Chemoenzymatic Synthesis of the New 3-((2,3-Diacetoxypropanoyl)oxy)propane-1,2-diyl Diacetate Using Immobilized Lipase B from Candida antarctica and Pyridinium Chlorochromate as an Oxidizing Agent

International Journal of Molecular Sciences

Claudia Ortiz¹  JohnJ. Castillo²  Jennifer Ruiz²  Mónica Ruiz²  Esteban Plata²  Roberto Fernández-Lafuente³ 

[1] Escuela de Microbiología, Universidad Industrial de Santander, 680001 Bucaramanga, Colombia;Escuela de Química, Grupo de investigación en Bioquímica y Microbiología (GIBIM), Edificio Camilo Torres 210, Universidad Industrial de Santander, CEP, 680001 Bucaramanga, Colombia;ICP-CSIC, Campus UAM-CSIC, Cantoblanco, 28049 Madrid, Spain;

关键词: chemoenzymatic synthesis;    glycerol derivatives;    interfacially activated lipase;    regioselective hydrolysis;    diacetin oxidation;    pyridinium chlorochromate;   

DOI  :  10.3390/ijms21186501

来源: DOAJ

【 摘 要 】

To exploit the hydrolytic activity and high selectivity of immobilized lipase B from Candida antarctica on octyl agarose (CALB-OC) in the hydrolysis of triacetin and also to produce new value-added compounds from glycerol, this work describes a chemoenzymatic methodology for the synthesis of the new dimeric glycerol ester 3-((2,3-diacetoxypropanoyl)oxy)propane-1,2-diyl diacetate. According to this approach, triacetin was regioselectively hydrolyzed to 1,2-diacetin with CALB-OC. The diglyceride product was subsequently oxidized with pyridinium chlorochromate (PCC) and a dimeric ester was isolated as the only product. It was found that the medium acidity during the PCC treatment and a high 1,2-diacetin concentration favored the formation of the ester. The synthesized compounds were characterized using IR, MS, HR-MS, and NMR techniques. The obtained dimeric ester was evaluated at 100 ppm against seven bacterial strains and two Candida species to identify its antimicrobial activity. The compound has no inhibitory activity against the bacterial strains used but decreased C. albicans and C. parapsilosis growth by 49% and 68%, respectively. Hemolytic activity was evaluated, and the results obtained support the use of the dimeric ester to control C. albicans and C. parapsilosis growth in non-intravenous applications because the compound shows hemolytic activity.

【 授权许可】

Unknown