Structural and mechanistic insights into a Bacteroides vulgatus retaining N-acetyl-β-galactosaminidase that uses neighbouring group participation

C. Roth; M. Petricevic; A. John; E. D. Goddard-Borger; G. J. Davies; S. J. Williams

doi:10.1039/C6CC04649E

Structural and mechanistic insights into a Bacteroides vulgatus retaining N-acetyl-β-galactosaminidase that uses neighbouring group participation†

C. Roth,^a M. Petricevic,^b A. John,^cd E. D. Goddard-Borger,*^cd G. J. Davies*^a and S. J. Williams*^b

Author affiliations

* Corresponding authors

^a Department of Chemistry, University of York, Heslington, York, UK
E-mail: gideon.davies@york.ac.uk

^b School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, Victoria, Australia
E-mail: sjwill@unimelb.edu.au

^c ACRF Chemical Biology Division, The Walter and Eliza Hall Institute of Medical Research, Parkville, Victoria, Australia
E-mail: goddard-borger.e@wehi.edu.au

^d Department of Medical Biology, University of Melbourne, Parkville, Victoria, Australia

Abstract

Bacteroides vulgatus is a member of the human microbiota whose abundance is increased in patients with Crohn's disease. We show that a B. vulgatus glycoside hydrolase from the carbohydrate active enzyme family GH123, BvGH123, is an N-acetyl-β-galactosaminidase that acts with retention of stereochemistry, and, through a 3-D structure in complex with Gal-thiazoline, provide evidence in support of a neighbouring group participation mechanism.

Supplementary files

Article information

DOI: https://doi.org/10.1039/C6CC04649E
Article type: Communication
Submitted: 03 Jun 2016
Accepted: 10 Aug 2016
First published: 15 Aug 2016
This article is Open Access

Download Citation

Chem. Commun., 2016,52, 11096-11099

Permissions

Request permissions

Structural and mechanistic insights into a Bacteroides vulgatus retaining N-acetyl-β-galactosaminidase that uses neighbouring group participation

C. Roth, M. Petricevic, A. John, E. D. Goddard-Borger, G. J. Davies and S. J. Williams, Chem. Commun., 2016, 52, 11096 DOI: 10.1039/C6CC04649E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Chemical Communications

Structural and mechanistic insights into a Bacteroides vulgatus retaining N-acetyl-β-galactosaminidase that uses neighbouring group participation†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Structural and mechanistic insights into a Bacteroides vulgatus retaining N-acetyl-β-galactosaminidase that uses neighbouring group participation

Social activity

Search articles by author

Spotlight

Advertisements