A new synthesis of peptidyl epoxysuccinates for probing cysteine protease-inhibitor P3/S3 binding interactions

William R. Roush; Alejandro Alvarez Hernandez; Gerardo Zepeda

doi:10.1055/s-1999-3648

A new synthesis of peptidyl epoxysuccinates for probing cysteine protease-inhibitor P₃/S₃ binding interactions

William R. Roush, Alejandro Alvarez Hernandez, Gerardo Zepeda

Producción científica: Contribución a una revista › Artículo › revisión exhaustiva

8 Citas (Scopus)

Resumen

A new synthesis of peptidyl epoxysuccinates has been developed involving the N-acylation of amino acid benzyl esters (12) with the tartrate ester derived epoxy acid 13 followed by deprotection of the benzyl esters and acylation with amines 21-28. This synthesis is ideally suited for the rapid synthesis of peptidyl epoxysuccinate inhibitors of cysteine proteases, in order to probe selectivity issues concerning inhibitor/enzyme P₃/S₃ binding interactions.

Idioma original	Inglés
Páginas (desde-hasta)	1500-1504
Número de páginas	5
Publicación	Synthesis (Germany)
N.º	SPEC. ISS.
DOI	https://doi.org/10.1055/s-1999-3648
Estado	Publicada - 1999
Publicado de forma externa	Sí

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abstract = "A new synthesis of peptidyl epoxysuccinates has been developed involving the N-acylation of amino acid benzyl esters (12) with the tartrate ester derived epoxy acid 13 followed by deprotection of the benzyl esters and acylation with amines 21-28. This synthesis is ideally suited for the rapid synthesis of peptidyl epoxysuccinate inhibitors of cysteine proteases, in order to probe selectivity issues concerning inhibitor/enzyme P3/S3 binding interactions.",

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AU - Hernandez, Alejandro Alvarez

AU - Zepeda, Gerardo

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N2 - A new synthesis of peptidyl epoxysuccinates has been developed involving the N-acylation of amino acid benzyl esters (12) with the tartrate ester derived epoxy acid 13 followed by deprotection of the benzyl esters and acylation with amines 21-28. This synthesis is ideally suited for the rapid synthesis of peptidyl epoxysuccinate inhibitors of cysteine proteases, in order to probe selectivity issues concerning inhibitor/enzyme P3/S3 binding interactions.

AB - A new synthesis of peptidyl epoxysuccinates has been developed involving the N-acylation of amino acid benzyl esters (12) with the tartrate ester derived epoxy acid 13 followed by deprotection of the benzyl esters and acylation with amines 21-28. This synthesis is ideally suited for the rapid synthesis of peptidyl epoxysuccinate inhibitors of cysteine proteases, in order to probe selectivity issues concerning inhibitor/enzyme P3/S3 binding interactions.

KW - Cysteine protease inhibitors

KW - E-64 analogs

KW - Peptide synthesis

KW - Peptidyl epoxysuccinates

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U2 - 10.1055/s-1999-3648

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M3 - Artículo

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