Syn/anti lateral protonation

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• Author: ^^^Wim Nerinckx^^^
• Responsible Curator: ^^^Spencer Williams^^^

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Overview

This page will provide a table (and eventually a full lexicon article) on the spatial positioning of the catalytic general acid residue in the active sites of glycoside hydrolases. The table below updates those found in the seminal paper on this concept by Heightman and Vasella [1], and the more recent summary by Nerinckx et al. [2].

Table

This table can be re-sorted by clicking on the icons in the header (javascript must be turned on in your browser). To reset the page to be sorted by GH family, click the page above the page title.

Family	Clan	Structure fold	Anomeric specificity	Mechanism	General acid	syn/anti	Nucleophile or General base	Ligand	Organism	Enzyme	PDB ID	Primary reference
GH1	A	(β/α)8	beta	retaining	Glu160	anti	Glu375	product	Lactococcus lactis	6-phosopho-beta-galactosidase	4pbg	[3]
GH2	A	(β/α)8	beta	retaining	Glu461	anti	Glu537	2-F-galactosyl	Escherechia coli	beta-galactosidase	1jz0	[4]
GH3	none	(β/α)8	beta	retaining	Glu491	anti	Asp285	2-F-glucosyl	Hordeum vulgare	exo-1,3-1,4-glucanase	1iew	[5]
GH9	none	(α/α)6	beta	inverting	Glu424	syn	Asp55,Asp58	product	Thermomonospora fusca	cellulase	3tf4,4tf4	[6]

References

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1. Heightman, T.D. and Vasella, A.T. (1999) Recent Insights into Inhibition, Structure, and Mechanism of Configuration-Retaining Glycosidases. Angewandte Chemie-International Edition 38(6), 750-770. Article online.

2. Nerinckx W, Desmet T, Piens K, and Claeyssens M. (2005). An elaboration on the syn-anti proton donor concept of glycoside hydrolases: electrostatic stabilisation of the transition state as a general strategy. FEBS Lett. 2005;579(2):302-12. DOI:10.1016/j.febslet.2004.12.021 |
5. Hrmova M, Varghese JN, De Gori R, Smith BJ, Driguez H, and Fincher GB. (2001). Catalytic mechanisms and reaction intermediates along the hydrolytic pathway of a plant beta-D-glucan glucohydrolase. Structure. 2001;9(11):1005-16. DOI:10.1016/s0969-2126(01)00673-6 |