Planning and obtaining of Pohlianin A analog orbitids using D and L-amino acids for conformational studies via Vibrational Circular Dichroism (VCD)

• Grant number: 22/10961-7
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date until: November 01, 2022
• End date until: October 31, 2023
• Field of knowledge: Biological Sciences - Biochemistry - Chemistry of Macromolecules
• Principal Investigator: Eduardo Festozo Vicente
• Grantee: Gabriel da Silva Teodoro
• Host Institution: Faculdade de Ciências e Engenharia. Universidade Estadual Paulista (UNESP). Campus de Tupã. Tupã , SP, Brazil

Abstract

Studies on the cyclic peptides structures have been advancing significantly, and may help in several areas of scientific research. Specifically, the cyclic peptide Pohlianina A, belonging to the Jatropha genus and classified as an orbitid, fits into the area of natural products with promising biological activities. Thus, in order to analyze different conformations of this molecule and obtain a better understanding of its structure, in this project, analogs of Pohlianin A will be developed containing substitutions of naturally occurring L-amino acids by their D-enantiomers, allowing the possibility to observe their different structuring and three-dimensional constraints in different solvents, using the VCD technique (Vibrational Circular Dichroism). The designed orbitides analogs to Pohlianin A will be obtained via solid phase peptide synthesis, purified via high performance liquid chromatography (HPLC) and characterized via mass spectrometry. The analyzes of the synthesized cyclic peptides analogs to Pohlianin A will be carried out by means of VCD spectroscopy, in order to analyze the conformational restrictions that will result from the modifications from specific orbitide motifs with the D-amino acids. This project is a continuation of the studies that were carried out with D and L orbitids of Pohlianin A, in which the first successful spectroscopic studies were carried out. Thus, the project also aims to contribute to the creation and expansion of a spectral library of VCD for peptides, cyclic and linear, containing L and D amino acids, in order to identify markers for their conformations/configurations to be used in future studies of relationship. biological structure-activity for orbitids.