Syntheses of dipeptide alcohols and dipeptide aldehyde precursors catalyzed by plant cysteine peptidases

Autores
Morcelle del Valle, Susana Raquel; Cánepa, Alicia Susana; Padró, Juan Manuel; Llerena Suster, Carlos Rafael; Clepés, Pere
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Two different cysteine peptidases obtained from plant latex (papain from Carica papaya and araujiain from Araujia hortorum) demonstrated to be good catalysts for the condensation of coded and non-coded Cbz-amino acids and amines such as amino alcohols and amino acetals in acetonitrile containing 1% (v/v) water. Both kinetically and thermodynamically controlled syntheses were proved. Thermodynamic approach was selected since the conversions in product found were similar to those obtained by the kinetic approach; furthermore, a minor number of synthetic steps were needed. For the Cbz-amino acids tested, conversions were higher than 80% at 48-72 h of reaction, except for the Phg derivative, which produced conversions of ca. 40 and 20% for papain and araujiain, respectively. Product yields for the scaled up reactions were similar to the conversions obtained in microscale synthesis. The flexibility of both enzymes for the nucleophile allowed the condensation reaction of Cbz-Ala-OH with an amino diacetal derivative. The resulting dipeptide diacetal derivative can be easily tranformed into a dipeptide aldehyde by acid hydrolysis.
Fil: Morcelle del Valle, Susana Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Ciencias Biológicas. Laboratorio de Investigación de Proteínas Vegetales; Argentina
Fil: Cánepa, Alicia Susana. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Padró, Juan Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Grupo Cromatografía; Argentina
Fil: Llerena Suster, Carlos Rafael. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Ciencias Biológicas. Laboratorio de Investigación de Proteínas Vegetales; Argentina
Fil: Clepés, Pere. Consejo Superior de Investigaciones Científicas. Instituto de Química Avanzada de Catalunya; España
Materia
Coded And No-Coded Amino Acids
Dipeptide Alcohol
Dipeptide Aldehyde
Plant Peptidases
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/76754
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Syntheses of dipeptide alcohols and dipeptide aldehyde precursors catalyzed by plant cysteine peptidasesMorcelle del Valle, Susana RaquelCánepa, Alicia SusanaPadró, Juan ManuelLlerena Suster, Carlos RafaelClepés, PereCoded And No-Coded Amino AcidsDipeptide AlcoholDipeptide AldehydePlant Peptidaseshttps://purl.org/becyt/ford/2.9https://purl.org/becyt/ford/2Two different cysteine peptidases obtained from plant latex (papain from Carica papaya and araujiain from Araujia hortorum) demonstrated to be good catalysts for the condensation of coded and non-coded Cbz-amino acids and amines such as amino alcohols and amino acetals in acetonitrile containing 1% (v/v) water. Both kinetically and thermodynamically controlled syntheses were proved. Thermodynamic approach was selected since the conversions in product found were similar to those obtained by the kinetic approach; furthermore, a minor number of synthetic steps were needed. For the Cbz-amino acids tested, conversions were higher than 80% at 48-72 h of reaction, except for the Phg derivative, which produced conversions of ca. 40 and 20% for papain and araujiain, respectively. Product yields for the scaled up reactions were similar to the conversions obtained in microscale synthesis. The flexibility of both enzymes for the nucleophile allowed the condensation reaction of Cbz-Ala-OH with an amino diacetal derivative. The resulting dipeptide diacetal derivative can be easily tranformed into a dipeptide aldehyde by acid hydrolysis.Fil: Morcelle del Valle, Susana Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Ciencias Biológicas. Laboratorio de Investigación de Proteínas Vegetales; ArgentinaFil: Cánepa, Alicia Susana. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; ArgentinaFil: Padró, Juan Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Grupo Cromatografía; ArgentinaFil: Llerena Suster, Carlos Rafael. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Ciencias Biológicas. Laboratorio de Investigación de Proteínas Vegetales; ArgentinaFil: Clepés, Pere. Consejo Superior de Investigaciones Científicas. Instituto de Química Avanzada de Catalunya; EspañaElsevier Science2013-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/76754Morcelle del Valle, Susana Raquel; Cánepa, Alicia Susana; Padró, Juan Manuel; Llerena Suster, Carlos Rafael; Clepés, Pere; Syntheses of dipeptide alcohols and dipeptide aldehyde precursors catalyzed by plant cysteine peptidases; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 89; 5-2013; 130-1361381-1177CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1381117712003220info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2012.12.004info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:42:43Zoai:ri.conicet.gov.ar:11336/76754instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-15 15:42:43.758CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Syntheses of dipeptide alcohols and dipeptide aldehyde precursors catalyzed by plant cysteine peptidases
title Syntheses of dipeptide alcohols and dipeptide aldehyde precursors catalyzed by plant cysteine peptidases
spellingShingle Syntheses of dipeptide alcohols and dipeptide aldehyde precursors catalyzed by plant cysteine peptidases
Morcelle del Valle, Susana Raquel
