Design and synthesis of a potential endoglycosidase inhibitor: Chemical conversion of N,N′-diacetylchitobiose into novel pseudodisaccharide containing a fivemembered cyclic N,N-dimethylguanidine

Article abstract of DOI:10.1246/cl.1996.97

(3aS,4R,5R,6R,6aS)-2-Dimethylamino-3a,5,6,6a-tetrahydro-4-hydroxy-6- hydroxymethyl-4H-cyclopentimidazole-5-yl 2-Acetamido-2-deoxy-β-D-glucopyranoside hydrochloride was designed as a potential inhibitor against endoglycosidases like lysozyme and chitinase, and was synthesized from N,N′-diacetylchitobiose by a series of reactions including radical cyclization of oxime ethers and cyclic guanidine-formation.