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

Mora Vargas, Jorge Andrés [UNESP]; Ortega, Julieth Orduña [UNESP]; dos Santos, Maitê Bernardo Correia [UNESP]; Metzker, Gustavo [UNESP]; Gomes, Eleni [UNESP]; Boscolo, Mauricio [UNESP]

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

Data

2020-03-01

Autores

Mora Vargas, Jorge Andrés

Ortega, Julieth Orduña

dos Santos, Maitê Bernardo Correia

Metzker, Gustavo

Gomes, Eleni

Boscolo, Mauricio

Tipo

Artigo

Resumo

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 32 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 1H and 13C 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.