Tricyclic Nucleobase Analogs and Their Ribosides as Substrates and Inhibitors of Purine-Nucleoside Phosphorylases III. Aminopurine Derivatives.

ABSTRACT: Etheno-derivatives of 2-aminopurine, 2-aminopurine riboside, and 7-deazaadenosine (tubercidine) were prepared and purified using standard methods. 2-Aminopurine reacted with aqueous chloroacetaldehyde to give two products, both exhibiting substrate activity towards bacterial (E. coli) purine-nucleoside phosphorylase (PNP) in the reverse (synthetic) pathway. The major product of the chemical synthesis, identified as 1,N²-etheno-2-aminopurine, reacted slowly, while the second, minor, but highly fluorescent product, reacted rapidly. NMR analysis allowed identification of the minor product as N²,3-etheno-2-aminopurine, and its ribosylation product as N²,3-etheno-2-aminopurine-N²--D-riboside. Ribosylation of 1,N²-etheno-2-aminopurin

SUBMITTER: Stachelska-Wierzchowska A 

PROVIDER: S-EPMC7037862 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature