title: Design and synthesis of LNA-based mercaptoacetamido-linked nucleoside dimers.
abstract: Three LNA-based mercaptoacetamido-linked nonionic nucleoside dimers TL-S-T, T-S-TL, and TL-S-TL have been synthesized by HOBT and HBTU catalyzed condensation of silyl-protected 2-S-(thymidin-5 '-yl)mercaptoacetic acid or 2-S-(2 '-O,4 '-C-methylenethymidin-5 '-yl)mercaptoacetic acid with 3 '-amino-3 '-deoxy-5 '-O-DMT-2 '-O,4 '-C-methylenethymidine or with 3 '-amino-3 '-deoxy-5 '-O-DMT-β-thymidine followed by desilylation of the protected dimers. The 3 '-O-phosphoramidite derivative of one of the nucleoside dimers was successfully prepared by condensation with [P(-Cl)(-OCH2CH2CN)-N(iPr)2}] in DCM in the presence of N,N-diisopropylethylamine (DIPEA), which is a building block for the preparation of mercaptoacetamido-linked oligonucleotides of therapeutic applications.
authors.affiliation: Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi, India.
authors.forename: Vivek K
authors.initials: VK
authors.lastname: Sharma
authors.forename: Sunil K
authors.initials: SK
authors.lastname: Singh
authors.forename: Kapil
authors.initials: K
authors.lastname: Bohra
authors.forename: Chandra Shekhar Reddy
authors.initials: CS
authors.lastname: L
authors.forename: Vinod
authors.initials: V
authors.lastname: Khatri
authors.forename: Carl E
authors.initials: CE
authors.lastname: Olsen
authors.forename: Ashok K
authors.initials: AK
authors.lastname: Prasad
mesh_terms: D060326:Chemistry Techniques, Synthetic; D019281:Dimerization; D015195:Drug Design; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D009705:Nucleosides; D009841:Oligonucleotides; D013438:Sulfhydryl Compounds; C477371:locked nucleic acid