Enzyme-catalyzed preparation of chenodeoxycholic esters by an immobilized heterologous Rhizopus oryzae lipase
Quintana, Paula G. (Universidad de Buenos Aires. Departamento de Química Orgánica)
Canet, Albert (Universitat Autònoma de Barcelona. Departament d'Enginyeria Química)
Marciello, Marzia (Universidad Autónoma de Madrid. Departamento de Biocatálisis)
Valero Barranco, Francisco (Universitat Autònoma de Barcelona. Departament d'Enginyeria Química)
Palomo, Jose M. (Universidad Autónoma de Madrid. Departamento de Biocatálisis)
Baldessari, Alicia (Universidad de Buenos Aires. Departamento de Química Orgánica)

Data:	2015
Resum:	A lipase-catalyzed preparation of ethyl and stearyl esters of chenodeoxycholic acid is described. Stearyl chenodeoxycholate is a new product and both bile acid esters were prepared through an enzymatic approach for the first time. The heterologous Rhizopus oryzae lipase, immobilized on two different supports proved to be an efficient catalyst, even more active than Candida antarctica lipase, in the esterification reaction using a complex substrate such as a bile acid. The immobilization of the enzyme on Octadecyl Sepabeads at pH 7 and 25 °C was the best choice to catalyze the esterification reaction. The influence of various reaction parameters, such as nature of the alcohol, alcohol:substrate ratio, enzyme:substrate ratio, solvent and temperature, was evaluated. Using the response surface methodology and a central composite rotatable design, the conversion of stearyl chenodeoxycholate was optimized by means of the study of the effect of enzyme:substrate ratio and alcohol:substrate ratio. The value 20 for ratios (E/S) and (A/S) was predicted as the optimal value to reach the maximum conversion. However, including economic aspects these ratios can be reduced up to 15. The well-known advantages of biocatalysis and the activity shown by the immobilized heterologous lipase make the reported procedure a convenient way to prepare chenodeoxycholic esters.
Ajuts:	Ministerio de Economía y Competitividad CTQ2013-42391-R Agència de Gestió d'Ajuts Universitaris i de Recerca 2014/SGR-452
Drets:	Aquest document està subjecte a una llicència d'ús Creative Commons. Es permet la reproducció total o parcial, la distribució, i la comunicació pública de l'obra, sempre que no sigui amb finalitats comercials, i sempre que es reconegui l'autoria de l'obra original. No es permet la creació d'obres derivades.
Llengua:	Anglès
Document:	Article ; recerca ; Versió acceptada per publicar
Matèria:	Chenodeoxycholic acid ; Esterification ; Heterologous Rhizopus oryzae Lipase ; Immobilization
Publicat a:	Journal of Molecular Catalysis B: Enzymatic, Vol. 118 (August 2015) , p. 36-42, ISSN 1873-3158

DOI: 10.1016/j.molcatb.2015.05.008

Postprint 42 p, 1.5 MB

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