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Vibrational circular dichroism spectral markers: facilitating absolute configuration assignment of natural products

Grant number: 19/22319-5
Support type:Regular Research Grants
Duration: November 01, 2020 - October 31, 2022
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:João Marcos Batista Junior
Grantee:João Marcos Batista Junior
Home Institution: Instituto de Ciência e Tecnologia (ICT). Universidade Federal de São Paulo (UNIFESP). Campus São José dos Campos. São José dos Campos , SP, Brazil
Assoc. researchers: Patrick Bultinck ; Wouter Alfons Herrebout


Chirality is ubiquitous in nature and is a cornerstone of life itself. On a molecular level it is reflected in the fascinating structural complexity of many secondary metabolites. Over the years, nature-derived and/or inspired compounds have been playing a major role in drug discovery and development processes, as they are intrinsically endowed with the structural and stereochemical requirements to interact with protein receptors. An important bottleneck in the natural product characterization pipeline, however, is the determination of absolute configurations. Vibrational optical activity methods, which combine the wealth of structural information inherent to vibrational spectroscopy with sensitivity to chirality, have emerged as powerful tools in the natural product chemist's toolbox. However, the requirement of quantum chemical computations to interpret experimental data has precluded the use of vibrational circular dichroism, Raman optical activity as well as other chiroptical methods by non-experts. Therefore, in the present project we propose an extensive chiroptical investigation of representative terpenes, alkaloids, and cyclic peptides, in order to experimentally identify and validate spectral markers to be used in the stereochemical assignment of structurally related molecules. By combining the expertise of the research groups in São Paulo State and in Flanders we will build a chiroptical spectral library of natural products that will greatly assist other researchers in the field. Each spectral marker identified will be validated by quantum mechanical calculations and, with the use of modern chemometric and machine learning tools, will allow stereochemical characterization even in complex mixtures, such as crude extracts. (AU)