A new synthetic pathway to adenine-2-d, 9-alkyladenine-2-d, adenosine-2-d, and 2'-deoxyadenosine-2-d.
Unambiguous assignments of the purine ring protons in the NMR spectra of adenine (Ia) and its 9-substituted derivatives (Ib-f) have been made by comparison with those of the isotopically labeled adenines VIIIa-f. 9-Alkyl-2-deuterioadenines (VIIIb-d), adenosine-2-d (VIIIe), and 2'-deoxyadenosine-2-d (VIIIf) were synthesized from the 9-substituted adenines Ib-f through cyclization of the monocyclic intermediates VIb-f with formic acid-d2 or 1-(formyl-d)-2(1H)-pyridone. Hydrolysis of VIIIe with 0.5 N aq. HCl gave adenine-2-d (VIIIa) in 77% yield.
D000225:Adenine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D000241:Adenosine / Q000138:chemical synthesis*; D003839:Deoxyadenosines / Q000138:chemical synthesis*; D003903:Deuterium; D007202:Indicators and Reagents; D007553:Isotope Labeling / Q000379:methods
D003839:Deoxyadenosines; D007202:Indicators and Reagents; C001172:9-ethyladenine; C013115:9-methyladenine; D003903:Deuterium; D000225:Adenine; D000241:Adenosine