Uncharged stereoregular nucleic acid analogs: 2. Morpholino nucleoside oligomers with carbamate internucleoside linkages.
A novel oligonucleotide analog has been prepared from ribonucleoside derived morpholine subunits linked by carbamate groups. Oxidative cleavage of the 2',3' vicinal diol of cytidine followed by reductive amination of the resulting dialdehyde afforded the morpholine subunit. Coupling of the subunits are through carbamate moieties and the oligomers were characterized by 1H NMR and FAB MS. Evidence for interaction of the hexamer 19 with p(dG6) was found, but an atypical interaction of 19 with a RNA target was observed.
Stirchak
E P
EP
Antivirals, Inc., Corvallis, OR 97333.
Summerton
J E
JE
Weller
D D
DD
D002219:Carbamates; D055598:Chemical Phenomena; D002621:Chemistry; D002845:Chromatography; D006358:Hot Temperature; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis*; D009691:Nucleic Acid Denaturation; D009841:Oligonucleotides / Q000138:chemical synthesis*; D012995:Solubility
D002219:Carbamates; D009025:Morpholines; D009841:Oligonucleotides