Synthesis and properties of spiro nucleosides containing the barbituric acid moiety.
The two chiral spiro nucleosides 4 and 5 containing the barbituric acid moiety were efficiently synthesized from optically pure precursors, and their properties were studied. The carbocyclic nucleoside 5 is considerably more stable against ring opening than the deoxyribosyl derivative 4. Both compounds present enhanced hydrogen bonding capacity with diacetyladenosine.
Renard
Annabelle
A
Chimie Bioorganique, L.E.D.S.S., Associé au CNRS, Université Joseph Fourier, BP 53, 38041 Grenoble Cedex 9, France.
Lhomme
Jean
J
Kotera
Mitsuharu
M
D001463:Barbiturates / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D001463:Barbiturates; D009705:Nucleosides; D013141:Spiro Compounds