Synthesis of 6'-branched locked nucleic acid by a radical TEMPO-scavanged stereoselective mercury cyclization.
A 6'(R)-hydroxymethyl derivative of the locked nucleic acid (LNA)-thymidine monomer has been synthesized by a stereoselective mercury cyclization and subsequent use of TEMPO as a radical scavenger. This compound was converted to an azide derivative, which in a Huisgen-type [3 + 2] cycloaddition afforded a double-headed nucleoside with a triazole linking an additional thymine to the 6'-position of the LNA-nucleoside monomer.
Enderlin
Gerald
G
Nucleic Acid Center, Department of Physics and Chemistry, University of Southern Denmark, 5230 Odense M, Denmark.
Nielsen
Poul
P
D001386:Azides / Q000737:chemistry; D003497:Cyclic N-Oxides / Q000737:chemistry*; D003500:Cyclization; D016166:Free Radical Scavengers / Q000737:chemistry*; D008628:Mercury / Q000737:chemistry*; D008956:Models, Chemical; D009841:Oligonucleotides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013936:Thymidine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D014230:Triazoles / Q000737:chemistry
D001386:Azides; D003497:Cyclic N-Oxides; D016166:Free Radical Scavengers; D009841:Oligonucleotides; D014230:Triazoles; C477371:locked nucleic acid; D008628:Mercury; D013936:Thymidine; C003959:TEMPO