Parallel synthesis and nucleic acid binding properties of C(6')-α-functionalized bicyclo-DNA.
Two novel bicyclo-T nucleosides carrying a hydroxyl or a carboxymethyl substituent in C(6')-α-position were prepared and incorporated into oligodeoxynucleotides. During oligonucleotide deprotection the carboxymethyl substituent was converted into different amide substituents in a parallel way. T(m)-measurements showed no dramatic differences in both, thermal affinity and mismatch discrimination, compared to unmodified oligonucleotides. The post-synthetic modification of the carboxymethyl substituent allows in principle for a parallel preparation of a library of oligonucleotides carrying diverse substituents at C(6'). In addition, functional groups can be placed into unique positions in a DNA double helix.
Silhár
Peter
P
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
Leumann
Christian J
CJ
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D044366:Transition Temperature
D001643:Bridged Bicyclo Compounds; D009705:Nucleosides; D009838:Oligodeoxyribonucleotides