Synthesis of nucleoside libraries on solid support. II. 2,6,8-Trisubstituted purine nucleosides using 8-bromoguanosine as precursor.
A series of 2,6,8-trisubstituted purine nucleoside libraries was prepared by parallel solid-phase synthesis using 8-bromoguanosine as a common synthetic precursor. Polystyrene-methoxytrityl chloride resin was linked to the N2 or O5' position of the guanosine analogues. 8-Bromoguanosine was derivatized at the C8 position via carbon-carbon bond formation. Nucleophilic aromatic substitution at C2 and/or C6 positions with various amines produced two series of purine nucleoside libraries with very diverse substitution.
Koh
Yung-hyo
YH
Ribapharm, Inc., Costa Mesa, California 92626, USA.
Landesman
Michael B
MB
Amador
Roberto
R
Rong
Frank
F
An
Haoyun
H
Hong
Zhi
Z
Girardet
Jean-Luc
JL
D006151:Guanosine / Q000031:analogs & derivatives* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011137:Polystyrenes / Q000737:chemistry; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry
D011137:Polystyrenes; D011684:Purine Nucleosides; D006151:Guanosine; C035169:8-bromoguanosine