Enabling technologies for the sustainable chemical synthesis of platform molecules, new chemicals and bioactive compounds

• Grant number: 21/06661-5
• Support Opportunities: Program for Research on Bioenergy (BIOEN) - Young Investigators Grants - Phase 2
• Start date: April 01, 2022
• End date: March 31, 2027
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Júlio Cezar Pastre
• Grantee: Júlio Cezar Pastre
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Associated researchers: Duncan Leonard Browne ; Gianvito Vilé ; Ricardo Labes ; Richard Anthony Bourne
• Associated research grant: 14/26378-2 - Development of methodologies and synthetic processes employing a new technological platform: micro and meso reactor assisted synthesis of natural products and derivatives with potential pharmacological activity, AP.JP
• Associated scholarship(s): 24/18522-8 - Valorization of Lignin for the Synthesis of Cyclohexenones Using Electrochemical Reductive Processes, BP.IC; 24/15116-9 - Valorization of Chitin Biomass for the Synthesis of Nitrogenated Aromatic Compounds., BP.IC; 24/12646-7 - Synthesis of New Plasticizers Obtained from Renewable Sources., BP.IC; + associated scholarships 24/00753-3 - General and Operational Technical Training in Organic Chemistry Laboratory., BP.TT; 23/15576-7 - Integrated Synthesis of Butenolides in Continuous Flow Regime., BP.IC; 23/07466-7 - Development of Self-Optimization Platforms for the Multi-Step Synthesis of APIs, BP.PD; 23/08725-6 - Synthesis of New Building Blocks Derived from Terpenes., BP.MS; 23/01930-3 - Conversion of biomass derivatives to high value materials and green solvents for high valuable chemicals, BP.PD; 23/05347-0 - General and Operational Technical Training in Organic Chemistry Laboratory., BP.TT; 22/15574-1 - Enantioselective Photocatalysis in Continuous Flow Applied to the Synthesis of Bioactive Compounds and APIs, BP.PD; 23/01238-2 - Synthesis of new aromatic compounds derived from renewable sources, BP.DD; 23/01232-4 - Exploring the benefits of enabling technologies in the synthesis of platform molecules, BP.DD; 22/00774-5 - Employment of renewable chemical platforms to obtain synthetic intermediates with higher added-value., BP.PD - associated scholarships

Abstract

Raw materials from renewable sources, as well as agro-industrial waste, represent an attractive source of useful chemical functionalities, which to date is still largely untapped in terms of their application in the fine chemicals industry. Our research group has already identified continuous flow processing as a fundamental technology for the valorization of such materials, so that any designed methods can be rapidly scaled to manufacture. Many of the principles of Green Chemistry and Sustainability can be met by embracing new technologies that are inherently cleaner when compared to the current status quo. By designing new synthetic methods that take full advantage of the capabilities of different enabling technologies, one will inevitably end up with greener, cleaner processes.In this proposal, reactions will be explored in continuous flow regime, under microwave irradiation or under mechanochemical conditions in the processing of compounds derived from an extremely rich and abundant feedstock in Brazil: the biomass. The project comprises 3 strategic research axes, whose main objective is to explore the benefits of these three enabling technologies in the chemical conversion of biomass-derived compounds to obtaining platform molecules (Axis 1) and new chemicals or building blocks (Axis 2), as well as in the synthesis of bioactive compounds such as APIs and other relevant bioactive compounds (Axis 3).Analytical tools, such as design of experiments (DoE) will be employed in order to quickly map reaction conditions and assess the effect of various parameters, minimizing the time needed to optimizing processes. Likewise, continuous flow systems combined with in-line analytical tools and optimization algorithms will also be adopted in the development of new automated synthetic processes (so-called 'self-optimization'). The ability of self-optimization to efficiently identify optimal operating conditions in a multivariate parameter space has presented many opportunities for more efficient process development. Such advantages align with the rising interest in continuous flow chemistry towards the 'greener' synthesis of active pharmaceutical ingredients (APIs), and offer the potential to reduce the drug development timeline. Thus, the adoption of these tools is very timely. (AU)

Scientific publications

(9)

(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)

ANHOLETO, LUIS ADRIANO; BRANCAGLION, GUILHERME ANDRADE; DOS SANTOS, DANILO MARTINS; KAPRITCHKOFF, RAFAELA TAMI IKEDA; CASTRO, KARINA NEOOB DE CARVALHO; CANUTO, KIRLEY MARQUES; RODRIGUES, RODNEY ALEXANDRE FERREIRA; CORREA, DANIEL SOUZA; CHAGAS, ANA CAROLINA DE SOUZA; PASTRE, JULIO CEZAR. Acaricidal activity of synthetic spilanthol derivative against ticks of medical and veterinary importance. Veterinary Parasitology, v. 327, p. 9-pg., 2024-01-25. (22/00776-8, 21/10004-0, 21/06661-5, 18/22214-6, 19/20185-1)

