Vibrational normal modes calculation in the crystalline state of methylated monosaccharides: Anomers of the methyl-d-glucopyranoside and methyl-d-xylopyranoside molecules

Taleb-Mokhtari, I.N.; Lazreg, A.; Sekkal-Rahal, Majda; Bestaoui, Noreya

doi:10.1016/j.saa.2015.08.038

Cited by 4 publications

(5 citation statements)

References 18 publications

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“…The IR spectrum of this compound showed the following characteristic peaks: 1738 cmG 1 (-CO stretching), 3510 cmG 1 (-OH stretching), 3320 cmG 1 (-NH stretching) and 1365 cmG 1 (-SO 2 stretching). The IR spectra of the synthesized compounds were accordance to the IR values of which were stated in the literature (Taleb-Mokhtari et al, 2016;Brauer et al, 2011). In its 1 H-NMR spectrum displayed two two-proton doublets at d 7.70 (J = 8.8 Hz) and d 7.68 (J = 8.8 Hz) corresponding to the aromatic ring protons, one one-proton singlet at d 7.53 (-NH), one three-proton singlet at d 2.22 (-NCOCH 3 ) thereby suggesting the introduction of one N-acetylsulfanilyl (4-acetamidobenzenesulfonyl) group in the molecule.…”

Section: Chemistry and Spectral Characterizationsupporting

confidence: 79%

“…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%

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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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Section: Chemistry and Spectral Characterizationsupporting

confidence: 79%

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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“…The structure of the benzenesulfonyl derivative (2) was established by , thereby suggesting the presence of carbonyl, hydroxyl and sulfonyl groups in the molecule. The IR spectra of the synthesized compounds are similar to the IR values of which were stated in the study of (Taleb-Mokhtari et al (2016) and Brauer et al (2011). In its 1 H-NMR spectrum, the peaks at δ 7.90 (2H, m), δ 7.70 (1H, m) and δ 7.50 (2H, m) corresponded the protons of one phenyl group.…”

Section: Spectral Characterization Of Benzenesulfonyl-α-d-glucopyranosupporting

confidence: 78%

“…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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“…The vibrational frequencies calculated at the B3LYP/aug‐cc‐pVDZ level were scaled by a scaling factor of 0.9704 as recommended by Scott and Radom . In addition, reliable vibrational assignments were carried out on the potential energy distribution (PED) basis . The assignment of the calculated wave numbers could be easily made thanks to the Gauss‐View graphical interface for Gaussian programs, allowing a visual representation of the shape of the vibrational modes.…”

Section: Computational Detailssupporting

confidence: 56%

Density Functional Theory Investigations on Vibrational Spectra, Molecular Structure, and Properties of the L-Serine, L-Cysteine, and L-Aspartic Acid Molecules

Lazreg

Taleb-Mokhtari

Yousfi

et al. 2017

Journal of the Chinese Chemical Society

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In this paper, we present a thorough investigation of the conformational space to characterize all possible gas‐phase structures of the neutral L‐serine, L‐cysteine, and L‐aspartic acid molecules. A total of 120 trial structures were generated for L‐aspartic acid and 96 trial structures for L‐serine and L‐cysteine by combining all internal single‐bond rotamers. Various combinations of the Hartree–Fock and density functional theory/B3LYP methods with different bases were used to optimize all possible trial structures. The theoretical studies on the structure, harmonic vibrational spectra, and molecular properties of these amino acids are presented. The assignments of the calculated wave numbers resulting from potential energy distributions were performed using the VEDA 4 program to allow a good interpretation of the theoretical vibrational spectra of the title compounds. The fundamental harmonic frequencies were found to be in good agreement with data in the literature. A natural bond orbital analysis was performed to investigate the charge delocalization throughout the molecules for the three test compounds. Moreover, an extensive discussion of the highest occupied molecular orbital–lowest unoccupied molecular orbital energy gap as well as other related molecular properties are reported.

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Vibrational normal modes calculation in the crystalline state of methylated monosaccharides: Anomers of the methyl-d-glucopyranoside and methyl-d-xylopyranoside molecules

Cited by 4 publications

References 18 publications

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

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

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

Density Functional Theory Investigations on Vibrational Spectra, Molecular Structure, and Properties of the L-Serine, L-Cysteine, and L-Aspartic Acid Molecules

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