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Nucleic Acids Research, 1979, Vol. 7, No. 6 1663-1674
© 1979

Articles

Chemical modification of N6-(N-threonylcarbonyl) adenosine. Part II Condensation of the carboxyi group with amine

W.J. Krzyzosiak, J. Biernat, J. Ciesiolka, P. Gónicki and M. WiewióSrowski+

Department of Stereochemistry of Natural Products, Institute of Organic Chemistry, Polish Academy of Sciences Noskowskiego 12/14, 61-704 Poznan, Poland

+To whom all correspondence should be addressed

Received August 3, 1979. Carboxyl group of N6 -/N-threonylcarbonyl/adenosine was quantitatively modified with amines /aniline, glycine ethyl ester and ethylenediamine/ in the presence of a water-soluble carbodiimide, yielding the respective amides.The reaction was carried out in a water solution of pH about 4 at 20°C and was finished within minutes. The structure of the products was confirmed by UV and PMR spectra, and by chemical reactivity. Under conditions applied for modification of t6A, four common nucleo-sides and internucleotide linkage of UpA were unreactive, while 51-AMP was transformed to the respective phosphoramides. At pH 4, the rate of 5 1-AMP modification was over 100 times lower than the rate of t6A reaction.


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