Synthesis of hexyl α-glucoside and α-polyglucosides by a novel Microbacterium isolate

Ojha, Swati; Mishra, Saroj; Kapoor, Sanjiv; Chand, Subhash

doi:10.1007/s00253-013-4855-4

Cited by 19 publications

(10 citation statements)

References 30 publications

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“…The acylated monosubstituted 2,3,4-tri-O-acyl derivatives (3-6 and 8-11) were synthesized from the corresponding substituted 6-O-benzenesulfonyl (2) and 6-O-N-acetylsulfanilyl (7) derivatives as previously described (Kawsar et al, 2014a). The structure of the various suitably substituted monosaccharide derivatives were ascertained by analyzing their FTIR (Taleb-Mokhtari et al, 2016;Brauer et al, 2011), 1 H-NMR (Loss and Lutteke, 2015;Ojha et al, 2013) spectra, elemental analysis and physicochemical properties (Table 1). All the acylation products were employed as test chemicals for antibacterial susceptibility studies against a number of human pathogenic bacteria.…”

Section: Results and Discussion Synthesismentioning

confidence: 99%

Synthesis, Characterization and Antibacterial Susceptibility of some Benzenesulfonyl and N-Acetylsulfanilyl Derivatives of Methyl α-D-Glucopyranoside

Kawsar¹,

Uddin²,

Nishat³

et al. 2015

Current Research in Chemistry

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A novel regioselective benzenesulphonylation and N-acetylsulfanilylation series of methyl α-D-glucopyranoside derivative (1) has been carried out by direct method and afforded the 6-O-benzenesulfonyl derivative (2) and 6-O-N-acetylsulfanilyl derivative (7) in an excellent yields. In order to obtain newer products, the 6-O-glucopyranoside derivative was further transformed to a series of 2,3,4-tri-O-acyl derivatives (3-6 and 8-11) containing a wide variety of functionalities in a single molecular framework. The structures of the newly synthesized compounds were elucidated with the aid of FTIR, 1 H-NMR spectroscopy and elemental analysis. All the synthesized compounds were also tested for their antibacterial activity against some human pathogenic bacterial microorganisms. For comparative studies, antibacterial activity of standard antibiotics, ampicillin was also carried out against these microorganisms. The study revealed that the acylated products exhibit moderate to good antimicrobial activities. It was interesting to observe that the selected compounds were more sensitive against gram-negative bacteria than that of the gram-positive bacterial strains. We carried out the antibacterial activities of the tested chemicals in vitro. In vivo screening studies of the tested compounds showing promising results will be the subject of our future investigation.

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Section: Results and Discussion Synthesismentioning

confidence: 99%

Synthesis, Characterization and Antibacterial Susceptibility of some Benzenesulfonyl and N-Acetylsulfanilyl Derivatives of Methyl α-D-Glucopyranoside

Kawsar¹,

Uddin²,

Nishat³

et al. 2015

Current Research in Chemistry

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“…Certain microbiota may be responsible for the production of digestive enzymes in some insects (Terra et al, 1996). M. paraoxydans, B. methylotrophicus and B. amyloliquefaciens isolated from S. litura larvae have already been known to produce digestive enzymes (Madhaiyan et al, 2010;Ojha et al, 2013;Saha et al, 2014). Higher abundance of these bacteria on S+ diet in comparison with S− diet may have resulted in increased level of digestive enzymes in larvae feeding on S+ diet.…”

Section: Treatmentsmentioning

confidence: 99%

Effect of antibiotic on survival and development ofSpodoptera litura(Lepidoptera: Noctuidae) and its gut microbial diversity

Thakur

Dhammi

Saini

et al. 2016

Bull. Entomol. Res.

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Addition of antibiotics to artificial diets of insects is a key component in the rearing of insects in the laboratory. In the present study an antimicrobial agent, streptomycin sulphate was tested for its influence on survival and fitness of Spodoptera litura (Fabricus) (Lepidoptera: Noctuidae) as well as its gut microbial diversity. The antibiotic did not adversely affect the survival of S. litura. Faster growth of larvae was recorded on diet amended with different concentrations of streptomycin sulphate (0.03, 0.07 and 0.15%) as compared to diet without streptomycin sulphate. The overall activity of various digestives enzymes increased on S+ diet while the activity of detoxifying enzymes significantly decreased. In addition, alteration in microbial diversity was found in the gut of S. litura larvae fed on diet supplemented with antibiotic (S+) and without antibiotic (S-).

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“…The resulting N-acetylsulfanilylation products (3) were converted to a number of derivatives using a series of acylating agents and their physicochemical properties are presented in the Table 2. The structure of the main acylation product and their derivatives were ascertained by analyzing their IR (Taleb-Mokhtari et al, 2016;Brauer et al, 2011) and 1 H-NMR (Loss and Lutteke, 2015;Ojha et al, 2013) spectra. All the acylation products thus prepared were employed as test chemicals for antibacterial activity studies against a number of Gram-positive and Gram-negative human pathogenic bacteria.…”

Section: Chemistry and Spectral Characterizationmentioning

confidence: 99%

Acylation of D-Glucose Derivatives over C5H5N: Spectral Characterization and in vitro Antibacterial Activities

Kawsar¹,

Uddin²,

Manchur³

et al. 2015

International J. of Biological Chemistry

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Methyl α-D-glucopyranoside was easily prepared by the treatment of D-glucose with anhydrous methyl alcohol in presence of hydrogen chloride at freezing temperature in good yield. Then N-acetylsulfanilylation of methyl α-D-glucopyranoside has been carried out by the direct method and afforded the 6-O-N-acetylsulfanilyl derivative in an excellent yield. In order to obtain newer products, the 6-O-N-acetylsulfanilyl derivative was further transformed to a series of 2,3,4-tri-O-acyl derivatives containing a wide variety of functionalities in a single molecular framework. The chemical structures of the newly synthesized compounds were elucidated by Fourier Transform Infrared spectroscopy (FTIR), 1 H-NMR (Proton nuclear magnetic resonance) spectroscopy elemental and physicochemical properties analysis. All the newly synthesized D-glucose derivatives were tested for their in vitro antibacterial activity against some human pathogenic bacterial strains. The study revealed that a good number of acylated products exhibited promising antibacterial activities. It is expected that the acylated derivatives of D-glucose may be considered as a potential source for developing new and better antibacterial agents against a number of pathogenic organism.

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Synthesis of hexyl α-glucoside and α-polyglucosides by a novel Microbacterium isolate

Cited by 19 publications

References 30 publications

Synthesis, Characterization and Antibacterial Susceptibility of some Benzenesulfonyl and N-Acetylsulfanilyl Derivatives of Methyl α-D-Glucopyranoside

Synthesis, Characterization and Antibacterial Susceptibility of some Benzenesulfonyl and N-Acetylsulfanilyl Derivatives of Methyl α-D-Glucopyranoside

Effect of antibiotic on survival and development ofSpodoptera litura(Lepidoptera: Noctuidae) and its gut microbial diversity

Acylation of D-Glucose Derivatives over C5H5N: Spectral Characterization and in vitro Antibacterial Activities

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