A novel thymidine phosphoramidite synthon for incorporation of internucleoside phosphate linkers during automated oligodeoxynucleotide synthesis.
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.
Tabatadze
David
D
Cancer Center, Massachusetts General Hospital, Charlestown, MA 02129, USA.
Zamecnik
Paul
P
Yanachkov
Ivan
I
Wright
George
G
Pierson
Katherine
K
Zhang
Surong
S
Bogdanov
Alexei
A
Metelev
Valeri
V
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
D002232:Carbocyanines; D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D013936:Thymidine