5MEH

Crystal structure of alpha-1,2-mannosidase from Caulobacter K31 strain in complex with 1-deoxymannojirimycin

Summary for 5MEH

• Entry DOI: 10.2210/pdb5meh/pdb
• Descriptor: Mannosyl-oligosaccharide 1,2-alpha-mannosidase, GLYCEROL, CALCIUM ION, ... (7 entities in total)
• Functional Keywords: glycoside hydrolase mannosidase, hydrolase
• Biological source: Caulobacter sp.
• Total number of polymer chains: 1
• Total formula weight: 51056.23

Authors

Males, A.,Davies, G.J. (deposition date: 2016-11-14, release date: 2016-12-21, Last modification date: 2024-05-08)

Primary citation

van Rijssel, E.R.,Janssen, A.P.A.,Males, A.,Davies, G.J.,van der Marel, G.A.,Overkleeft, H.S.,Codee, J.D.C.
Conformational Behaviour of Azasugars Based on Mannuronic Acid.
Chembiochem, 18:1297-1304, 2017

PubMed Abstract: A set of mannuronic-acid-based iminosugars, consisting of the C-5-carboxylic acid, methyl ester and amide analogues of 1deoxymannorjirimicin (DMJ), was synthesised and their pH-dependent conformational behaviour was studied. Under acidic conditions the methyl ester and the carboxylic acid adopted an "inverted" C chair conformation as opposed to the "normal" C chair at basic pH. This conformational change is explained in terms of the stereoelectronic effects of the ring substituents and it parallels the behaviour of the mannuronic acid ester oxocarbenium ion. Because of this solution-phase behaviour, the mannuronic acid ester azasugar was examined as an inhibitor for a Caulobacter GH47 mannosidase that hydrolyses its substrates by way of a reaction itinerary that proceeds through a H transition state. No binding was observed for the mannuronic acid ester azasugar, but sub-atomic resolution data were obtained for the DMJ⋅CkGH47 complex, showing two conformations- S and C -for the DMJ inhibitor.

PubMed: 28256791
DOI: 10.1002/cbic.201700080

Experimental method

X-RAY DIFFRACTION (0.95 Å)