The spontaneous rearrangement of 2,4-dinitrophenyl substituent in ribonucleosides under neutral conditions.
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.
Olejnik
Anna
A
Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznan, Poland.
Gdaniec
Zofia
Z
Kierzek
Elzbieta
E
Kierzek
Ryszard
R
D019297:2,4-Dinitrophenol / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D009843:Oligoribonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D012263:Ribonucleosides / Q000737:chemistry*
D009843:Oligoribonucleotides; D012263:Ribonucleosides; D019297:2,4-Dinitrophenol