Document Detail

Small ring constrained peptidomimetics. Synthesis of epoxy peptidomimetics, inhibitors of cysteine proteases.
MedLine Citation:
PMID:  11430085     Owner:  NLM     Status:  MEDLINE    
Different dipeptide analogues containing an oxirane ring in the place of the peptidic bond were prepared starting from naturally occurring amino acids. N-Fmoc-amino aldehydes were transformed into the corresponding methoxyvinyl derivatives through a Wittig reaction, and the addition of PhSeCl gave a series of different alpha-phenylselenyl aldehydes. Mukajiama reaction with silylketene acetals gave an intermediate product that was finally transformed into the desired oxiranyl peptidomimetics. Following this strategy we were able to control three new contiguous stereocenters starting from the enantiomerically pure amino acid. The dipeptide analogues could be used in SPPS on a SASRIN resin as the final epoxides were relatively unstable under acidic conditions. Moreover the synthesis of the single dipeptide mimetics was carried out on solid phase to generate a small library of epoxy peptidomimetics. Some of the products prepared in this work resulted as time-dependent reversible inhibitors of cysteine protease.
M Demarcus; M L Ganadu; G M Mura; A Porcheddu; L Quaranta; G Reginato; M Taddei
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  66     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2001 Feb 
Date Detail:
Created Date:  2001-06-29     Completed Date:  2001-08-02     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  697-706     Citation Subset:  IM    
Dipartimento di Chimica, Università degli Studi di Sassari, Via Vienna 2, 07100 Sassari, Italy.
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MeSH Terms
Cysteine Proteinase Inhibitors / chemistry*,  pharmacology
Epoxy Compounds / chemistry*
Magnetic Resonance Spectroscopy
Molecular Mimicry*
Peptides / chemistry*,  pharmacology
Reg. No./Substance:
0/Cysteine Proteinase Inhibitors; 0/Epoxy Compounds; 0/Peptides

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