Synthesis and triplex forming properties of an acyclic N7-glycosylated guanine nucleoside.
A chiral acyclic nucleoside, one in which the ribose carbohydrate has been replaced with a glycerol-based linker, is prepared by glycosylating guanine at the N7-nitrogen. The stereochemically pure derivative is converted to a DMT-protected phosphoramidite for incorporation into DNA sequences. Sequence containing the acyclic N7-dG nucleoside are capable of forming DNA triplexes in which it is likely that the N1-H and N2-amino groups of the N7-dG are involved in recognition of the guanine base in G-C base pairs.
St Clair
A
A
Department of Chemistry, Merkert Chemistry Center, Chestnut Hill, MA 02167, USA.
Xiang
G
G
McLaughlin
L W
LW
D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000737:chemistry; D006031:Glycosylation; D006147:Guanine; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009705:Nucleosides / Q000138:chemical synthesis*
D009705:Nucleosides; C051802:triplex DNA; D006147:Guanine; D004247:DNA