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Sci. Pharm. 2014, 82(1), 1-20; doi:10.3797/scipharm.1308-03

Regioselective Synthesis, Characterization, and Antimicrobial Activities of Some New Monosaccharide Derivatives

1
Laboratory of Carbohydrate and Protein Chemistry, Department of Chemistry, Faculty of Science, University of Chittagong, Chittagong-4331, Bangladesh.
2
Department of Microbiology, Faculty of Biological Science, University of Chittagong, Chittagong-4331, Bangladesh.
3
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.
4
Laboratory of Glycobiology and Marine Biochemistry, Department of Genome System Sciences, Graduate School of Nanobiosciences, Yokohama City University, Yokohama 236-0027, Japan.
*
Author to whom correspondence should be addressed.
Received: 3 August 2013 / Accepted: 26 September 2013 / Published: 26 September 2013
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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, 1H-NMR, 13C-NMR, 13C-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) ex-hibited 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.
Keywords: Glucopyranosides; Synthesis; Derivatives; Elucidation; Spectroscopy; Antimicrobial Glucopyranosides; Synthesis; Derivatives; Elucidation; Spectroscopy; Antimicrobial
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

KAWSAR, S.M.A.; FARUK, M.O.; RAHMAN, M.S.; FUJII, Y.; OZEKI, Y. Regioselective Synthesis, Characterization, and Antimicrobial Activities of Some New Monosaccharide Derivatives. Sci. Pharm. 2014, 82, 1-20.

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