E

Reference39 articles.

1. Carba-cyclophellitols Are Neutral Retaining-Glucosidase Inhibitors

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5. Covalent inhibitors of glycosidases and their applications in biochemistry and biology

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