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Nucleotides. Part LXXII
Author(s) -
Beier Markus,
Pfleiderer Wolfgang
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390205
Subject(s) - chemistry , diazomethane , methylation , nucleotide , nucleic acid , stereochemistry , transfer rna , sulfonyl , combinatorial chemistry , rna , organic chemistry , biochemistry , dna , alkyl , gene
The synthesis of various N ‐methylated nucleosides (m 6 A, m 3 C, m 4 C, m 3 U) is described. These minor nucleosides can be obtained by simple methylation with diazomethane of [2‐(4‐nitrophenyl)ethoxy]carbonyl(npeoc)‐protected nucleosides. These methylated compounds are easily further derivatized to fit into the scheme of the [2‐(dansyl)ethoxy]carbonyl (dnseoc) approach for RNA synthesis (dansyl=[5‐(dimethylamino)naphthalen‐1‐yl]sulfonyl). Various oligoribonucleotides containing N 6 ‐methyladenosine were synthesized, underlining the usefulness of the dnseoc approach, especially for the synthesis of natural tRNA‐derived oligoribonucleotide sequences.