Chromatographic Behavior of Peptides Containing Oxidized Methionine in Reversed-phase Chromatography: Application to Cyclolinopeptides in Flaxseed Oil and Linear Tryptic Peptides

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dc.contributor.authorLao, Ying
dc.contributor.examiningcommitteePerreault, Helene (Chemistry) O'Neil, Joe (Chemistry) Aliani, Michel (Human Nutritional Science)en_US
dc.contributor.supervisorKrokhine, Oleg (Chemistry)en_US
dc.date.accessioned2015-01-13T14:55:02Z
dc.date.available2015-01-13T14:55:02Z
dc.date.issued2012en_US
dc.date.issued2014en_US
dc.degree.disciplineChemistryen_US
dc.degree.levelMaster of Science (M.Sc.)en_US
dc.description.abstractThe thesis consists of two parts targeting the characterization of chromatographic behavior of linear tryptic and cyclic peptides containing oxidized methionine (Met) in reversed-phased chromatography. The retention order of methionine-containing peptide analogues was observed to be the same in both studies: Met oxide < Met dioxide < Met. For linear tryptic peptides, the magnitude of the retention time shift may vary dramatically: from –9 % to +0.36 % acetonitrile. Particularly, large negative retention time shifts are found mostly associated with methionine being in the hydrophobic face of an amphipathic helix. Contrary to previously reported observations, I demonstrate for the first time that methionine oxidation may increase peptide hydrophobicity, this occurs only when methionine is in the N3 position of the N-capping stabilization motif preceding an amphipathic helix. In the second study, the effect of peak splitting was observed for some Met oxide-containing cyclolinopeptides, which most likely appear due to diastereomerization.en_US
dc.description.noteFebruary 2015en_US
dc.identifier.citationJ. Reimer, V. Spicer, O.V. Krokhin, J Chromatogr A 1256 (2012) 160en_US
dc.identifier.citationY.W. Lao, K. Mackenzie, W. Vincent, O.V. Krokhin, Journal of Separation Science 37 (2014), 1788-1796.en_US
dc.identifier.urihttp://hdl.handle.net/1993/30202
dc.language.isoengen_US
dc.publisherElsevieren_US
dc.publisherJohn Wiley and Sonsen_US
dc.rightsopen accessen_US
dc.subjectMethionine Oxidationen_US
dc.subjectReversed-phase chromatographyen_US
dc.subjecttryptic peptidesen_US
dc.subjectcyclolinopeptidesen_US
dc.titleChromatographic Behavior of Peptides Containing Oxidized Methionine in Reversed-phase Chromatography: Application to Cyclolinopeptides in Flaxseed Oil and Linear Tryptic Peptidesen_US
dc.typemaster thesisen_US
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