Synthesis of Biologically Active Peptide Nucleic Acid−Peptide Conjugates by Sortase-Mediated Ligation
| Autor: | Jana Klose, Oliver Kraetke, Yvonne Wolf, Stephan Pritz, Michael Beyermann, Michael Bienert |
|---|---|
| Rok vydání: | 2007 |
| Předmět: |
chemistry.chemical_classification
Peptide nucleic acid Stereochemistry Molecular Sequence Data Organic Chemistry Peptide Aminoacyltransferases Chemical synthesis Cysteine Endopeptidases chemistry.chemical_compound Bacterial Proteins chemistry Biochemistry Sortase Nucleic Acids Sortase A Nucleic acid Amino Acid Sequence Chemical ligation Peptides Peptide sequence |
| Zdroj: | The Journal of Organic Chemistry. 72:3909-3912 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo062331l |
| Popis: | Sortase A is a transpeptidase that cleaves at a pentapeptide-motif and subsequently transfers the acyl component to a nucleophile containing N-terminal oligoglycines. We investigate the reaction conditions of the sortase-mediated ligation and demonstrate a useful application by the synthesis of a peptide nucleic acid-cell-penetrating peptide chimera, the reaction equilibrium of which can be shifted in favor of the product by dialyzing out the low molecular weight byproduct. The synthesized conjugate exhibits dose-dependent antisense activity. |
| Databáze: | OpenAIRE |
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