title: Regioselective synthesis, characterization, and antimicrobial activities of some new monosaccharide derivatives.
abstract: A regioselective acylation series of methyl α-D-glucopyranoside (1), methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside (1A), and methyl 4,6-O-benzylidene-2-O-(3,5-dinitrobenzoyl)-α-D-mannopyranoside (1B) has been carried out by the direct acylation method and afforded the 2,6-di-O-glucopyranoside and 2 or 3-O-mannopyranoside derivatives in an excellent yield. In order to obtain newer products, the 2,6-di-O-glucopyranoside derivative was further transformed to a series of 3,4-di-O-acyl derivatives containing a wide variety of functionalities in a single molecular framework. The structures of the newly synthesized compounds were elucidated on the basis of IR, (1)H-NMR, (13)C-NMR, (13)C-DEPT spectral data, and elemental analysis. These synthesized derivatives were screened for in vitro antimicrobial activities against ten human pathogenic and five phytopathogenic microorganisms. A number of test compounds showed remarkable antimicrobial activity comparable to, and in some cases even higher than, the standard antibiotics employed. It was observed that methyl 3,4-di-O-(3-chlorobenzoyl)-2,6-di-O-hexanoyl-α-D-glucopyranoside (8) exhibited a varied range of MIC from 12.5 μg/disc to 25 μg/disc by the disk diffusion method and 1000 μg/mL to 1250 μg/mL by the broth macrodilution method.
authors.affiliation: Laboratory of Carbohydrate and Protein Chemistry, Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong-4331, Bangladesh.
authors.forename: Sarkar M A
authors.initials: SM
authors.lastname: Kawsar
authors.affiliation: Laboratory of Carbohydrate and Protein Chemistry, Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong-4331, Bangladesh.
authors.forename: Md O
authors.initials: MO
authors.lastname: Faruk
authors.affiliation: Department of Microbiology, Faculty of Biological Science, University of Chittagong, Chittagong-4331, Bangladesh.
authors.forename: Mohammad S
authors.initials: MS
authors.lastname: Rahman
authors.affiliation: Divisions of Microbiology and Functional Morphology, Department of Pharmacy, Faculty of Pharmaceutical Science, Nagasaki International University, 2825-7 Huis Ten Bosch, Sasebo, Nagasaki 859-3298, Japan.
authors.forename: Yuki
authors.initials: Y
authors.lastname: Fujii
authors.affiliation: Laboratory of Glycobiology and Marine Biochemistry, Department of Genome System Sciences, Graduate School of Nanobiosciences, Yokohama City University, Yokohama 236-0027, Japan.
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Ozeki
keywords: Antimicrobial; Derivatives; Elucidation; Glucopyranosides; Spectroscopy; Synthesis