title: Regioselective and stereoselective route to N2-β-tetrazolyl unnatural nucleosides via SN2 reaction at the anomeric center of Hoffer's chlorosugar.
abstract: We are reporting a regioselective and stereoselective route to N2-β-tetrazolyl aromatic donor/acceptor unnatural nucleosides as new class of possible DNA base analogs. The SN2 substitution reaction at the anomeric center of Hoffer's chlorosugar with various 5-substituted aromatic tetrazoles in THF in presence of K2CO3 proceeds with regioselectivity at N2-tetrazoles and stereoselectivity at α-chlorosugar with very good yield. The stereoelectronic and steric effects play a crucial role for the observed outcome which is also supported from a theoretical (DFT) study. The methodology is simple, eco-compatible and the tetrazolyl unnatural nucleosides might find applications in decorating DNA for various biotechnological and DNA based material science applications.
authors.affiliation: Bioorganic Chemistry Laboratory, Department of Chemistry, Indian Institute of Technology, Guwahati 781039, India. Electronic address: ssbag75@iitg.ernet.in.
authors.forename: Subhendu Sekhar
authors.initials: SS
authors.lastname: Bag
authors.affiliation: Bioorganic Chemistry Laboratory, Department of Chemistry, Indian Institute of Technology, Guwahati 781039, India.
authors.forename: Sangita
authors.initials: S
authors.lastname: Talukdar
authors.affiliation: Bioorganic Chemistry Laboratory, Department of Chemistry, Indian Institute of Technology, Guwahati 781039, India.
authors.forename: S J
authors.initials: SJ
authors.lastname: Anjali
mesh_terms: D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism; D013777:Tetrazoles / Q000737:chemistry*
chemical_list: D009705:Nucleosides; D013777:Tetrazoles
keywords: 2,5-Disubstituted tetrazoles; Regioselective; S(N)2 reaction; Stereoselective; Tetrazolyl-N2-β-nucleosides