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Open AccessArticle

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.
Sci. Pharm. 2014, 82(1), 1-20; https://doi.org/10.3797/scipharm.1308-03
Received: 3 August 2013 / Accepted: 26 September 2013 / Published: 26 September 2013
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
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. https://doi.org/10.3797/scipharm.1308-03

AMA Style

KAWSAR SMA, FARUK MO, RAHMAN MS, FUJII Y, OZEKI Y. Regioselective Synthesis, Characterization, and Antimicrobial Activities of Some New Monosaccharide Derivatives. Scientia Pharmaceutica. 2014; 82(1):1-20. https://doi.org/10.3797/scipharm.1308-03

Chicago/Turabian Style

KAWSAR, Sarkar M.A.; FARUK, Md O.; RAHMAN, Mohammad S.; FUJII, Yuki; OZEKI, Yasuhiro. 2014. "Regioselective Synthesis, Characterization, and Antimicrobial Activities of Some New Monosaccharide Derivatives" Sci. Pharm. 82, no. 1: 1-20. https://doi.org/10.3797/scipharm.1308-03

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