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

Włodzimierz J. Krzyżosiak | Zendy; Jan F. Biernat | Zendy; Jerzy Ciesiołka | Zendy; P. Gónicki | Zendy; M. WiewióSrowski | Zendy

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

Author(s) -

Włodzimierz J. Krzyżosiak,

Jan F. Biernat,

Jerzy Ciesiołka,

P. Gónicki,

M. WiewióSrowski

Publication year - 1979

Publication title -

nucleic acids research

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 9.008

H-Index - 537

eISSN - 1362-4954

pISSN - 0305-1048

DOI - 10.1093/nar/7.6.1663

Subject(s) - carbodiimide , chemical modification , aniline , amine gas treating , glycine , ethylenediamine , adenosine , reactivity (psychology) , medicinal chemistry , chemical structure , stereochemistry , adenosine monophosphate , chemistry , organic chemistry , amino acid , polymer chemistry , biochemistry , medicine , alternative medicine , pathology

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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