Abstract
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 degrees 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 nucleosides and internucleotide linkage of UpA were unreactive, while 5'-AMP was transformed to the respective phosphoramides. At pH 4, the rate of 5'-AMP modification was over 100 times lower than the rate of t6A reaction.
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Selected References
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- Hoare D. G., Koshland D. E., Jr A method for the quantitative modification and estimation of carboxylic acid groups in proteins. J Biol Chem. 1967 May 25;242(10):2447–2453. [PubMed] [Google Scholar]
- Hong C. I., Chheda G. B., Dutta S. P., O'Grady-Curtis A., Tritsch G. L. Synthesis and biological activity of analogs of naturally occurring 6-ureidopurines and their nucleosides. J Med Chem. 1973 Feb;16(2):139–147. doi: 10.1021/jm00260a013. [DOI] [PubMed] [Google Scholar]
- Miller J. P., Hussain Z., Schweizer M. P. The involvement of the anticodon adjacent modified nucleoside N-(9-(BETA-D-ribofuranosyl) purine-6-ylcarbamoyl)-threonine in the biological function of E. coli tRNAile. Nucleic Acids Res. 1976 May;3(5):1185–1201. doi: 10.1093/nar/3.5.1185. [DOI] [PMC free article] [PubMed] [Google Scholar]