title: Synthesis, evaluation and molecular docking studies of amino acid derived N-glycoconjugates as antibacterial agents.
abstract: Six amino acid derived N-glycoconjugates of d-glucose were synthesized, characterized and tested for antibacterial activity against G(+)ve (Bacillus cereus) as well as G(-)ve (Escherichia coli and Klebsiella pneumoniae) bacterial strains. All the tested compounds exhibited moderate to good antibacterial activity against these bacterial strains. The results were compared with the antibacterial activity of standard drug Chloramphenicol, where results of A5 (Tryptophan derived glycoconjugates) against E. coli and A4 (Isoleucine derived glycoconjugates) against K. pneumoniae bacterial strains are comparable with the standard drug molecule. In silico docking studies were also performed in order to understand the mode of action and binding interactions of these molecules. The docking studies revealed that, occupation of compound A5 at the ATP binding site of subunit GyrB (DNA gyrase, PDB ID: 3TTZ) via hydrophobic and hydrogen bonding interactions may be the reason for its significant in vitro antibacterial activity.
authors.affiliation: Department of Chemistry, Birla Institute of Technology and Science, Pilani, Pilani Campus, Rajasthan 333031, India.
authors.forename: Noorullah
authors.initials: N
authors.lastname: Baig
authors.affiliation: Department of Biological Science, Birla Institute of Technology and Science, Pilani, Pilani Campus, Rajasthan 333031, India.
authors.forename: Rajnish Prakash
authors.initials: RP
authors.lastname: Singh
authors.affiliation: Department of Pharmacy, Birla Institute of Technology and Science, Pilani, Pilani Campus, Rajasthan 333031, India.
authors.forename: Subhash
authors.initials: S
authors.lastname: Chander
authors.affiliation: Department of Biological Science, Birla Institute of Technology and Science, Pilani, Pilani Campus, Rajasthan 333031, India.
authors.forename: Prabhat Nath
authors.initials: PN
authors.lastname: Jha
authors.affiliation: Department of Pharmacy, Birla Institute of Technology and Science, Pilani, Pilani Campus, Rajasthan 333031, India.
authors.forename: Sankaranarayanan
authors.initials: S
authors.lastname: Murugesan
authors.affiliation: Department of Chemistry, Birla Institute of Technology and Science, Pilani, Pilani Campus, Rajasthan 333031, India. Electronic address: asah@pilani.bits-pilani.ac.in.
authors.forename: Ajay K
authors.initials: AK
authors.lastname: Sah
mesh_terms: D000596:Amino Acids / Q000737:chemistry* / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004926:Escherichia coli / Q000187:drug effects; D005947:Glucose / Q000737:chemistry* / Q000494:pharmacology; D006001:Glycoconjugates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006860:Hydrogen Bonding; D057927:Hydrophobic and Hydrophilic Interactions; D007711:Klebsiella pneumoniae / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000596:Amino Acids; D000900:Anti-Bacterial Agents; D006001:Glycoconjugates; D005947:Glucose
keywords: Amino acids; Antibacterial; Glucopyranosylamine; Kinetics; Molecular docking; N-glycoconjugates