The Spontaneous Rearrangement of 2,4-Dinitrophenyl Substituent in Ribonucleosides Under Neutral Conditions

Abstract

In the cytidine and adenosine derivatives an isomerization of a 2,4-dinitrophenyl group between the 2′- and 3′-positions of the ribose was observed under neutral conditions. Moreover, it was shown that isomerization of the 2,4-dinitrophenyl group in conditions required to synthesize phosphoramidites and lability in aqueous ammonia make chemical synthesis of 2′-O-(2,4-dinitrophenyl) oligonucleotides impossible.

Keywords:

• 2,4-Dinitrophenyl
• isomeration
• ribonucleosides
• Smiles rearrangement

Acknowledgments

This work was supported by the Ministry of Science and Higher Education, grants PBZ-MNiSW-07/I/2007 (R. K.) and N N301 3383 33 (E. K.). R. K. is the recipient of a fellowship of the Foundation for Polish Science.