Synthesis of a dinucleoside monophosphate analogue containing 6-N-(2-aminoethyl)-2′-deoxyadenosine. A novel approach to sequence specific cross-linking in synthetic oligonucleotides

Abstract

The incorporation of 6-N-(2-aminoethyl)-2′-deoxyadenosine 1 into 6-N-(2-aminoethyl)-2′-deoxyadenylyl-(3′-5′)-thymidine 2 using a phosphoramidite intermediate is described. The trifluoroacetyl group is demonstrated to be an ideal protecting group for the amino function whilst the 4,4′-dimethoxytrityl group is utilised to block the 5′-hydroxy function. This study serves as a model investigation for the incorporation of compound 1 into oligodeoxynucleotides to investigate their potential for forming sequency specific interstrand cross-links.