Vibrational chiroptical spectroscopy for stereochemical characterization of small molecules and macromolecules

• Grant number: 14/25222-9
• Support Opportunities: Research Grants - Young Investigators Grants
• Start date: May 01, 2015
• End date: April 30, 2019
• 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
• City of the host institution: São José dos Campos
• Associated researchers: Laurence A. Nafie ; Maria Fátima das Graças Fernandes da Silva ; Quezia Bezerra Cass
• Associated scholarship(s): 15/07089-2 - Vibrational chiroptical spectroscopy for stereochemical characterization of small molecules and macromolecules, BP.JP

Abstract

Vibrational circular dichroism (VCD) and Raman optical activity (ROA), collectively know as vibrational optical activity (VOA), are powerful spectroscopic methods for the characterization of tridimensional structure of small molecules and macromolecules, as well as their interactions in solution. By combining the richness of spectral information from IR and Raman spectroscopies with sensitivity to chirality, VCD and ROA become excellent tools for determining the absolute configuration of small molecules and secondary structure of macromolecules. Despite their positive characteristics, both techniques are scantily used in Brazil. Therefore, the main goal of this project is to create the first VOA research group in the country in the Department of Chemistry at UFSCar, in order to determine the absolute configuration of natural and synthetic compounds, as well as to conduct systematic studies on the mechanisms of interaction between analytes and stationary phases used in classic chiral liquid chromatography and bioaffinity chromatography. This proposal is intended to combine the expertise of the proponent in VOA and quantum-chemical calculations with the demand for stereochemical analysis of two groups of excellence at UFSCar headed by Profs. Quezia B. Cass and Maria Fátima G. F. da Silva. Finally, this proposal aims to contribute to the development of high-quality human resources at UFSCar and also to boost the internationalization of São Paulo State research, since Prof. Laurence A. Nafie from Syracuse University, one of the world's leading researchers in the field will be part of the research team. (AU)

Scientific publications

(35)

(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)

CALISTO, ITALO H.; FURLAN, MAYSA; BLANCH, EWAN W.; BATISTA, JR., JOAO M.. Raman optical activity of a flavone C-diglycoside: Aqueous solution conformations and absolute configuration. VIBRATIONAL SPECTROSCOPY, v. 91, n. SI, p. 136-140, JUL 2017. (15/07089-2, 14/25222-9)

SCATENA, GABRIEL S.; CASSIANO, NEILA M.; NETTO, CHAQUIP D.; COSTA, PAULO R. R.; CASS, QUEZIA B.; BATISTA, JR., JOAO M.. Preparative chiral separation and absolute configuration of the synthetic pterocarpanquinone LQB-118. Chirality, v. 29, n. 5, p. 167-171, MAY 2017. (13/01710-1, 14/25222-9, 15/07089-2)

MARIACATERINA LIANZA; MARIA HELENA VERDAN; JEAN PAULO DE ANDRADE; FERRUCCIO POLI; LARISSA C. DE ALMEIDA; LETICIA V. COSTA-LOTUFO; ÁLVARO CUNHA NETO; SARAH C. C. OLIVEIRA; JAUME BASTIDA; ANDREA N. L. BATISTA; et al. Isolation, Absolute Configuration and Cytotoxic Activities of Alkaloids from Hippeastrum goianum (Ravenna) Meerow (Amaryllidaceae). Journal of the Brazilian Chemical Society, v. 31, n. 10, p. 2135-2145, 2020-10-09. (14/25222-9, 18/17595-0, 15/17177-6, 14/50926-0)

LONDERO, VINICIUS S.; COSTA-SILVA, THAIS A.; ANTAR, GUILHERME M.; BAITELLO, JOAO B.; DE OLIVEIRA, LARISSA V. F.; CAMILO, FERNANDA F.; BATISTA, ANDREA N. L.; BATISTA, JR., JOAO M.; TEMPONE, ANDRE G.; LAGO, JOAO HENRIQUE G.. Antitrypanosomal Lactones from Nectandra barbellata. Journal of Natural Products, v. 84, n. 5, p. 1489-1497, MAY 28 2021. (14/25222-9, 18/07885-1, 21/02789-7, 18/10279-6, 17/17044-1)

