Abstract
The hypermodified ureidonucleoside N6[((9-β-ᴅ-ribofuranosyl-9H-purine-6-yl)amino)carbonyl]- ʟ-threonine (5) is a constituent of transfer ribonucleic acid (tRNA) and is secreted as a tRNA catabolite in body fluids such as blood, milk and urine. Compound 5 and the isomeric ureidonucleosides bearing ᴅ-threonine (9), ʟ-allo- (7) and ᴅ-allo-threonine (11) as side chain moieties were synthesized on a preparative scale. The amido protons of 5 and 9 cause two separate 1H NMR signals whereas 7 and 11 cause multiplets. The 13C NMR signals of all carbon atoms of the allo-amino acid side chains (7, 11) are shifted downfield of the corresponding signals in compounds 5 and 9. The chemically protected intermediate compound adenosine urethane (3) is potentially of interest in the analysis of amino acids because it may be converted to nucleosides of the ureido type by reaction with amino acids in biological matrices.
Published Version (
Free)
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call