Synthesis of Oligonucleotides Containing the Alkali-Labile Pyrimidopurinone Adduct, M1G

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• 作者：Nathalie C. Schnetz-Boutaud ; Hui Mao ; Michael P. Stone ; and Lawrence J. Marnett
• 刊名：Chemical Research in Toxicology
• 出版年：2000
• 出版时间：February 2000
• 年：2000
• 卷：13
• 期：2
• 页码：90 - 95
• 全文大小：118K
• 年卷期：v.13,no.2(February 2000)
• ISSN：1520-5010

文摘

An improved method for the synthesis of oligodeoxyribonucleotides containing the endogenousadduct, pyrimido[1,2-a]purin-10(3H)-one (M₁G), is reported. The key features of the methodologyinclude improved synthesis of the deoxynucleoside of M₁G by transribosylation with deoxycytidine catalyzed by nucleoside 2'-deoxyribosyltransferase and the use of commerciallyavailable 4-tert-butylphenoxyacetyl protecting groups for normal nucleotides. Facile deprotectionand removal of the M₁G-containing oligomers from the solid support were achieved by treatmentwith a solution of potassium carbonate in methanol. NMR studies were performed to determinethe stability of the oligonucleotides at different pHs.