LOPES, ERIC F.; COSTA E SILVA, RODRIGO; SOUZA, RAFAEL A. C.; FERNANDEZ, PABLO SEBASTIAN; PASTRE, JULIO CEZAR. Stereoselective Electrochemical Synthesis of E-Tetrasubstituted Haloalkenyl Chalcogenides. CHEMISTRY-AN ASIAN JOURNAL, v. N/A, p. 8-pg., 2024-10-31. (23/07466-7, 23/02929-9, 23/01930-3, 21/06661-5, 17/11986-5)

MATTIOLI, RENAN RODINI; SANTOS, CAMILA SOUZA; DE SOUZA, BRUNA BUTKE; BRANCO, PEDRO DOMINGUEZ; BOLT, ROBERT R. A.; RABY-BUCK, SARAH E.; CABRAL, TADEU LUIZ GOMES; TORMENA, CLAUDIO F.; BROWNE, DUNCAN L.; PASTRE, JULIO C.. On the Valorisation of Chitin-Derived Furans by Milling. CHEMSUSCHEM, v. N/A, p. 6-pg., 2024-10-30. (21/05081-5, 22/00774-5, 19/26450-9, 22/03872-8, 20/10246-0, 21/06661-5, 23/01238-2, 23/01232-4)

FERREIRA, LUCAS CORAL; GALAVERNA, RENAN DE SOUZA; MCBRIDE, TOM; SILVA, RODRIGO COSTA E; BROWNE, DUNCAN L.; PASTRE, JULIO CEZAR. Fast and scalable continuous flow synthesis of butenolides and coumarins. REACTION CHEMISTRY & ENGINEERING, v. N/A, p. 6-pg., 2025-02-10. (21/06661-5, 23/07466-7)

COSTA, RENNA K. E.; BRANCAGLION, GUILHERME A.; PINHEIRO, MATHEUS P.; ADAMOSKI, DOUGLAS; DA SILVA, BIANCA N.; NEGRAO, CYRO Z. DE V.; GONCALVES, KALIANDRA DE A.; RODRIGUES, CAMILA T.; AMBROSIO, ANDRE L. B.; GUIDO, RAFAEL V. C.; et al. Discovery of aminothiazole derivatives as a chemical scaffold for glutaminase inhibition. RESULTS IN CHEMISTRY, v. 5, p. 17-pg., 2023-02-17. (13/07600-3, 16/09077-4, 21/13736-1, 14/26378-2, 19/16351-3, 20/12904-5, 21/06661-5, 14/15968-3)

GOMES, GUSTAVO R.; SCOPEL, EUPIDIO; ROCHA, NICOLA L.; BREITKREITZ, MARCIA C.; CORMANICH, RODRIGO A.; REZENDE, CAMILA A.; PASTRE, JULIO C.. Direct Ethyl Levulinate Production from Raw Lignocellulosic Biomass Mediated by a Novel Taurine-Based Imidazolium Ionic Liquid. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, v. N/A, p. 13-pg., 2022-11-21. (18/23769-1, 18/09861-2, 14/26378-2, 18/03910-1, 21/06661-5, 19/19360-3, 14/25770-6, 20/11578-7)

SMALLMAN, HARRY R.; BRANCAGLION, GUILHERME A.; PASTRE, JULIO C.; BROWNE, DUNCAN L.. Continuous Flow Generation of Acylketene Intermediates via Nitrogen Extrusion. Journal of Organic Chemistry, v. 87, n. 18, p. 9-pg., 2022-09-01. (21/06661-5)

GOMES, GUSTAVO R.; SCOPEL, EUPIDIO; BREITKREITZ, MARCIA C.; REZENDE, CAMILA A.; PASTRE, JULIO C.. Valorization of sugarcane bagasse C5-fraction by furfural production mediated by renewable glycine-based ionic liquid. INDUSTRIAL CROPS AND PRODUCTS, v. 191, p. 11-pg., 2023-01-01. (18/09861-2, 18/23769-1, 14/26378-2, 21/06661-5, 20/11578-7, 19/19360-3, 14/25770-6)

SANTOS, CAMILA SOUZA; MATTIOLI, RENAN RODINI; BAPTISTA, JULIA SOARES; DA SILVA, VITOR MENEZES H.; BROWNE, DUNCAN L.; PASTRE, JULIO CEZAR. Nitrogenated aromatics from chitin. GREEN CHEMISTRY, v. 25, n. 13, p. 10-pg., 2023-04-14. (19/26450-9, 22/03872-8, 21/06661-5, 22/00774-5)