Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/4568
DC FieldValueLanguage
dc.contributor.authorM., Demarcusen_us
dc.contributor.authorM. L., Ganaduen_us
dc.contributor.authorG. M., Muraen_us
dc.contributor.authorA., Porchedduen_us
dc.contributor.authorL., Quarantaen_us
dc.contributor.authorG., Reginatoen_us
dc.contributor.authorTaddei, Maurizioen_us
dc.date.accessioned2021-03-30T15:43:06Z-
dc.date.available2021-03-30T15:43:06Z-
dc.date.issued2001-
dc.identifier.issn0022-3263en_US
dc.identifier.urihttp://hdl.handle.net/20.500.12779/4568-
dc.description45990en_US
dc.description.abstractDifferent 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.en_US
dc.language.isoenen_US
dc.relationNoneen_US
dc.relation.ispartofJOURNAL OF ORGANIC CHEMISTRYen_US
dc.titleSmall ring constrained peptidomimetics. Synthesis of epoxy peptidomimetics, inhibitors of cysteine proteasesen_US
dc.typeArticleen_US
dc.identifier.doi10.1021/jo000961wen_US
dc.identifier.scopus2-s2.0-0035830510en_US
dc.identifier.isiWOS:000166943800009en_US
dc.relation.volume66en_US
dc.description.firstpage697en_US
dc.description.lastpage706en_US
dc.description.thirdmissionNot applicableen_US
item.cerifentitytypePublications-
item.grantfulltextnone-
item.languageiso639-1en-
item.openairecristypehttp://purl.org/coar/resource_type/c_18cf-
item.openairetypeArticle-
item.fulltextNo Fulltext-
crisitem.author.orcid0000-0001-8660-7580-
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