5n0f

Publication Abstract from PubMed

The non-hydrolyzable S-linked azasugars, 1,6-alpha-mannosylthio- and 1,6-alpha-mannobiosylthioisofagomine, were synthesized and shown to bind with high affinity to a family 76 endo-1,6-alpha-mannanase from Bacillus circulans. X-ray crystallography showed an atypical interaction of the isofagomine nitrogen with the catalytic acid/base. Molecular dynamics simulations reveal that the atypical binding results from sulfur perturbing the most stable form away from the nucleophile interaction preferred for the O-linked congener.

An atypical interaction explains the high-affinity of a non-hydrolyzable S-linked 1,6-alpha-mannanase inhibitor.,Belz T, Jin Y, Coines J, Rovira C, Davies GJ, Williams SJ Chem Commun (Camb). 2017 Aug 25;53(66):9238-9241. doi: 10.1039/c7cc04977c. Epub, 2017 Aug 2. PMID:28766587^[1]

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.