Presentation Title

Synthesis and Bacterial Evaluation of 3’-sulfonaminde Nucleosides

Faculty Mentor

Dr. Ahmed Awad

Start Date

17-11-2018 12:30 PM

End Date

17-11-2018 2:30 PM

Location

CREVELING 22

Session

POSTER 2

Type of Presentation

Poster

Subject Area

physical_mathematical_sciences

Abstract

An antimicrobial agent is a substance that kills microorganism or inhibits their growth. The two most commonly used antibacterial are tobramycin and gentamicin. Both are aminoglycosides that are used to treat a wide variety of bacterial infections, particularly gram-negative bacteria like Pseudomonas and Escherichia coli. As these commonly used antimicrobial agents are used more frequently, bacteria strains that are resistant to one or multiple antibiotics are being found. The sulfonamide functional group is known to be used in antimicrobial agents as it binds to and inhibit enzymes critical to bacterial survival. In the current study, we are suggesting the attachment of sulfonamide derivatives to nucleosides in order to create an effective antimicrobial agent that can be used against bacteria strains that show resistance to already available drugs. Efficient synthesis of xylofuranosides by enantioselective reduction using Corey-Bakshi-Shibata (CBS) catalyst was reported. Replacement of the 3’-hydroxyl of uridine nucleoside with sulfonamide derivatives was performed via Mitsunobu reaction to produce analogues with desired configuration. Synthesized compounds were purified by silica gel column chromatography, and their structures were confirmed by NMR and HRMS. Future work will include testing and investigating these molecules as efficient antimicrobial agents.

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Nov 17th, 12:30 PM Nov 17th, 2:30 PM

Synthesis and Bacterial Evaluation of 3’-sulfonaminde Nucleosides

CREVELING 22

An antimicrobial agent is a substance that kills microorganism or inhibits their growth. The two most commonly used antibacterial are tobramycin and gentamicin. Both are aminoglycosides that are used to treat a wide variety of bacterial infections, particularly gram-negative bacteria like Pseudomonas and Escherichia coli. As these commonly used antimicrobial agents are used more frequently, bacteria strains that are resistant to one or multiple antibiotics are being found. The sulfonamide functional group is known to be used in antimicrobial agents as it binds to and inhibit enzymes critical to bacterial survival. In the current study, we are suggesting the attachment of sulfonamide derivatives to nucleosides in order to create an effective antimicrobial agent that can be used against bacteria strains that show resistance to already available drugs. Efficient synthesis of xylofuranosides by enantioselective reduction using Corey-Bakshi-Shibata (CBS) catalyst was reported. Replacement of the 3’-hydroxyl of uridine nucleoside with sulfonamide derivatives was performed via Mitsunobu reaction to produce analogues with desired configuration. Synthesized compounds were purified by silica gel column chromatography, and their structures were confirmed by NMR and HRMS. Future work will include testing and investigating these molecules as efficient antimicrobial agents.