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

Grant number: 19/22319-5
Support Opportunities: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
Host Institution: Instituto de Ciência e Tecnologia (ICT). Universidade Federal de São Paulo (UNIFESP). Campus São José dos Campos. São José dos Campos , SP, Brazil
Associated 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)

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Scientific publications (14)
(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)
BATISTA, ANDREA N. L.; ANGRISANI, BIANCA R. P.; LIMA, MARIA EMANUELLE D.; DA SILVA, STEPHANIE M. P.; SCHETTINI, VITORIA H.; CHAGAS, HIGOR A.; DOS SANTOS, JR., FERNANDO M.; BATISTA, JR., JOAO M.; VALVERDE, ALESSANDRA L.. Absolute Configuration Reassignment of Natural Products: An Overview of the Last Decade. Journal of the Brazilian Chemical Society, v. 32, n. 8, p. 1499-1518, . (19/22319-5)
BATISTA, ANDREA N. L.; SANTOS, CARLOS HENRIQUE T.; DE ALBUQUERQUE, ANA CAROLINA F.; SANTOS JR, FERNANDO M.; GARCEZ, FERNANDA R.; BATISTA JR, JOAO M.. Absolute configuration reassignment of nectamazin A: Implications to related neolignans. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, v. 304, p. 6-pg., . (19/22319-5)
BOGAERTS, JONATHAN; AERTS, ROY; VERMEYEN, TOM; JOHANNESSEN, CHRISTIAN; HERREBOUT, WOUTER; BATISTA, JOAO M.. Tackling Stereochemistry in Drug Molecules with Vibrational Optical Activity. PHARMACEUTICALS, v. 14, n. 9, . (19/22319-5)
WIETHAN, CARSON; BRAGA, INGREDY B.; MENEZES DA SILVA, VITOR H.; BATISTA JR, JOAO M.; CORREIA, CARLOS ROQUE D.. Enantioselective Synthesis of Isoindolones via Palladium - Catalyzed Intramolecular Heck-Mizoroki Reactions of Endocyclic Enamides Using N,N-Ligands. CHEMCATCHEM, v. N/A, p. 7-pg., . (13/07600-3, 19/22319-5, 17/18207-1, 18/08627-6, 14/25770-6)
MONTEIRO, JACKSON; PASSERO, LUIZ FELIPE D.; JESUS, JESSICA A.; LAURENTI, MARCIA D.; LAGO, JOAO H. G.; SOARES, MARISI G.; BATISTA, ANDREA N. L.; BATISTA JR, JOAO M.; SARTORELLI, PATRICIA. Absolute Configuration and Antileishmanial Activity of (-)-Cyclocolorenone Isolated from Duguetia lanceolata (Annonaceae). CURRENT TOPICS IN MEDICINAL CHEMISTRY, v. 22, n. 19, p. 8-pg., . (18/24077-6, 21/02789-7, 19/22319-5, 16/24985-4)
YOKOMICHI, MARIA A. S.; SILVA, HANYENY R. L.; BRANDAO, LORENZA E. V. N.; VICENTE, EDUARDO F.; BATISTA JR, JOAO M.. onformational preferences induced by cyclization in orbitides: a vibrational CD stud. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 20, n. 6, p. 1306-1314, . (19/22319-5, 16/00446-7)
DE OLIVEIRA, VALDEIR C.; ANGNES, RICARDO A.; BATISTA JR, JOAO M.; CORREIA, CARLOS ROQUE D.. Diastereoselective and Enantioselective Heck Alkenylation of Cyclopent-3-en-1-ylmethanol with Alkenyl Triflates and Evaluation of Noncovalent Effects. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. N/A, p. 9-pg., . (13/07600-3, 14/25770-6, 19/22319-5)
BATISTA, JOAO M.; NICU, VALENTIN PAUL. Simplified and enhanced VCD analysis of cyclic peptides guided by artificial intelligence. Physical Chemistry Chemical Physics, v. 25, n. 33, p. 6-pg., . (19/22319-5)
GUBIANI, JULIANA R.; BERNARDI, DARLON I.; DE PAULA, CAIO C. P.; SELEGHIM, MIRNA H. R.; FERREIRA, ANTONIO G.; BATISTA, ANDREA N. L.; BATISTA, JOAO M.; OLIVEIRA, LUCIANNE F. P.; LIRA, SIMONE P.; BURDETTE, JOANNA E.; et al. Absolute configuration of cytotoxic anthraquinones from a Brazilian cave soil-derived fungus, Aspergillus sp. SDC28. ARCHIV DER PHARMAZIE, v. 355, n. 4, p. 8-pg., . (17/12436-9, 17/06014-4, 19/17721-9, 19/22319-5, 13/50228-8, 16/21341-9)
BATISTA, ANDREA N. L.; DOS SANTOS JR, FERNANDO M.; VALVERDE, ALESSANDRA L.; BATISTA JR, JOAO M.. Vibrational Circular Dichroism for the Assignment of Absolute Configuration of Natural Products in Brazil. REVISTA BRASILEIRA DE FARMACOGNOSIA-BRAZILIAN JOURNAL OF PHARMACOGNOSY, v. 31, n. 5, . (19/22319-5)
PINTO, BRYAN N. S.; ALVARENGA, ELSON S.; SANTOS, ANDERSON R.; OLIVEIRA, WASHINGTON F.; DE PAULA, VANDERLUCIA F.; OLIVEIRA, MARCIO N.; JUNIOR, JOAO M. B.; BATISTA, ANDREA N. DE L.. Structural Elucidation by NMR Analysis Assisted by DFT Calculations of a Novel Natural Product from Conchocarpus Mastigophorus (Rutaceae). ASIAN JOURNAL OF ORGANIC CHEMISTRY, v. 11, n. 6, p. 7-pg., . (19/22319-5)
VERMEYEN, TOM; BATISTA, ANDREA N. L.; VALVERDE, ALESSANDRA L.; HERREBOUT, WOUTER; BATISTA JR, JOAO M.. Pushing the boundaries of VCD spectroscopy in natural product chemistry. Physical Chemistry Chemical Physics, v. 25, n. 20, p. 8-pg., . (19/22319-5)
DUARTE CHORRO, TOMAZ HENRIQUE; SCARPA DE SOUZA, EDSON LEONARDO; KOSTER, OTTO DAOLIO; POLO, ELLEN CHRISTINE; CARMONA, RAFAELA COSTA; MENEZES DA SILVA, VITOR HUGO; BATISTA JUNIOR, JOAO MARCOS; DUARTE CORREIA, CARLOS ROQUE. In Tandem Enantioselective Intramolecular Heck-Matsuda Reactions directly from Anilines. ADVANCED SYNTHESIS & CATALYSIS, v. 365, n. 2, p. 13-pg., . (13/07600-3, 18/16916-8, 19/25657-9, 19/22319-5, 14/25770-6, 18/00271-8, 17/18207-1, 18/02945-6)
BATISTA, ANDREA N. L.; BRITO, MATEUS F.; BATISTA JR, JOAO M.; VALVERDE, ALESSANDRA L.. Plakilactone J: Structure and absolute configuration. Tetrahedron Letters, v. 112, p. 4-pg., . (19/22319-5)

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