A new method for the preparation of modified oligonucleotides.
[reaction-see text] N-Nitrothymidine can be transformed into a phosphoramidite building block suitable for oligonucleotide synthesis using the standard phosphite triester solid-phase approach. The N-nitrothymidine residues remain stable during the elongation cycles and react smoothly with primary amines, furnishing oligonucleotides containing N3-modified thymidines. A number of N3-substituted oligonucleotides have been prepared using this methodology, some of them incorporating aminoalkyl or hydroxyalkyl groups.
Gorchs
Olga
O
Departament de Química Orgànica, Universitat de Barcelona, Martí i Franquès 1, 08028 Barcelona, Spain.
Hernández
Marta
M
Garriga
Lourdes
L
Pedroso
Enrique
E
Grandas
Anna
A
Farràs
Jaume
J
D000588:Amines / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D007202:Indicators and Reagents; D009841:Oligonucleotides / Q000138:chemical synthesis*; D012116:Resins, Plant; D021241:Spectrometry, Mass, Electrospray Ionization; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D000588:Amines; D007202:Indicators and Reagents; D009841:Oligonucleotides; D012116:Resins, Plant; D006859:Hydrogen