Synthesis and Conformational Analysis of 2‐O‐Silyl Protected Nucleosides from Unprotected Nucleobases and Sugar Epoxides. Issue 28 (17th July 2020)

• Record Type: Journal Article
• Authors: Ahmed, Ajaz; Rasool, Faheem; Singh, Gurpreet; Katoch, Meenu; Mukherjee, Debaraj
• Is Part Of: European journal of organic chemistry. Issue 28(2020)
• Page Start: 4408
• Page End: 4416
• Publication Date: 2020-07-17
• Subjects: 1, 2‐Anhydro sugars -- 2‐Deoxy nucleosides -- Orthogonally protected -- Antibiofilm; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000650
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Synthesis of orthogonally protected 2‐silyl nucleosides were achieved by trans opening of sugar epoxides with nucleobases catalyzed by trimethylsilyltrifluoromethanesulfonate using hexamethyldisilazane both as solvent and silylating agent. Both α and β nucleosides were obtained with complete stereocontrol only by changing the epoxide stereochemistry. The synthesized nucleosides exist in different chair conformations depending upon the nature of protecting groups present in the sugar moiety as determined from coupling constants in the proton NMR. All the synthesized nucleosides were screened for biofilm inhibition activity against four bacterial pathogens and compound 7c was found to be most potent against Salmonella typhimurium with 1.22 µm biofilm inhibitory activity taking ciprofloxacin as control. Abstract : Silyl protected nucleosides possess better biological activity. 2‐ O ‐silylated nucleosides were synthesized by trans opening of 1, 2‐anhydrosugar with nucleobases where HMDS acts both as activating, and silylating agent. Conformational analysis and biofilm inhibition activity of synthesized nucleosides were performed.