Sucrose pyridinic esters: synthesis, characterization and antimicrobial activity: evaluation of the synthesis parameters by acoustic cavitation

• Grant number: 17/09520-8
• Support Opportunities: Scholarships in Brazil - Master
• Start date: January 01, 2018
• End date: May 31, 2019
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Mauricio Boscolo
• Grantee: Jorge Andrés Mora Vargas
• Host Institution: Instituto de Biociências, Letras e Ciências Exatas (IBILCE). Universidade Estadual Paulista (UNESP). Campus de São José do Rio Preto. São José do Rio Preto , SP, Brazil

Abstract

The interest in sucrose derivatives has been increased due their different applications in various industrial sectors (pharmaceutical, cosmetic, bioengineering, chemistry, agriculture and food). One of the characteristics of sucrose is its behavior as a polyol, which allows synthesizing many value-added compounds, as well as being a low cost and environmentally friendly reagent. Sucrose esters are one of the possibilities of sugar derivatives with characteristics of non-ionic surfactants, emulsifiers, microbiological controllers, among others, and according to the nature of the acid group introduced into the sucrose molecule, may have different applications. On the other hand, pyridinic acids have been studied as antimicrobial agents, anticancer agents, dietary supplements, and thus are still unexplored. This study aims to synthesize pyridinic sucrose esters by transesterification reactions with homogeneous catalysis (sodium methoxide) with four pyridinic acids methyl esters (picolinic, nicotinic, isonicotinic and orotic) under ultrasound irradiation (20 kHz). Because of the polyactivity of sucrose, to control which and how many hydroxyls will undergo substitution is very difficult. In order to understand the factors governing the formation of the preferred regio-isomers derived from each pyridinic acid under different synthesis conditions, a factorial xn will be executed with the following three factors: (i) temperature (30 and 70 oC), (ii) The molar ratio of the starting ester to the sucrose (1: 1, 1: 2 and 1: 3); (Iii) reaction time (10, 20 and 30 min). In the conditions with the best synthesis yields, the influence of polyvalent metal ions (Cu2 +, Mn2 +, Fe3 +, Nb5 +) on the formation of regioisomers will also be tested. In this process the heterogeneous catalysis potential will also be studied by employing the solid Mg6Al2Ox as the catalyst. The products will be separated by preparative chromatography and the characterization will be done by refractive index, LC-ES-MS, ATR-FTIR, CHN and NMR, to observe the different degrees of esterification as well as the regioisomers, which should be tested for antimicrobial activity (two Gram + and two Gram -) by disc diffusion assay. (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)

METZKER, GUSTAVO; VARGAS, JORGE ANDRES MORA; DE LIMA, LIVIA PADILHA; PERRONE, OLAVO MICALI; SIQUEIRA, MARCOS RECHI; VARANDA, LAUDEMIR CARLOS; BOSCOLO, MAURICIO. First row transition metals on the ethanol Guerbet reaction: Products distribution and structural behavior of mixed metal oxides as catalysts. APPLIED CATALYSIS A-GENERAL, v. 623, AUG 5 2021. (92/03515-3, 20/02471-4, 19/11058-6, 17/09520-8)

NASCIMENTO, PATRICIA A.; SCHULTZ, JULIANA; GONZALEZ, MARIO H.; OLIVEIRA, ANDREA. Simple GFAAS Method for Determination of Pb, As, and Cd in Cannabidiol Extracts Used for Therapeutic Purposes. Journal of the Brazilian Chemical Society, v. 31, n. 5, p. 894-903, MAY 2020. (13/23886-4, 17/09520-8, 17/13230-5, 17/18531-3, 15/08873-9)

SANTANA, ANA PR; MORA-VARGAS, JORGE A.; GUIMARAES, TACIANA G. S.; AMARAL, CLARICE D. B.; OLIVEIRA, ANDREA; GONZALEZ, MARIO H.. Sustainable synthesis of natural deep eutectic solvents (NADES) by different methods. JOURNAL OF MOLECULAR LIQUIDS, v. 293, NOV 1 2019. (17/09520-8, 17/13230-5, 13/23886-4, 15/08873-9, 17/18531-3)

METZKER, GUSTAVO; MORA VARGAS, JORGE ANDRES; BOSCOLO, MAURICIO; FORD, PC; VANELDIK, R. Heterogeneous catalytic ethanol transformation into chemicals: Some Brazilian contributions. CATALYSIS IN BIOMASS CONVERSION, v. 77, p. 33-pg., 2021-01-01. (17/09520-8, 17/13230-5)

MORA VARGAS, JORGE ANDRES; ORDUNA ORTEGA, JULIETH; METZKER, GUSTAVO; ELIECER LARRAHONDO, JESUS; BOSCOLO, MAURICIO. Natural sucrose esters: Perspectives on the chemical and physiological use of an under investigated chemical class of compounds. Phytochemistry, v. 177, SEP 2020. (17/09520-8, 17/13230-5)

MORA VARGAS, JORGE ANDRES; ORTEGA, JULIETH ORDUNA; CORREIA DOS SANTOS, MAITE BERNARDO; METZKER, GUSTAVO; GOMES, ELENI; BOSCOLO, MAURICIO. A new synthetic methodology for pyridinic sucrose esters and their antibacterial effects against Gram-positive and Gram-negative strains. Carbohydrate Research, v. 489, MAR 2020. (17/09520-8, 17/13230-5)

ORTEGA, JULIETH ORDUNA; MORA VARGAS, JORGE ANDRES; PERRONE, OLAVO MICALI; METZKER, GUSTAVO; GOMES, ELENI; DA SILVA, ROBERTO; BOSCOLO, MAURICIO. Soaking and ozonolysis pretreatment of sugarcane straw for the production of fermentable sugars. INDUSTRIAL CROPS AND PRODUCTS, v. 145, MAR 2020. (10/12624-0, 17/13230-5, 17/09520-8, 15/11588-4)

ORDUNA ORTEGA, JULIETH; MORA VARGAS, JORGE ANDRES; METZKER, GUSTAVO; GOMES, ELENI; DA SILVA, ROBERTO; BOSCOLO, MAURICIO. Enhancing the production of the fermentable sugars from sugarcane straw: A new approach to applying alkaline and ozonolysis pretreatments. RENEWABLE ENERGY, v. 164, p. 502-508, FEB 2021. (14/02080-4, 17/13230-5, 15/11588-4, 17/09520-8, 10/12624-0)

MORA VARGAS, JORGE; TOFANELI MORELATO, LUIZ HENRIQUE; ORDUNA ORTEGA, JULIETH; BOSCOLO, MAURICIO; METZKER, GUSTAVO. Upgrading 1-butanol to unsaturated, carbonyl and aromatic compounds: a new synthesis approach to produce important organic building blocks. GREEN CHEMISTRY, v. 22, n. 8, p. 2365-2369, APR 21 2020. (17/09520-8, 17/13230-5)

Academic Publications

(References retrieved automatically from State of São Paulo Research Institutions)

VARGAS, Jorge Andrés Mora. Ésteres piridínicos de sacarose: síntese, caracterização e atividade antimicrobiana. Avaliação de parâmetros de síntese por cavitação acústica.. 2019. Master's Dissertation - Universidade Estadual Paulista (Unesp). Instituto de Biociências Letras e Ciências Exatas. São José do Rio Preto São José do Rio Preto.