Title: Fluorescent 5-Pyrimidine and 8-Purine Nucleosides Modified with an N-Unsubstituted 1,2,3-Triazol-4-yl Moiety.
Authors: Wen, Zhiwei; Tuttle, Paloma R; Howlader, A Hasan; Vasilyeva, Anna; Gonzalez, Laura; Tangar, Antonija; Lei, Ruipeng; Laverde, Eduardo E; Liu, Yuan; Miksovska, Jaroslava; Wnuk, Stanislaw F
Published In J Org Chem, (2019 03 15)
Abstract: The Cu(I)- or Ag(I)-catalyzed cycloaddition between 8-ethynyladenine or guanine nucleosides and TMSN3 gave 8-(1- H-1,2,3-triazol-4-yl) nucleosides in good yields. On the other hand, reactions of 5-ethynyluracil or cytosine nucleosides with TMSN3 led to the chemoselective formation of triazoles via Cu(I)-catalyzed cycloaddition or vinyl azides via Ag(I)-catalyzed hydroazidation. These nucleosides with a minimalistic triazolyl modification showed excellent fluorescent properties with 8-(1- H-1,2,3-triazol-4-yl)-2'-deoxyadenosine (8-TrzdA), exhibiting a quantum yield of 44%. The 8-TrzdA 5'-triphosphate was incorporated into duplex DNA containing a one-nucleotide gap by DNA polymerase β.
PubMed ID: 30806513
MeSH Terms: Catalysis; Copper/chemistry; Fluorescence*; Molecular Structure; Purine Nucleosides/chemical synthesis; Purine Nucleosides/chemistry*; Pyrimidine Nucleosides/chemical synthesis; Pyrimidine Nucleosides/chemistry*; Silver/chemistry; Triazoles/chemistry*