Ribozymomimetic Chemical Synthesis of Peptide Bond Using Phosphorous Acid/Oxirane Mediators

Abstract

A model system is created that mimics natural ribosome as well as the way of ribozyme action. It uses oxirane analogue as condensation reagent and H₃PO₃ as activator for the carboxyl group and as protecting reagent for the NH₂ function. In order to demonstrate the ability of the H₃PO₃/oxirane system to mimic natural peptide bond synthesis on the ribosome as well as to mimic the ribozyme synthesis and hydrolysis of an inter biomonomeric bond, four model compounds containing an amide bond were synthesized using phosphorous acid/oxirane mediators.

GRAPHICAL ABSTRACT

Keywords:

• Cyclic phospholanes
• oxirane
• peptide synthesis
• H-phosphonates
• ribozymomimetic
• vicinal hydroxyl group

Acknowledgements

The financial support by the National Research Fund of Bulgaria for the purchase of a Bruker Avance II+ 600 NMR spectrometer in the framework of the Program “Promotion of the Research Potential through Unique Scientific Equipment” (Project UNA-17/2005) and the COST action CM0802 ‘‘PhoSciNet” is gratefully acknowledged.