An Efficient Lipase-Catalyzed Synthesis of Fatty Acid Derivatives of Vanillylamine with Antiherpetic Activity in Acyclovir-Resistant Strains

A series of eleven N-fatty acid derivatives of vanillylamine was synthesized following an enzymatic approach, in excellent yield and a chemoselective way. The excellent results obtained by catalysis of Thermomyces lanuginosus lipase made the procedure very efficient, considering the low amount of en...

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Detalles Bibliográficos
Publicado: 2017
Materias:
Antivirals
Enzymatic synthesis
Molecular modeling
N-vanillylamides
Thermomyces lanuginosus
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_23656549_v2_n4_p1537_Chanquia
http://hdl.handle.net/20.500.12110/paper_23656549_v2_n4_p1537_Chanquia
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_23656549_v2_n4_p1537_Chanquia
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spelling paper:paper_23656549_v2_n4_p1537_Chanquia2023-06-08T16:35:51Z An Efficient Lipase-Catalyzed Synthesis of Fatty Acid Derivatives of Vanillylamine with Antiherpetic Activity in Acyclovir-Resistant Strains Antivirals Enzymatic synthesis Molecular modeling N-vanillylamides Thermomyces lanuginosus A series of eleven N-fatty acid derivatives of vanillylamine was synthesized following an enzymatic approach, in excellent yield and a chemoselective way. The excellent results obtained by catalysis of Thermomyces lanuginosus lipase made the procedure very efficient, considering the low amount of enzyme required and its lower price in comparison with other commercial lipases. The influence of various reaction parameters in the lipase-catalyzed reactions, such as enzyme source, nucleophile/substrate ratio, enzyme/substrate ratio, solvent and temperature, was studied. In order to evaluate the influence of the fatty acid chain length and configuration on the reaction rate and yield, HPLC analysis and molecular modeling experiments were performed. The results showed that a chain length between 12–14 carbon atoms favors the activity of the enzyme, while insaturation had no effect on the reaction rate. These facts confirm the experimental results. In addition, some of the evaluated compounds exhibited antiviral activity against Herpes simplex virus type 1 (HSV-1) KOS strain (TK+) and Field and B2006 strains (TK-) in Vero cells. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2017 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_23656549_v2_n4_p1537_Chanquia http://hdl.handle.net/20.500.12110/paper_23656549_v2_n4_p1537_Chanquia
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Antivirals
Enzymatic synthesis
Molecular modeling
N-vanillylamides
Thermomyces lanuginosus
spellingShingle Antivirals
Enzymatic synthesis
Molecular modeling
N-vanillylamides
Thermomyces lanuginosus
An Efficient Lipase-Catalyzed Synthesis of Fatty Acid Derivatives of Vanillylamine with Antiherpetic Activity in Acyclovir-Resistant Strains
topic_facet Antivirals
Enzymatic synthesis
Molecular modeling
N-vanillylamides
Thermomyces lanuginosus
description A series of eleven N-fatty acid derivatives of vanillylamine was synthesized following an enzymatic approach, in excellent yield and a chemoselective way. The excellent results obtained by catalysis of Thermomyces lanuginosus lipase made the procedure very efficient, considering the low amount of enzyme required and its lower price in comparison with other commercial lipases. The influence of various reaction parameters in the lipase-catalyzed reactions, such as enzyme source, nucleophile/substrate ratio, enzyme/substrate ratio, solvent and temperature, was studied. In order to evaluate the influence of the fatty acid chain length and configuration on the reaction rate and yield, HPLC analysis and molecular modeling experiments were performed. The results showed that a chain length between 12–14 carbon atoms favors the activity of the enzyme, while insaturation had no effect on the reaction rate. These facts confirm the experimental results. In addition, some of the evaluated compounds exhibited antiviral activity against Herpes simplex virus type 1 (HSV-1) KOS strain (TK+) and Field and B2006 strains (TK-) in Vero cells. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
title An Efficient Lipase-Catalyzed Synthesis of Fatty Acid Derivatives of Vanillylamine with Antiherpetic Activity in Acyclovir-Resistant Strains
title_short An Efficient Lipase-Catalyzed Synthesis of Fatty Acid Derivatives of Vanillylamine with Antiherpetic Activity in Acyclovir-Resistant Strains
title_full An Efficient Lipase-Catalyzed Synthesis of Fatty Acid Derivatives of Vanillylamine with Antiherpetic Activity in Acyclovir-Resistant Strains
title_fullStr An Efficient Lipase-Catalyzed Synthesis of Fatty Acid Derivatives of Vanillylamine with Antiherpetic Activity in Acyclovir-Resistant Strains
title_full_unstemmed An Efficient Lipase-Catalyzed Synthesis of Fatty Acid Derivatives of Vanillylamine with Antiherpetic Activity in Acyclovir-Resistant Strains
title_sort efficient lipase-catalyzed synthesis of fatty acid derivatives of vanillylamine with antiherpetic activity in acyclovir-resistant strains
publishDate 2017
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_23656549_v2_n4_p1537_Chanquia
http://hdl.handle.net/20.500.12110/paper_23656549_v2_n4_p1537_Chanquia
_version_ 1768543536752361472

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