期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 24, 期 7, 页码 1544-1553出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201704338
关键词
backbone modifications; DNA; oligonucleotides; peptides; stereoselective synthesis
资金
- Deutsche Forschungsgemeinschaft (DFG) [DU 1095/2-1]
- Deutsche Forschungsgemeinschaft (Emmy Noether program) [GR 3592/2-1]
- Fonds der Chemischen Industrie (FCI, Sachkostenzuschuss)
- Studienstiftung des deutschen Volkes
- AstraZeneca
- Bayer CropScience
- Bayer HealthCare
- Boehringer Ingelheim
- Merck KGaA
- Max Planck Society
Non-natural oligonucleotides represent important (bio) chemical tools and potential therapeutic agents. Backbone modifications altering hybridization properties and biostability can provide useful analogues. Here, we employ an artificial nucleosyl amino acid (NAA) motif for the synthesis of oligonucleotides containing a backbone decorated with primary amines. An oligo-T sequence of this cationic DNA analogue shows significantly increased affinity for complementary DNA. Notably, hybridization with DNA is still gov-erned by Watson-Crick base pairing. However, single base pair mismatches are tolerated and some degree of sequence-independent interactions between the cationic NAA backbone and fully mismatched DNA are observed. These findings demonstrate that a high density of positive charges directly connected to the oligonucleotide backbone can affect Watson-Crick base pairing. This provides a paradigm for the design of therapeutic oligonucleotides with altered backbone charge patterns.
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