Coded And No-Coded Amino Acids
Dipeptide Alcohol
Dipeptide Aldehyde
Plant Peptidases
title_short Syntheses of dipeptide alcohols and dipeptide aldehyde precursors catalyzed by plant cysteine peptidases
title_full Syntheses of dipeptide alcohols and dipeptide aldehyde precursors catalyzed by plant cysteine peptidases
title_fullStr Syntheses of dipeptide alcohols and dipeptide aldehyde precursors catalyzed by plant cysteine peptidases
title_full_unstemmed Syntheses of dipeptide alcohols and dipeptide aldehyde precursors catalyzed by plant cysteine peptidases
title_sort Syntheses of dipeptide alcohols and dipeptide aldehyde precursors catalyzed by plant cysteine peptidases
dc.creator.none.fl_str_mv Morcelle del Valle, Susana Raquel
Cánepa, Alicia Susana
Padró, Juan Manuel
Llerena Suster, Carlos Rafael
Clepés, Pere
author Morcelle del Valle, Susana Raquel
author_facet Morcelle del Valle, Susana Raquel
Cánepa, Alicia Susana
Padró, Juan Manuel
Llerena Suster, Carlos Rafael
Clepés, Pere
author_role author
author2 Cánepa, Alicia Susana
Padró, Juan Manuel
Llerena Suster, Carlos Rafael
Clepés, Pere
author2_role author
author
author
author
dc.subject.none.fl_str_mv Coded And No-Coded Amino Acids
Dipeptide Alcohol
Dipeptide Aldehyde
Plant Peptidases
topic Coded And No-Coded Amino Acids
Dipeptide Alcohol
Dipeptide Aldehyde
Plant Peptidases
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.9
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv Two different cysteine peptidases obtained from plant latex (papain from Carica papaya and araujiain from Araujia hortorum) demonstrated to be good catalysts for the condensation of coded and non-coded Cbz-amino acids and amines such as amino alcohols and amino acetals in acetonitrile containing 1% (v/v) water. Both kinetically and thermodynamically controlled syntheses were proved. Thermodynamic approach was selected since the conversions in product found were similar to those obtained by the kinetic approach; furthermore, a minor number of synthetic steps were needed. For the Cbz-amino acids tested, conversions were higher than 80% at 48-72 h of reaction, except for the Phg derivative, which produced conversions of ca. 40 and 20% for papain and araujiain, respectively. Product yields for the scaled up reactions were similar to the conversions obtained in microscale synthesis. The flexibility of both enzymes for the nucleophile allowed the condensation reaction of Cbz-Ala-OH with an amino diacetal derivative. The resulting dipeptide diacetal derivative can be easily tranformed into a dipeptide aldehyde by acid hydrolysis.
Fil: Morcelle del Valle, Susana Raquel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Ciencias Biológicas. Laboratorio de Investigación de Proteínas Vegetales; Argentina
Fil: Cánepa, Alicia Susana. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina
Fil: Padró, Juan Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Grupo Cromatografía; Argentina
Fil: Llerena Suster, Carlos Rafael. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata; Argentina. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Ciencias Biológicas. Laboratorio de Investigación de Proteínas Vegetales; Argentina
Fil: Clepés, Pere. Consejo Superior de Investigaciones Científicas. Instituto de Química Avanzada de Catalunya; España
description Two different cysteine peptidases obtained from plant latex (papain from Carica papaya and araujiain from Araujia hortorum) demonstrated to be good catalysts for the condensation of coded and non-coded Cbz-amino acids and amines such as amino alcohols and amino acetals in acetonitrile containing 1% (v/v) water. Both kinetically and thermodynamically controlled syntheses were proved. Thermodynamic approach was selected since the conversions in product found were similar to those obtained by the kinetic approach; furthermore, a minor number of synthetic steps were needed. For the Cbz-amino acids tested, conversions were higher than 80% at 48-72 h of reaction, except for the Phg derivative, which produced conversions of ca. 40 and 20% for papain and araujiain, respectively. Product yields for the scaled up reactions were similar to the conversions obtained in microscale synthesis. The flexibility of both enzymes for the nucleophile allowed the condensation reaction of Cbz-Ala-OH with an amino diacetal derivative. The resulting dipeptide diacetal derivative can be easily tranformed into a dipeptide aldehyde by acid hydrolysis.
publishDate 2013
dc.date.none.fl_str_mv 2013-05
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/76754
Morcelle del Valle, Susana Raquel; Cánepa, Alicia Susana; Padró, Juan Manuel; Llerena Suster, Carlos Rafael; Clepés, Pere; Syntheses of dipeptide alcohols and dipeptide aldehyde precursors catalyzed by plant cysteine peptidases; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 89; 5-2013; 130-136
1381-1177
CONICET Digital
CONICET
url http://hdl.handle.net/11336/76754
identifier_str_mv Morcelle del Valle, Susana Raquel; Cánepa, Alicia Susana; Padró, Juan Manuel; Llerena Suster, Carlos Rafael; Clepés, Pere; Syntheses of dipeptide alcohols and dipeptide aldehyde precursors catalyzed by plant cysteine peptidases; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 89; 5-2013; 130-136
1381-1177
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1381117712003220
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2012.12.004
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.22299

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