Post-synthetic and site-specific modification of endocyclic nitrogen atoms of purines in DNA and its potential for biological and structural studies

Narukulla, Raman; Shuker, David E.G. and Xu, Yao-Zhong (2005). Post-synthetic and site-specific modification of endocyclic nitrogen atoms of purines in DNA and its potential for biological and structural studies. Nucleic Acids Research, 33(6), pp. 1767–1778.

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DOI (Digital Object Identifier) Link:	http://dx.doi.org/doi:10.1093/nar/gki315
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Abstract

Site-specific modification of the N1-position of purine was explored at the nucleoside and oligomer levels. 2'-Deoxyinosine was converted into an N1-2,4-dinitrophenyl derivative 2 that was readily transformed to the desired N1-substituted 2'-deoxyinosine analogues. This approach was used to develop a post-synthetic method for the modification of the endocyclic N1-position of purine at the oligomer level. The phosphoramidite monomer of N1-(2,4-dinitrophenyl)-2'-deoxyinosine 9 was prepared from 2'-deoxyinosine in four steps and incorporated into oligomers using an automated DNA synthesizer. The modified base, N1-(2,4-dinitrophenyl)-hypoxanthine, in synthesized oligomers, upon treatment with respective agents, was converted into corresponding N1-substituted hypoxanthines, including N1-15N-hypoxanthine, N1-methylhypoxanthine and N1-(2-aminoethyl)-hypoxanthine. These modified oligomers can be easily separated and high purity oligomers obtained. Melting curve studies show the oligomer containing N1-methylhypoxanthine or N1-(2-aminoethyl)-hypoxanthine has a reduced thermostability with no particular pairing preference to either cytosine or thymine. The developed method could be adapted for the preparation of oligomers containing mutagenic N1-ß-hydroxyalkyl-hypoxanthines and the availability of the rare base-modified oligomers should offer novel tools for biological and structural studies.

Item Type:	Journal Article
ISSN:	1362-4962
Extra Information:	Some of the symbols may not have transferred correctly into this bibliographic record.
Keywords:	purine; site-specific modification
Academic Unit/Department:	Science > Life, Health and Chemical Sciences
Item ID:	64
Depositing User:	Users 12 not found.
Date Deposited:	10 May 2006
Last Modified:	13 Dec 2010 11:12
URI:	http://oro.open.ac.uk/id/eprint/64

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