2WC4

Structure of family 1 beta-glucosidase from Thermotoga maritima in complex with 3-imino-2-thia-(+)-castanospermine

Summary for 2WC4

• Entry DOI: 10.2210/pdb2wc4/pdb
• Related: 1OD0 1OIF 1OIM 1OIN 1UZ1 1W3J 2CBU 2CBV 2CES 2CET 2J75 2J77 2J78 2J79 2J7B 2J7C 2J7D 2J7E 2J7F 2J7G 2J7H 2JAL 2VRJ 2WBG 2WC3
• Descriptor: BETA-GLUCOSIDASE A, (3Z,5S,6R,7S,8R,8aS)-3-(octylimino)hexahydro[1,3]thiazolo[3,4-a]pyridine-5,6,7,8-tetrol, 1,2-ETHANEDIOL, ... (6 entities in total)
• Functional Keywords: castanospermine, glycoside hydrolase, polysaccharide degradation, cellulose degradation, carbohydrate metabolism, family 1, hydrolase, inhibitors, glycosidase
• Biological source: THERMOTOGA MARITIMA
• Total number of polymer chains: 4
• Total formula weight: 217604.04

Authors

Aguilar, M.,Gloster, T.M.,Turkenburg, J.P.,Garcia-Moreno, M.I.,Ortiz Mellet, C.,Davies, G.J.,Garcia Fernandez, J.M. (deposition date: 2009-03-08, release date: 2009-04-14, Last modification date: 2023-12-13)

Primary citation

Aguilar-Moncayo, M.,Gloster, T.M.,Turkenburg, J.P.,Garcia-Moreno, M.I.,Ortiz Mellet, C.,Davies, G.J.,Garcia Fernandez, J.M.
Glycosidase Inhibition by Ring-Modified Castanospermine Analogues: Tackling Enzyme Selectivity by Inhibitor Tailoring.
Org.Biomol.Chem., 7:2738-, 2009

PubMed Abstract: Synthesis of a panel of iso(thio)urea-type ring-modified castanospermine analogues bearing a freely mutarotating pseudoanomeric hydroxyl group results in tight-binding beta-glucosidase inhibitors with unusual binding signatures; the presence of an N-octyl substituent imparts a remarkable anomeric selectivity, promoting strong binding of the appropriate beta-anomer by the beta-glucosidase.

PubMed: 19532990
DOI: 10.1039/B906968B

Experimental method

X-RAY DIFFRACTION (1.7 Å)