Cross-Linked DNA Generated by "Bis-click" Reactions with Bis-functional Azides: Site Independent Ligation of Oligonucleotides via Nucleobase Alkynyl Chains.
Summary of "Cross-Linked DNA Generated by "Bis-click" Reactions with Bis-functional Azides: Site Independent Ligation of Oligonucleotides via Nucleobase Alkynyl Chains."
Template-free cross-linking of single-stranded DNA bearing octadiynyl side chains at the 7-position of 8-aza-7-deazapurine moieties with bisfunctional azides is reported employing a Cu(I)-catalyzed azide-alkyne "bis-click" reaction. Bis-adducts were formed when the bis-azide:oligonucleotide ratio was 1:1; monofunctionalization occurred when the ratio was 15:1. Four-stranded DNA consisting of two cross-linked duplexes was obtained after hydridization. Cross-linked duplexes are as stable as individual duplexes when ligation was introduced at terminal positions; ligation at a central position led to a slight duplex destabilization.
Affiliation
Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, 48149 Münster, Germany, and Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastrass
Journal Details
This article was published in the following journal.
Name: The Journal of organic chemistry
ISSN: 1520-6904
Pages: 8693-6
Links
- PubMed Source: http://www.ncbi.nlm.nih.gov/pubmed/21070038
- DOI: http://dx.doi.org/10.1021/jo101809w
Medical and Biotech [MESH] Definitions
Click Chemistry
Organic chemistry methodology that mimics the modular nature of various biosynthetic processes. It uses highly reliable and selective reactions designed to "click" i.e., rapidly join small modular units together in high yield, without offensive byproducts. In combination with COMBINATORIAL CHEMISTRY TECHNIQUES, it is used for the synthesis of new compounds and combinatorial libraries.
Cross Reactions
Serological reactions in which an antiserum against one antigen reacts with a non-identical but closely related antigen.
Evoked Potentials, Auditory, Brain Stem
Electrical waves in the CEREBRAL CORTEX generated by BRAIN STEM structures in response to auditory click stimuli. These are found to be abnormal in many patients with CEREBELLOPONTINE ANGLE lesions, MULTIPLE SCLEROSIS, or other DEMYELINATING DISEASES.
Immunologic Techniques
Techniques involving the demonstration or measurement of an immune response, including antibody production or assay, ANTIGEN-ANTIBODY REACTIONS, serologic cross-reactivity, DELAYED HYPERSENSITIVITY reactions, IMMUNIZATION, or heterogenetic responses.
Hydrogel
A network of cross-linked hydrophilic macromolecules used in biomedical applications.
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