QUEIROZ, SUZANA APARECIDA S.; PINTO, MERI EMILI F.; BOBEY, ANTONIO F.; RUSSO, HELENA M.; BATISTA, ANDREA N. L.; BATISTA, JR., JOAO M.; CODO, ANA C.; MEDEIROS, ALEXANDRA I.; BOLZANI, VANDERLAN S.. Diterpenoids with inhibitory activity of nitrite production from Croton floribundus. Journal of Ethnopharmacology, v. 249, MAR 1 2020. (19/04381-5, 13/07600-3, 14/25222-9, 17/19870-6, 17/18807-9, 14/50926-0, 17/17098-4)

BATISTA, ANDREA N. L.; BATISTA, JR., JOAO M.; SOUZA-MOREIRA, TATIANA M.; VALENTINI, SANDRO R.; KATO, MASSUO J.; ZANELLI, CLESLEI F.; FURLAN, MAYSA. Biosynthetic Insights into p-Hydroxybenzoic Acid-Derived Benzopyrans in Piper gaudichaudianum. Journal of the Brazilian Chemical Society, v. 29, n. 5, p. 1105-1114, MAY 2018. (14/50316-7, 13/07600-3, 15/07089-2, 11/01003-8, 14/25222-9)

FRANCESCHINI SARRIA, ANDRE LUCIO; SILVA, TAYNARA LOPES; DE OLIVEIRA, JULIANA MAGALHAES; RODRIGUES DE OLIVEIRA, MILENE APARECIDA; FERNANDES, JOAO BATISTA; DAS GRACAS FERNANDES DA SILVA, MARIA FATIMA; VIEIRA, PAULO CEZAR; VENANCIO, TIAGO; ALVES FILHO, ELENILSON DE GODOY; BATISTA, JR., JOAO M.; et al. Dimeric chalcones derivatives from Myracrodruon urundeuva act as cathepsin V inhibitors. Phytochemistry, v. 154, p. 31-38, OCT 2018. (06/58043-3, 15/07089-2, 13/07600-3, 14/25222-9, 09/01847-1)

BATISTA, ANDREA N. L.; DOS SANTOS, JR., FERNANDO M.; VALVERDE, ALESSANDRA L.; BATISTA, JR., JOAO M.. Stereochemistry of spongosoritins: beyond optical rotation. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 17, n. 45, p. 9772-9777, DEC 7 2019. (14/25222-9)

SPRENGER, R. F.; THOMASI, S. S.; FERREIRA, A. G.; CASS, Q. B.; BATISTA JUNIOR, J. M.. Solution-state conformations of natural products from chiroptical spectroscopy: the case of isocorilagin. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 14, n. 13, p. 3369-3375, 2016. (11/11021-3, 13/01710-1, 14/25222-9, 15/07089-2)

GIMENES, LEILA; BATISTA JUNIOR, JOAO MARCOS; DOS SANTOS JUNIOR, FERNANDO MARTINS; SOUZA, MATHEUS DA SILVA; LUNA-DULCEY, LIANY; ELLENA, JAVIER ESTEVES; COMINETTI, MARCIA REGINA; DAS GRACAS FERNANDES DA SILVA, MARIA FATIMA; VIEIRA, PAULO CEZAR; FERNANDES, JOAO BATISTA; et al. Picraviane A and B: Nortriterpenes with limonoid-like skeletons containing a heptanolide E-ring system from Picramnia glazioviana. Phytochemistry, v. 163, p. 38-45, JUL 2019. (13/20458-1, 15/07089-2, 16/18024-1, 14/25222-9, 12/25299-6, 16/23794-0)

LIANZA, MARIACATERINA; VERDAN, MARIA HELENA; DE ANDRADE, JEAN PAULO; POLI, FERRUCCIO; DE ALMEIDA, LARISSA; COSTA-LOTUFO, LETICIA, V; CUNHA NETO, ALVARO; OLIVEIRA, SARAH C. C.; BASTIDA, JAUME; BATISTA, ANDREA N. L.; et al. Isolation, Absolute Configuration and Cytotoxic Activities of Alkaloids from Hippeastrum goianum (Ravenna) Meerow (Amaryllidaceae). Journal of the Brazilian Chemical Society, v. 31, n. 10, p. 11-pg., 2020-10-01. (18/17595-0, 15/17177-6, 14/50926-0, 14/25222-9)

