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dc.contributor.authorKrasavin, Mikhail
dc.contributor.authorBushkova, Ekaterina
dc.contributor.authorParchinsky, Vladislav
dc.contributor.authorShumsky, Alexei
dc.date.accessioned2017-05-03T15:58:33Z
dc.date.available2017-05-03T15:58:33Z
dc.date.issued2010
dc.date.modified2013-05-30T04:33:59Z
dc.identifier.issn0039-7881
dc.identifier.doi10.1055/s-0029-1219274
dc.identifier.urihttp://hdl.handle.net/10072/48042
dc.description.abstractA number of Na-alkyl,N߭acylhydrazines have been synthesized via the Ugi reaction of N-acylhydrazones with an isocyanide and trifluoroacetic acid. The trifluoroacetic acid acted as a 'silent partner' and becomes removed upon basic workup of the reaction. These compounds have been efficiently modified further via reductive alkylation to produce Na,Na-dialkyl,N߭acylhydrazines. The two groups of novel hydrazinopeptide motifs have been shown by simple 鈠NMR spectroscopic experiments to display two different secondary structure patterns. These observations were confirmed by X-ray crystallographic analysis. Combining the hydrazone and carboxylic acid moieties in one reaction precursor offers the opportunity for an 'intramolecular' hydrazino-Ugi reaction, which was also demonstrated.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.format.extent232680 bytes
dc.format.mimetypeapplication/pdf
dc.languageEnglish
dc.language.isoeng
dc.publisherGeorg Thieme Verlag
dc.publisher.placeGermany
dc.relation.ispartofstudentpublicationY
dc.relation.ispartofpagefrom0933
dc.relation.ispartofpageto0942
dc.relation.ispartofjournalSynthesis
dc.relation.ispartofvolume6
dc.rights.retentionN
dc.subject.fieldofresearchOrganic Chemical Synthesis
dc.subject.fieldofresearchAnalytical Chemistry
dc.subject.fieldofresearchOrganic Chemistry
dc.subject.fieldofresearchcode030503
dc.subject.fieldofresearchcode0301
dc.subject.fieldofresearchcode0305
dc.titleHydrazinopeptide Motifs Synthesized via the Ugi Reaction: An Insight into the Secondary Structure
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.rights.copyright© 2010 Georg Thieme Verlag. This is the author-manuscript version of the paper. Reproduced in accordance with the copyright policy of the publisher. The definitive version is available at www.thieme-connect.com
gro.date.issued2010
gro.hasfulltextFull Text
gro.griffith.authorKrasavin, Mikhail


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