Document Detail

Novel peptide-based pepsin inhibitors containing an epoxide group.
MedLine Citation:
PMID:  18569339     Owner:  NLM     Status:  MEDLINE    
1,2-Epoxy-3-(p-nitrophenoxy)propane (EPNP) is known to inhibit pepsin A and other aspartic proteinases by reacting with the active site aspartic acid residue(s). However, the reaction is considerably slow in general, and therefore, it is desirable to develop similar reagents that are capable of inhibiting these enzymes more rapidly. In the present study, we synthesized a series of novel inhibitors which have a reactive epoxide group linked with peptide by a hydrazide bond, with a general structure: Iva-L-Val-L-Val-(L-AA)(n)-N2H2-ES-OEt (n = 0 approximately 2) (Iva, isovaleryl; AA, bulky hydrophobic or aromatic amino acid residue; ES, epoxysuccinyl). These inhibitors were shown to inhibit porcine pepsin A remarkably faster than EPNP.
Hisashi Ito; Tomoko Hirono; Yusuke Morita; Yoshitaka Nemoto; Yong-Tae Kim; Kenji Takahashi
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of enzyme inhibition and medicinal chemistry     Volume:  23     ISSN:  1475-6374     ISO Abbreviation:  J Enzyme Inhib Med Chem     Publication Date:  2008 Jun 
Date Detail:
Created Date:  2008-06-23     Completed Date:  2008-09-08     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101150203     Medline TA:  J Enzyme Inhib Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  352-6     Citation Subset:  IM    
Department of Chemistry, Faculty of Science and Engineering, Aoyama Gakuin University, Sagamihara, Kanagawa, Japan.
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MeSH Terms
Epoxy Compounds / chemistry,  pharmacology*
Molecular Structure
Pepsin A / antagonists & inhibitors*
Peptides / chemistry,  pharmacology*
Protease Inhibitors / chemistry*,  pharmacology
Structure-Activity Relationship
Reg. No./Substance:
0/Epoxy Compounds; 0/Peptides; 0/Protease Inhibitors; EC A

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