| Attributs | Valeurs |
|---|
| type
| |
| Is Part Of
| |
| Subject
| |
| Title
| - Small Ring Constrained Peptidomimetics. Synthesis of EpoxyPeptidomimetics, Inhibitors of Cysteine Proteases
|
| has manifestation of work
| |
| related by
| |
| Author
| |
| Abstract
| - Different dipeptide analogues containing an oxirane ring in the place of the peptidic bond wereprepared starting from naturally occurring amino acids. N-Fmoc-amino aldehydes were transformedinto the corresponding methoxyvinyl derivatives through a Wittig reaction, and the addition ofPhSeCl gave a series of different α-phenylselenyl aldehydes. Mukajiama reaction with silylketeneacetals gave an intermediate product that was finally transformed into the desired oxiranylpeptidomimetics. Following this strategy we were able to control three new contiguous stereocentersstarting from the enantiomerically pure amino acid. The dipeptide analogues could be used in SPPSon a SASRIN resin as the final epoxides were relatively unstable under acidic conditions. Moreoverthe synthesis of the single dipeptide mimetics was carried out on solid phase to generate a smalllibrary of epoxy peptidomimetics. Some of the products prepared in this work resulted as time-dependent reversible inhibitors of cysteine protease.
|
| article type
| |
| is part of this journal
| |
