Abstract
In this work, we report the asymmetric synthesis and characterization of an artificial amino acid based on triazolyl-thione L-alanine, which was modified with a thiophenyl-substituted moiety, as well as in vitro studies of its nucleic acid-binding ability. We found, by dynamic light scattering studies, that the synthetic amino acid was able to form supramolecular aggregates having a hydrodynamic diameter higher than 200 nm. Furthermore, we demonstrated, by UV and CD experiments, that the heteroaromatic amino acid, whose enzymatic stability was demonstrated by HPLC analysis also after 24 h of incubation in human serum, was able to bind a RNA complex, which is a feature of biomedical interest in view of innovative antiviral strategies based on modulation of RNA-RNA molecular recognition.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Alanine / analogs & derivatives*
-
Alanine / chemical synthesis
-
Alanine / chemistry
-
Alanine / metabolism
-
Amino Acids, Aromatic / chemical synthesis*
-
Amino Acids, Aromatic / chemistry
-
Amino Acids, Aromatic / metabolism
-
Antiviral Agents / chemical synthesis*
-
Antiviral Agents / chemistry
-
Antiviral Agents / metabolism
-
Circular Dichroism
-
Drug Design*
-
Magnetic Resonance Spectroscopy
-
Molecular Conformation
-
Molecular Structure
-
Nephelometry and Turbidimetry
-
RNA / chemistry
-
RNA / metabolism
-
Spectrometry, Mass, Electrospray Ionization
-
Spectrophotometry, Ultraviolet
-
Thiophenes / chemical synthesis
-
Thiophenes / chemistry*
-
Thiophenes / metabolism
-
Triazoles / chemical synthesis
-
Triazoles / chemistry*
-
Triazoles / metabolism
Substances
-
Amino Acids, Aromatic
-
Antiviral Agents
-
Thiophenes
-
Triazoles
-
RNA
-
Alanine