A new synthetic methodology for pyridinic sucrose esters and their antibacterial effects against Gram-positive and Gram-negative strains

Author(s)

Mora Vargas, Jorge Andres ^[1] ; Ortega, Julieth Orduna ^{[1, 2]} ; Correia dos Santos, Maite Bernardo ^[1] ; Metzker, Gustavo ^[1] ; Gomes, Eleni ^[1] ; Boscolo, Mauricio ^[1]

Affiliation

^[1] Sao Paulo State Univ UNESP, Inst Biosci Humanities & Exact Sci, Sao Jose Do Rio Preto, SP - Brazil

^[2] Univ Santiago Cali, Fac Ciencias Basicas, Campus Pampalinda, Santiago De Cali - Colombia

• Document type: Journal article
• Source: Carbohydrate Research; v. 489, MAR 2020.
• Web of Science Citations: 0

Abstract

Described are the development of a new synthetic method using ultrasonic irradiation and sodium methoxide as catalyst for a series of pyridinic sucrose esters (py-SEs), derived from transesterification of sucrose with picolinic, nicotinic and isonicotinic methyl esters. The reaction was optimized using a 3(2) x 2 experimental design, the reaction time, temperature and sucrose: methyl ester molar ratio being evaluated. The method proved to be efficient for obtaining monosubstituted esters (>= 83%) with high methyl ester consumption (>= 79%). The monosubstituted py-SEs were isolated by semipreparative HPLC, characterized by high-resolution mass spectrometry, calorimetry, vibrational spectroscopy, and H-1 and C-13 NMR. The py-SEs were tested against E. coli, S. aureos, and P. aeruginosa bacteria with minimum inhibitory concentration values equal or inferior to the reference drugs for both E. coli and P. aeruginosa. (AU)

• FAPESP's process: 17/09520-8 - Sucrose pyridinic esters: synthesis, characterization and antimicrobial activity: evaluation of the synthesis parameters by acoustic cavitation
• Grantee: Jorge Andrés Mora Vargas
• Support Opportunities: Scholarships in Brazil - Master
• FAPESP's process: 17/13230-5 - Partial ethanol reforming: stability and selectivity of mix metal amphoteric oxides as catalysts for atmospheric pressure flow reaction
• Grantee: Mauricio Boscolo
• Support Opportunities: Program for Research on Bioenergy (BIOEN) - Regular Program Grants