Literature DB >> 29711789

Recent Insights into Inhibition, Structure, and Mechanism of Configuration-Retaining Glycosidases.

Tom D Heightman1, Andrea T Vasella1.   

Abstract

Not "from above", but "from the side": Configuration-retaining β-glycosidases protonate their substrate either anti or syn to the endocyclic C1-O bond as the first step in the enzymic cleavage of the glycosidic bond (see schematic drawing). Insights into the mechanism of action of glycosidases have been gained by a combination of the synthesis of inhibitors, the study of the kinetics of their inhibition, and the analysis of the crystal structures of glycosidases and glycosidase-ligand complexes. © 1999 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.

Entities:  

Keywords:  Azoles; Enzyme inhibitors; Glycosidases; Lactams; Protonations

Year:  1999        PMID: 29711789     DOI: 10.1002/(SICI)1521-3773(19990315)38:6<750::AID-ANIE750>3.0.CO;2-6

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  21 in total

1.  Structural analysis of Thermus thermophilus HB27 mannosyl-3-phosphoglycerate synthase provides evidence for a second catalytic metal ion and new insight into the retaining mechanism of glycosyltransferases.

Authors:  Susana Gonçalves; Nuno Borges; Ana M Esteves; Bruno L Victor; Cláudio M Soares; Helena Santos; Pedro M Matias
Journal:  J Biol Chem       Date:  2010-03-31       Impact factor: 5.157

2.  GlcNAcstatin: a picomolar, selective O-GlcNAcase inhibitor that modulates intracellular O-glcNAcylation levels.

Authors:  Helge C Dorfmueller; Vladimir S Borodkin; Marianne Schimpl; Sharon M Shepherd; Natalia A Shpiro; Daan M F van Aalten
Journal:  J Am Chem Soc       Date:  2006-12-27       Impact factor: 15.419

Review 3.  Glycosidase inhibition: assessing mimicry of the transition state.

Authors:  Tracey M Gloster; Gideon J Davies
Journal:  Org Biomol Chem       Date:  2009-11-05       Impact factor: 3.876

4.  Synthesis of lipophilic 1-deoxygalactonojirimycin derivatives as D-galactosidase inhibitors.

Authors:  Georg Schitter; Elisabeth Scheucher; Andreas J Steiner; Arnold E Stütz; Martin Thonhofer; Chris A Tarling; Stephen G Withers; Jacqueline Wicki; Katrin Fantur; Eduard Paschke; Don J Mahuran; Brigitte A Rigat; Michael Tropak; Tanja M Wrodnigg
Journal:  Beilstein J Org Chem       Date:  2010-03-01       Impact factor: 2.883

5.  Synthesis of a new class of aminocyclitol analogues with the conduramine D-2 configuration.

Authors:  Latif Kelebekli; Yunus Kara; Murat Celik
Journal:  Beilstein J Org Chem       Date:  2010-02-15       Impact factor: 2.883

6.  Molecular basis of arabinobio-hydrolase activity in phytopathogenic fungi: crystal structure and catalytic mechanism of Fusarium graminearum GH93 exo-alpha-L-arabinanase.

Authors:  Raphaël Carapito; Anne Imberty; Jean-Marc Jeltsch; Simon C Byrns; Pui-Hang Tam; Todd L Lowary; Annabelle Varrot; Vincent Phalip
Journal:  J Biol Chem       Date:  2009-03-06       Impact factor: 5.157

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

Authors:  Jonathan C K Quirke; David Crich
Journal:  J Am Chem Soc       Date:  2020-09-24       Impact factor: 15.419

8.  An efficient and versatile synthesis of GlcNAcstatins-potent and selective O-GlcNAcase inhibitors built on the tetrahydroimidazo[1,2-a]pyridine scaffold.

Authors:  Vladimir S Borodkin; Daan M F van Aalten
Journal:  Tetrahedron       Date:  2010-09-25       Impact factor: 2.457

9.  Side Chain Conformation Restriction in the Catalysis of Glycosidic Bond Formation by Leloir Glycosyltransferases, Glycoside Phosphorylases, and Transglycosidases.

Authors:  Jonathan C K Quirke; David Crich
Journal:  ACS Catal       Date:  2021-04-13       Impact factor: 13.084

10.  Carbohydrate-Protein Interactions: Advances and Challenges.

Authors:  Shuang Zhang; Kyle Yu Chen; Xiaoqin Zou
Journal:  Commun Inf Syst       Date:  2021
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