Parallel synthesis and nucleic acid binding properties of C(6')-[alpha]-functionalized bicyclo-DNA

Silhár, Peter; Leumann, Christian J. (2010). Parallel synthesis and nucleic acid binding properties of C(6')-[alpha]-functionalized bicyclo-DNA. Bioorganic & medicinal chemistry, 18(22), pp. 7786-7793. Amsterdam: Elsevier 10.1016/j.bmc.2010.09.064

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Two novel bicyclo-T nucleosides carrying a hydroxyl or a carboxymethyl substituent in C(6')-[alpha]-position were prepared and incorporated into oligodeoxynucleotides. During oligonucleotide deprotection the carboxymethyl substituent was converted into different amide substituents in a parallel way. Tm-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.

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