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

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%...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autores principales: Morcelle del Valle, Susana Raquel, Cánepa, Alicia Susana, Padró, Juan Manuel, Llerena Suster, Carlos R., Clapés, Pere
Formato: Articulo
Lenguaje:Español
Publicado: 2013
Materias:
Biología
Química
Plant peptidases
Coded and no-coded amino acids
Dipeptide alcohol
Dipeptide aldehyde
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/153064
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-153064
record_format dspace
spelling I19-R120-10915-1530642023-05-17T04:06:09Z http://sedici.unlp.edu.ar/handle/10915/153064 Syntheses of dipeptide alcohols and dipeptide aldehyde precursors catalyzed by plant cysteine peptidases Morcelle del Valle, Susana Raquel Cánepa, Alicia Susana Padró, Juan Manuel Llerena Suster, Carlos R. Clapés, Pere 2013 2023-05-16T14:25:23Z es Biología Química Plant peptidases Coded and no-coded amino acids Dipeptide alcohol Dipeptide aldehyde 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. Centro de Investigación de Proteínas Vegetales Articulo Articulo http://creativecommons.org/licenses/by-nc-sa/4.0/ Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0) application/pdf
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Español
topic Biología
Química
Plant peptidases
Coded and no-coded amino acids
Dipeptide alcohol
Dipeptide aldehyde
spellingShingle Biología
Química
Plant peptidases
Coded and no-coded amino acids
Dipeptide alcohol
Dipeptide aldehyde
Morcelle del Valle, Susana Raquel
Cánepa, Alicia Susana
Padró, Juan Manuel
Llerena Suster, Carlos R.
Clapés, Pere
Syntheses of dipeptide alcohols and dipeptide aldehyde precursors catalyzed by plant cysteine peptidases
topic_facet Biología
Química
Plant peptidases
Coded and no-coded amino acids
Dipeptide alcohol
Dipeptide aldehyde
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.
format Articulo
Articulo
author Morcelle del Valle, Susana Raquel
Cánepa, Alicia Susana
Padró, Juan Manuel
Llerena Suster, Carlos R.
Clapés, Pere
author_facet Morcelle del Valle, Susana Raquel
Cánepa, Alicia Susana
Padró, Juan Manuel
Llerena Suster, Carlos R.
Clapés, Pere
author_sort Morcelle del Valle, Susana Raquel
title Syntheses of dipeptide alcohols and dipeptide aldehyde precursors catalyzed by plant cysteine 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
publishDate 2013
url http://sedici.unlp.edu.ar/handle/10915/153064
work_keys_str_mv AT morcelledelvallesusanaraquel synthesesofdipeptidealcoholsanddipeptidealdehydeprecursorscatalyzedbyplantcysteinepeptidases
AT canepaaliciasusana synthesesofdipeptidealcoholsanddipeptidealdehydeprecursorscatalyzedbyplantcysteinepeptidases
AT padrojuanmanuel synthesesofdipeptidealcoholsanddipeptidealdehydeprecursorscatalyzedbyplantcysteinepeptidases
AT llerenasustercarlosr synthesesofdipeptidealcoholsanddipeptidealdehydeprecursorscatalyzedbyplantcysteinepeptidases
AT clapespere synthesesofdipeptidealcoholsanddipeptidealdehydeprecursorscatalyzedbyplantcysteinepeptidases
_version_ 1766370241286242304

Ejemplares similares