PEREIRA CABRAL, MARCIA R.; CECCHETTO, MARIANA; BATISTA, JR., JOAO M.; BATISTA, ANDREA N. L.; FOGLIO, MARY ANN; TASCA GOIS RUIZ, ANA LUCIA; BARROTTO DO CARMO, MARTA R.; DA COSTA, WILLIAN FERREIRA; BALDOQUI, DEBORA C.; SARRAGIOTTO, MARIA H.. Cytotoxic sesquiterpene lactones from Campuloclinium macrocephalum (=Eupatorium macrocephalum). Phytochemistry, v. 179, NOV 2020. (14/25222-9)

DE AMORIM, MARCELO R.; WIJERATNE, E. M. KITHSIRI; ZHOU, SHENGLIANG; ARNOLD, A. ELIZABETH; BATISTA, ANDREA N. L.; BATISTA, JOAO M.; DOS SANTOS, LOURDES C.; GUNATILAKA, A. A. LESLIE. An epigenetic modifier induces production of 3-(4-oxopyrano)-chromen-2-ones in Aspergillus sp. AST0006, an endophytic fungus of Astragalus lentiginosus. Tetrahedron, v. 76, n. 43, OCT 23 2020. (18/05905-5, 14/25222-9)

KLEIN HENDGES, ANA PAULA P.; DOS SANTOS, ELAINE FERNANDA; TEIXEIRA, SIRLEI D.; SANTANA, FRANCIELLI S.; TREZZI, MICHELANGELO M.; BATISTA, ANDREA N. L.; BATISTA JR, JOAO M.; DE LIMA, VANDERLEI A.; MARQUES, FRANCISCO DE ASSIS; SALES MAIA, BEATRIZ HELENA L. N.. Phytotoxic Neocassane Diterpenes from Eragrostis plana. Journal of Natural Products, v. 83, n. 12, p. 3511-3518, DEC 24 2020. (14/25222-9)

SILVERIO, MAIRA R. S.; CALLEJON, DANIEL ROBERTO; BATISTA JR., JOAO M. BATISTA; RIUL, THALITA B.; DE OLIVEIRA, ANDERSON RODRIGO M. DE; LOPES, NORBERTO P.. In vitro Metabolism and Cytotoxicity of Parthenolide: The Complete Identification of the Major Oxidative Product and the Evaluation of Trypanocidal and Leishmanicidal Activities. Journal of the Brazilian Chemical Society, v. 36, n. 1, p. 8-pg., 2025-01-01. (16/07597-0, 14/25222-9, 18/07534-4)

ORTEGA, HUMBERTO E.; BATISTA, JR., JOAO M.; MELO, WEILAN G. P.; CLARDY, JON; PUPO, MONICA T.. Absolute configurations of griseorhodins A and C. Tetrahedron Letters, v. 58, n. 50, p. 4721-4723, DEC 13 2017. (15/07089-2, 14/25222-9, 15/01001-6, 13/50954-0)

DOS SANTOS, JR., FERNANDO M.; BICALHO, KEYLLA U.; CALISTO, ITALO H.; SCATENA, GABRIEL S.; FERNANDES, JOAO B.; CASS, QUEZIA B.; BATISTA, JR., JOAO M.. Scope of the 2(5H)-furanone helicity rule: a combined ECD, VCD, and DFT investigation. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 16, n. 24, p. 4509-4516, JUN 28 2018. (15/07089-2, 13/01710-1, 14/25222-9, 10/18832-4, 12/25299-6, 16/23794-0)

BATISTA, JR., JOAO M.; WANG, BO; CASTELLI, MARIA V.; BLANCH, EWAN W.; LOPEZ, SILVIA N.. Absolute configuration assignment of an unusual homoisoflavanone from Polygonum ferrugineum using a combination of chiroptical methods. Tetrahedron Letters, v. 56, n. 44, p. 6142-6144, OCT 28 2015. (14/25222-9, 15/07089-2)

BATISTA, ANDREA N. L.; DOS SANTOS, JR., FERNANDO M.; BATISTA, JR., JOAO M.; CASS, QUEZIA B.. Enantiomeric Mixtures in Natural Product Chemistry: Separation and Absolute Configuration Assignment. Molecules, v. 23, n. 2, FEB 2018. (13/01710-1, 16/23794-0, 14/25222-9, 15/07089-2)

RODRIGUES DE AMORIM, M.; WIJERATNE, E. M. K.; BATISTA JUNIOR, J. M.; DOS SANTOS, L. C.; GUNATILAKA, A. A. L.. An epigenetic modifier induces the production of new metabolites by Aspergillus terreus AST0006. Planta Medica, v. 85, n. 18, p. 1-pg., 2019-12-01. (18/05905-5, 15/11058-5, 14/25222-9)

