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dc.contributor.authorTheodorou, V.en
dc.contributor.authorTroganis, A. N.en
dc.contributor.authorGerothanassis, I. P.en
dc.date.accessioned2015-11-24T16:43:10Z-
dc.date.available2015-11-24T16:43:10Z-
dc.identifier.issn0040-4039-
dc.identifier.urihttps://olympias.lib.uoi.gr/jspui/handle/123456789/8660-
dc.rightsDefault Licence-
dc.subjecto-17 nmren
dc.subjecto-17-labelled amino acid derivativesen
dc.subjectdmsoen
dc.subjecthydrogen boildingen
dc.subjectdimethyl-sulfoxideen
dc.subjectproton-transferen
dc.subjectbenzoic-aciden
dc.subjectaqueous-solutionen
dc.subjectacetic-aciden
dc.subjectl-prolineen
dc.subject303.15 ken
dc.subjectmethanolen
dc.subjectexchangeen
dc.subjectmixturesen
dc.titleOn the detection of both carbonyl and hydroxyl oxygens in amino acid derivatives: a O-17 NMR reinvestigationen
heal.typejournalArticle-
heal.type.enJournal articleen
heal.type.elΆρθρο Περιοδικούel
heal.identifier.primaryDOI 10.1016/j.tetlet.2003.12.162-
heal.identifier.secondary<Go to ISI>://000189233200050-
heal.identifier.secondaryhttp://ac.els-cdn.com/S0040403904000802/1-s2.0-S0040403904000802-main.pdf?_tid=19735290-3247-11e3-a1c2-00000aacb360&acdnat=1381476850_54408ca894561d82a93ba6b700595a00-
heal.languageen-
heal.accesscampus-
heal.recordProviderΠανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείαςel
heal.publicationDate2004-
heal.abstractThe hypothesis and the conclusions of previous O-17 NMR studies on the detection of both oxygens of the carboxylic group of Boc-[O-17]Tyr(2,6-diClBzl)-OH in DMSO-d(6) solution (V. Tsikaris et al., Tetrahedron Lett. 2000, 41, 8651) are reconsidered. The appearance of two discrete resonances at 340 and 175 ppm of this protected amino acid is not now attributed: (a) to the reduction of the intramolecular conformational exchange rate, due to the effect of intramolecular hydrogen bonding of the hydroxy part of the carboxyl with the carbonyl oxygen of the Boc-group, and (b) to the effect of solvent viscosity, suggested in the mentioned study. The cause of this phenomenon is now attributed to a strong hydrogen bonding of the polar proton acceptor solvent DMSO with the carboxy group, which effectively reduces the proton exchange rate, thus becoming slow on the O-17 NMR time scale. (C) 2004 Elsevier Ltd. All rights reserved.en
heal.publisherElsevieren
heal.journalNameTetrahedron Letten
heal.journalTypepeer reviewed-
heal.fullTextAvailabilityTRUE-
Appears in Collections:Άρθρα σε επιστημονικά περιοδικά ( Ανοικτά). ΧΗΜ

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