Synthesis of oligonucleotides containing the alkali-labile pyrimidopurinone adduct, M(1)G.
An improved method for the synthesis of oligodeoxyribonucleotides containing the endogenous adduct, pyrimido[1,2-a]purin-10(3H)-one (M(1)G), is reported. The key features of the methodology include improved synthesis of the deoxynucleoside of M(1)G by transribosylation with deoxycytidine catalyzed by nucleoside 2'-deoxyribosyltransferase and the use of commercially available 4-tert-butylphenoxyacetyl protecting groups for normal nucleotides. Facile deprotection and removal of the M(1)G-containing oligomers from the solid support were achieved by treatment with a solution of potassium carbonate in methanol. NMR studies were performed to determine the stability of the oligonucleotides at different pHs.
Schnetz-Boutaud
N C
NC
Department of Biochemistry, Center in Molecular Toxicology, and Vanderbilt-Ingram Cancer Center, Vanderbilt University, Nashville, Tennessee 37235, USA.
Mao
H
H
Stone
M P
MP
Marnett
L J
LJ
D000468:Alkalies / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D018736:DNA Adducts / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis*; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry
D000468:Alkalies; D018736:DNA Adducts; D009841:Oligonucleotides; D011687:Purines; D011743:Pyrimidines; C107643:pyrimido(1,2-a)purin-10(3H)-one