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

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Publication date 2010
Author Silhár Peter, Leumann Christian J.,
Project Chemically modified Oligonucleotides for Biotechnology and Material Sciences
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Original article (peer-reviewed)

Journal Bioorganic & Medicinal Chemistry
Volume (Issue) 18
Page(s) 7786 - 7793
Title of proceedings Bioorganic & Medicinal Chemistry


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.