title: A novel thymidine phosphoramidite synthon for incorporation of internucleoside phosphate linkers during automated oligodeoxynucleotide synthesis.
abstract: A novel thymidine phosphoramidite synthon was synthesized and successfully used for incorporation of primary amino groups, attached through a triethylene glycol linker to the internucleoside phosphates, at desired locations during automated oligodeoxynucleotide synthesis. The synthesized amino-linker bearing oligonucleotides are stable under deprotection conditions and exhibit Watson-Crick base-pairing properties. Covalent labeling of oligonucleotides with carbocyanine near-infrared fluorochromes resulted in 2.5 times higher labeling yields when compared with oligonucleotides containing base-attached aminolinkers. We anticipate that the developed synthetic approach will be useful for nucleotide sequence-specific attachment of single or multiple ligands or reporter molecules.
authors.affiliation: Cancer Center, Massachusetts General Hospital, Charlestown, MA 02129, USA.
authors.forename: David
authors.initials: D
authors.lastname: Tabatadze
authors.forename: Paul
authors.initials: P
authors.lastname: Zamecnik
authors.forename: Ivan
authors.initials: I
authors.lastname: Yanachkov
authors.forename: George
authors.initials: G
authors.lastname: Wright
authors.forename: Katherine
authors.initials: K
authors.lastname: Pierson
authors.forename: Surong
authors.initials: S
authors.lastname: Zhang
authors.forename: Alexei
authors.initials: A
authors.lastname: Bogdanov
authors.forename: Valeri
authors.initials: V
authors.lastname: Metelev
mesh_terms: D020029:Base Pairing; D002232:Carbocyanines / Q000138:chemical synthesis / Q000737:chemistry; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013936:Thymidine / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002232:Carbocyanines; D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D013936:Thymidine