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

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

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.

Original language	English
Pages (from-to)	1500-1504
Number of pages	5
Journal	Synthesis (Germany)
Issue number	SPEC. ISS.
DOIs	https://doi.org/10.1055/s-1999-3648
State	Published - 1999
Externally published	Yes

Keywords

Cysteine protease inhibitors
E-64 analogs
Peptide synthesis
Peptidyl epoxysuccinates

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10.1055/s-1999-3648

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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

PY - 1999

Y1 - 1999

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

UR - http://www.scopus.com/inward/record.url?scp=0032776064&partnerID=8YFLogxK

U2 - 10.1055/s-1999-3648

DO - 10.1055/s-1999-3648

M3 - Artículo

SN - 0039-7881

SP - 1500

EP - 1504

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - SPEC. ISS.

ER -

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

Abstract

Keywords

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