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Abstract:

A series of cholic acid derivatives was synthesized by enzyme catalysis. Eleven acetyl and ester derivatives of cholic acid, eight of them new compounds, were obtained through regioselective lipase-catalyzed reactions in very good to excellent yield. The influence of various reaction parameters in the enzymatic esterification, acetylation and alcoholysis reactions, such as enzyme source, alcohol or acylating agent: substrate ratio, enzyme: substrate ratio, solvent and temperature, was studied. Moreover, in order to shed light to cholic acid behavior in the enzymatic reactions, molecular docking of the lipase with cholic acid and some derivatives was carried out. © 2015 Elsevier Inc. All rights reserved.

Registro:

Documento: Artículo
Título:New cholic acid derivatives: Biocatalytic synthesis and molecular docking study
Autor:Zígolo, M.A.; García Liñares, G.; Baldessari, A.
Filiación:Laboratorio de Biocatálisis, Departamento de Química Orgánica y UMYMFOR, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, piso 3, Buenos Aires, C1428EGA, Argentina
Palabras clave:Cholic acid; Lipase-catalyzed; Molecular docking; 3alpha,7alpha,12alpha triacetoxy 5beta cholanic acid; alcohol; butanol; butyl 3alpha,7alpha,12alpha trihydroxy 5beta cholanate; cholic acid; cholic acid derivative; dodecyl 3alpha,7alpha,12alpha trihydroxy 5beta cholanate; ethyl 3alpha acetoxy 7alpha,12alpha dihydroxy 5beta cholanate; ethyl 3alpha,7alpha,12alpha triacetoxy 5beta cholanate; ethyl 3alpha,7alpha,12alpha trihydroxy 5beta cholanate; ethyl 7alpha,12alpha diacetoxy 3alpha dihydroxy 5beta cholanate; hexadecanol; hexadecyl 3alpha,7alpha,12alpha trihydroxy 5beta cholanate; lauryl alcohol; myristyl alcohol; octadecanol; octadecyl 3alpha,7alpha,12alpha trihydroxy 5beta cholanate; propanol; solvent; tetradecyl 3alpha,7alpha,12alpha trihydroxy 5beta cholanate; triacylglycerol lipase; unclassified drug; cholic acid derivative; Lipozyme; acetylation; alcoholysis; Article; biocatalysis; esterification; molecular docking; synthesis; temperature; Cholic Acids; Lipase
Año:2016
Volumen:107
Página de inicio:10
Página de fin:19
DOI: http://dx.doi.org/10.1016/j.steroids.2015.12.014
Título revista:Steroids
Título revista abreviado:Steroids
ISSN:0039128X
CODEN:STEDA
CAS:alcohol, 64-17-5; butanol, 35296-72-1, 71-36-3; cholic acid, 32500-01-9, 361-09-1, 81-25-4; hexadecanol, 29354-98-1, 36653-82-4, 51260-59-4; lauryl alcohol, 112-53-8, 27342-88-7; myristyl alcohol, 112-72-1, 27196-00-5; octadecanol, 112-92-5, 68894-51-9; propanol, 62309-51-7, 71-23-8; triacylglycerol lipase, 9001-62-1; Cholic Acids; Lipase; Lipozyme
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v107_n_p10_Zigolo

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Citas:

---------- APA ----------
Zígolo, M.A., García Liñares, G. & Baldessari, A. (2016) . New cholic acid derivatives: Biocatalytic synthesis and molecular docking study. Steroids, 107, 10-19.
http://dx.doi.org/10.1016/j.steroids.2015.12.014
---------- CHICAGO ----------
Zígolo, M.A., García Liñares, G., Baldessari, A. "New cholic acid derivatives: Biocatalytic synthesis and molecular docking study" . Steroids 107 (2016) : 10-19.
http://dx.doi.org/10.1016/j.steroids.2015.12.014
---------- MLA ----------
Zígolo, M.A., García Liñares, G., Baldessari, A. "New cholic acid derivatives: Biocatalytic synthesis and molecular docking study" . Steroids, vol. 107, 2016, pp. 10-19.
http://dx.doi.org/10.1016/j.steroids.2015.12.014
---------- VANCOUVER ----------
Zígolo, M.A., García Liñares, G., Baldessari, A. New cholic acid derivatives: Biocatalytic synthesis and molecular docking study. Steroids. 2016;107:10-19.
http://dx.doi.org/10.1016/j.steroids.2015.12.014