DE AMORIM, MARCELO R.; HILARIO, FELIPE; DOS SANTOS JUNIOR, FERNANDO M.; BATISTA JUNIOR, JOAOM.; BAUAB, TAIS M.; ARAUJO, ANGELA R.; CARLOS, IRACILDA Z.; VILEGAS, WAGNER; DOS SANTOS, LOURDES C.. New Benzaldehyde and Benzopyran Compounds from the Endophytic Fungus Paraphaeosphaeria sp. F03 and Their Antimicrobial and Cytotoxic Activities {*}. Planta Medica, v. 85, n. 11/12, p. 957-964, AUG 2019. (14/25222-9, 16/23794-0, 15/04899-3, 15/11058-5)

MAÍRA R. S. SILVÉRIO; DANIEL ROBERTO CALLEJON; JOÃO M. BATISTA JR.; THALITA B. RIUL; ANDERSON RODRIGO M. DE OLIVEIRA; NORBERTO P. LOPES. In vitro Metabolism and Cytotoxicity of Parthenolide: The Complete Identification of the Major Oxidative Product and the Evaluation of Trypanocidal and Leishmanicidal Activities. Journal of the Brazilian Chemical Society, v. 36, n. 1, 2024-06-17. (16/07597-0, 14/25222-9, 18/07534-4)

CCANA-CCAPATINTA, GARI V.; SAMPAIO, BRUNO L.; DOS SANTOS, JR., FERNANDO M.; BATISTA, JR., JOAO M.; DA COSTA, FERNANDO B.. Absolute configuration assignment of caffeic acid ester derivatives from Tithonia diversifolia by vibrational circular dichroism: the pitfalls of deuteration. TETRAHEDRON-ASYMMETRY, v. 28, n. 12, p. 1823-1828, DEC 15 2017. (15/07089-2, 11/13361-6, 14/26866-7, 14/25222-9, 14/16850-6, 16/23794-0)

PASSARELI, F.; BATISTA, A. N. L.; CAVALHEIRO, A. J.; HERREBOUT, W. A.; BATISTA JUNIOR, J. M.. Vibrational spectroscopy as a direct stereochemical probe for polyhydroxylated molecules. Physical Chemistry Chemical Physics, v. 18, n. 45, p. 30903-30906, 2016. (14/25222-9, 15/07089-2)

BERNARDINO, K.; PINTO, M. E. F.; BOLZANI, V. S.; DE MOURA, A. F.; BATISTA JUNIOR, J. M.. Pinpointing disulfide connectivities in cysteine-rich proteins. CHEMICAL COMMUNICATIONS, v. 53, n. 53, p. 7337-7340, JUL 7 2017. (15/07089-2, 13/07600-3, 14/25222-9, 14/50304-9, 13/07296-2, 12/15147-4)

BATISTA, JR., JOAO M.; BLANCH, EWAN W.; BOLZANI, VANDERLAN DA SILVA. Recent advances in the use of vibrational chiroptical spectroscopic methods for stereochemical characterization of natural products. NATURAL PRODUCT REPORTS, v. 32, n. 9, p. 1280-1302, 2015. (11/22339-4, 13/07600-3, 14/25222-9, 14/50304-9)

ORTEGA, HUMBERTO E.; BATISTA, JR., JOAO M.; MELO, WEILAN G. P.; DE PAULA, GABRIELA T.; PUPO, MONICA T.. Structure and Absolute Configuration of Secondary Metabolites from Two Strains of Streptomyces chartreusis Associated with Attine Ants. Journal of the Brazilian Chemical Society, v. 30, n. 12, SI, p. 2672-2680, DEC 2019. (15/07089-2, 13/50954-0, 14/25222-9, 14/14095-6, 17/05920-1, 15/01001-6)

BATISTA, ANDREA N. L.; DOS SANTOS-PINTO, JOSE ROBERTO A.; BATISTA, JR., JOAO M.; SOUZA-MOREIRA, TATIANA M.; SANTONI, MARIANA M.; ZANELLI, CLESLEI F.; KATO, MASSUO J.; LOPEZ, SILVIA N.; PALMA, MARIO S.; FURLAN, MAYSA. The Combined Use of Proteomics and Transcriptomics Reveals a Complex Secondary Metabolite Network in Peperomia obtusifolia. Journal of Natural Products, v. 80, n. 5, p. 1275-1286, MAY 2017. (13/07600-3, 11/51684-1, 14/25222-9, 11/01003-8)

