Open AccessChemical synthesis of 5-azacytidlne nucleotides and preparation of tRNAs containing 5-azacytidine in its 3′-terminus
Author(s) -
Wojciech S. Zidinski,
Mathias Sprinzl
Publication year - 1984
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/12.12.5025
Subject(s) - polynucleotide , biology , biochemistry , nucleotide , transfer rna , ribosome , yeast , transferase , hydrolysis , peptidyl transferase , triazine , phosphate , substrate (aquarium) , dna , stereochemistry , enzyme , rna , chemistry , ecology , polymer chemistry , gene
5-azacytidine-5'-triphosphate prepared from 5-azacytidine by chemical phosphorylation is a substrate for AMP (CMP) tRNA nucleotidyl transferase from yeast. tRNAsPhe from yeast containing 5-azacytidine in their 3'-termini were prepared enzymatically. tRNAPhe-Cpn5CpA and tRNAPhe-n5Cpn5CpA can be aminoacylated by phenylalanyl-tRNA synthetase from yeast and they are active in the poly(U)-dependent synthesis of poly(Phe) on E. coli ribosomes. The decomposition of 5-azacytidine via hydrolysis of the triazine ring is significantly accelerated by a phosphate group on the 5'-position of the nucleotide. After the incorporation of 5-azacytidine-5'-phosphate into a polynucleotide chain the rate of hydrolysis of the triazine ring decreases considerably.