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Nucleic Acids Symposium Series 2006 50(1):7-8; doi:10.1093/nass/nrl004
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© 2006 Oxford University Press

A strategy for selective N-acylation of purine and pyrimidine bases of deoxy and ribo nucleosides

Roli Mishra, Satyendra Mishra, Vishnu Diwedi and Krishna Misra

Nucleic Acids Research Laboratory, Department of Chemistry, University of Allahabad, University of Allahabad, Allahabad-211002, India

A novel cost effective N-acylation procedure for exocyclic amino function of ribonucleosides (adenosine/guanosine/cytidine) and deoxynucleosides (adenosine/guanosine/cytidine) has been developed. In the present method the acids used for acylation were activated by preparing their corresponding p-nitrophenyl esters. These esters couple with - NH2 group in presence of dicyclohexylcarbodiimide as coupling agent and catalysts viz. DMAP, HOBT & HOSu to give the – CO - NH- bond; a well-established strategy in peptide synthesis. To minimise the contamination of DCU, different combinations of activated ester and nucleosides has been used. The use of catalysts viz. DMAP, HOBt & HOSu enhanced the yields. HOSu was found to give best results.


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