PNA Molecular Beacons Assembled by Post‐Synthetic Click Chemistry Functionalization. Issue 15 (3rd September 2015)

• Record Type: Journal Article
• Authors: Wang, Xiaoxiao; Hudson, Robert H. E.
• Is Part Of: Chembiochem. Volume 16:Issue 15(2015)
• Page Start: 2156
• Page End: 2161
• Publication Date: 2015-09-03
• Subjects: Biochemistry -- Periodicals; Molecular biology -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1002/cbic.201500248
• Languages: English
• ISSNs: 1439-4227

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>To avoid the tedious synthesis of functionalized peptide nucleic acid (PNA) monomers for probe development, we proposed a simple approach to modify PNA oligomers by post‐synthetic on‐resin click chemistry. PNA molecular beacons (MBs) were prepared by incorporation of azide‐containing monomers into the oligomer by automatic solid‐phase peptide synthesis and subsequent derivatization with pyrene moieties by copper‐catalyzed azide–alkyne cycloaddition. Two pyrene‐based quencher‐free PNA molecular beacons, a stemless MB and one possessing a stem–loop structure, targeting a portion of the cystic fibrosis gene, were successfully synthesized by using this method. Fluorescence studies showed that the stem–loop MB exhibited better discrimination of changes in excimer/monomer ratios as compared to the stemless MB construct.</p> </abstract>