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The alkylation of 2'-deoxyguanosine and of thymidine with diazoalkanes. Some observations on o-alkylation.


ABSTRACT: The reaction in ether-methanol between 2'-deoxyguanosine and diazomethane or its ethyl or n-butyl homologue gives 1-, O(6)- and 7-alkyl-2'-deoxyguanosine. N(2),O(6)-Dimethyl-2'-deoxyguanosine was also detected. The hydrolysis of the methyl and the ethyl derivatives gives the corresponding alkylguanines: the O(6)-alkyl-2'-deoxyguanosines were sequentially hydrolysed, first to 2-amino-6-alkoxypurines, subsequently to guanine. The mass spectra of O(6)-alkyl-2'-deoxyguanosines (methyl and ethyl) and of the corresponding 2-amino-6-alkoxypurines were determined. The reaction of diazomethane with thymidine afforded O(4)-methylthymidine, in addition to the previously detected 3-methylthymidine.

SUBMITTER: Farmer PB 

PROVIDER: S-EPMC1165805 | BioStudies | 1973-01-01

SECONDARY ACCESSION(S): 10.1042/bj1350203

REPOSITORIES: biostudies

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