Synthesis of nucleoside libraries on solid support. I. N2,N6-disubstituted diaminopurine nucleosides.
Starting with 2-iodo-6-chloro-9-(beta-D-ribofuranosyl)purine, a library of more than 1,300 N2,N6-polysubstituted diaminopurine nucleosides was created. The starting material was condensed with a polystyrene monomethoxytrityl resin and a pool of primary and secondary amines was used to displace the 6-chloro atom with high regioselectivity. The 2-iodo was subsequently displaced by various primary amines. Nucleosides were cleaved from the resin with hexafluoroisopropanol solutions. A majority of compounds reached a purity of more than 80% without the need for any type of purification.
Gunic
Esmir
E
Ribapharm, Inc., Costa Mesa, California 92626, USA.
Amador
Roberto
R
Rong
Frank
F
Abt
Jeffrey W
JW
An
Haoyun
H
Hong
Zhi
Z
Girardet
Jean-Luc
JL
D009682:Magnetic Resonance Spectroscopy; D011137:Polystyrenes / Q000737:chemistry; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry
D011137:Polystyrenes; D011684:Purine Nucleosides