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Trichogin is a natural peptide endowed with antimicrobial and antitumor activity. A member of the peptaibol family, trichogin possesses a C-terminal aminoalcohol. In the past, we substituted that moiety with a methyl ester for synthetic purposes and realized that this apparently slight modification causes great changes in the peptide bioactivity. Aiming at understanding the reasons behind such observations, we performed a detailed spectroscopic study on a number of trichogin analogs. In the present manuscript, we compare the data obtained from synchrotron radiation circular dichroism, NMR and fluorescence spectroscopy in organic solvents at cryogenic temperatures with those independently acquired by electron paramagnetic resonance spectroscopy at 80K. We reveal unambiguously the presence of a reversible, temperature-driven screw-sense interconversion from right-handed to left-handed helix that is determined by the C-terminal capping moiety. Our data demonstrate for the first time the key role of a C-terminal methyl ester in promoting peptide screw-sense inversion.
This article was published in the following journal.
Name: Chembiochem : a European journal of chemical biology
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Analogs of RNA cap compounds which do not have a positive charge. These compounds inhibit the initiation of translation of both capped and uncapped messenger RNA.
Measurement of the temperature of a material, or of the body or an organ by various temperature sensing devices which measure changes in properties of the material that vary with temperature, such as ELASTICITY; MAGNETIC FIELDS; or LUMINESCENCE.
A highly abundant DNA binding protein whose expression is strongly correlated with the growth phase of bacteria. The protein plays a role in regulating DNA topology and activation of RIBOSOMAL RNA transcription. It was originally identified as a factor required for inversion stimulation by the Hin recombinase of SALMONELLA and Gin site-specific recombinase of BACTERIOPHAGE MU.
Analogs of those substrates or compounds which bind naturally at the active sites of proteins, enzymes, antibodies, steroids, or physiological receptors. These analogs form a stable covalent bond at the binding site, thereby acting as inhibitors of the proteins or steroids.
The temperature at which a substance changes from one state or conformation of matter to another.