CALDAS, LHAIS ARAUJO; RODRIGUES, MARIANA T.; BATISTA, ANDREA N. L.; BATISTA, JR., JOAO M.; LAGO, JOAO H. G.; FERREIRA, MARCELO J. P.; RUBIO, ILEANA G. S.; SARTORELLI, PATRICIA. Sesquiterpene Lactones from Calea pinnatifida: Absolute Configuration and Structural Requirements for Antitumor Activity. Molecules, v. 25, n. 13, JUL 2020. (16/24985-4, 14/25222-9)

GUBIANI, JULIANA R.; OLIVEIRA, MICHELE C. S.; NEPONUCENO, RICARDO A. R.; CAMARGO, MARIA J.; GARCEZ, WALMIR S.; BIZ, ANDRESSA R.; SOARES, MARCOS A.; ARAUJO, ANGELA R.; BOLZANI, VANDERLAN DA S.; LISBOA, HELEN C. F.; et al. Cytotoxic prenylated indole alkaloid produced by the endophytic fungus Aspergillus terreus P63. PHYTOCHEMISTRY LETTERS, v. 32, p. 162-167, AUG 2019. (13/50228-8, 14/25222-9)

CANZI, EDIONE F.; DOS SANTOS, JR., FERNANDO M.; MENEGHETTI, EMANUELLE K.; SALES MAIA, BEATRIZ HELENA L. N.; BATISTA, JR., JOAO M.. Absolute configuration of a rare dibenzoylmethane derivative from Dahlstedtia glaziovii (Fabaceae). Tetrahedron Letters, v. 59, n. 2, p. 135-137, JAN 10 2018. (16/23794-0, 14/25222-9, 15/07089-2)

FERNANDEZ-BOBEY, ANTONIO; FERREIRA PINTO, MERI EMILI; DE ALMEIDA, LARISSA COSTA; DE SOUZA, BIBIANA MONSON; DIAS, NATHALIA BAPTISTA; DE PAULA-SOUZA, JULIANA; CILLI, EDUARDO MAFFUD; LOPES, NORBERTO PEPORINE; COSTA-LOTUFO, LETICIA VERAS; PALMA, MARIO SERGIO; et al. Cytotoxic Cyclotides from Anchietea pyrifolia, a South American Plant Species. Journal of Natural Products, v. 85, n. 9, p. 8-pg., 2022-08-31. (14/50926-0, 19/04381-5, 20/02207-5, 14/25222-9, 13/07600-3, 19/26550-3, 17/17098-4, 16/16212-5)

SCATENA, GABRIEL S.; CASSIANO, NEILA M.; NETTO, CHAQUIP D.; COSTA, PAULO R. R.; CASS, QUEZIA B.; BATISTA, JOAO M., JR.. Preparative chiral separation and absolute configuration of the synthetic pterocarpanquinone LQB-118. CHIRALITY, v. 29, n. 5, p. 5-pg., 2017-05-01. (13/01710-1, 14/25222-9, 15/07089-2)

CALISTO, ITALO H.; FURLAN, MAYSA; BLANCH, EWAN W.; BATISTA, JOAO M., JR.. Raman optical activity of a flavone C-diglycoside: Aqueous solution conformations and absolute configuration. VIBRATIONAL SPECTROSCOPY, v. 91, p. 5-pg., 2017-07-01. (14/25222-9, 15/07089-2)

DE AMORIM, MARCELO R.; HILARIO, FELIPE; DOS SANTOS JUNIOR, FERNANDO M.; BATISTA JUNIOR, JOAOM.; BAUAB, TAIS M.; ARAUJO, ANGELA R.; CARLOS, IRACILDA Z.; VILEGAS, WAGNER; DOS SANTOS, LOURDES C.. New Benzaldehyde and Benzopyran Compounds from the Endophytic Fungus Paraphaeosphaeria sp. F03 and Their Antimicrobial and Cytotoxic Activities *. Planta Medica, v. 85, n. 11/12, p. 8-pg., 2019-08-01. (15/11058-5, 14/25222-9, 16/23794-0, 15/04899-3)