000276452 001__ 276452
000276452 005__ 20210129220905.0
000276452 0247_ $$2doi$$a10.1007/s00216-015-8826-8
000276452 0247_ $$2ISSN$$a0016-1152
000276452 0247_ $$2ISSN$$a0372-7920
000276452 0247_ $$2ISSN$$a0937-0633
000276452 0247_ $$2ISSN$$a1432-1130
000276452 0247_ $$2ISSN$$a1618-2642
000276452 0247_ $$2ISSN$$a1618-2650
000276452 0247_ $$2WOS$$aWOS:000360220800009
000276452 0247_ $$2altmetric$$aaltmetric:4437285
000276452 0247_ $$2pmid$$apmid:26123437
000276452 037__ $$aFZJ-2015-06891
000276452 082__ $$a540
000276452 1001_ $$0P:(DE-Juel1)141687$$aPattky, Martin$$b0
000276452 245__ $$aStructure characterization of unexpected covalent O-sulfonation and ion-pairing on an extremely hydrophilic peptide with CE-MS and FT-ICR-MS
000276452 260__ $$aBerlin$$bSpringer$$c2015
000276452 3367_ $$0PUB:(DE-HGF)16$$2PUB:(DE-HGF)$$aJournal Article$$bjournal$$mjournal$$s1449672882_32507
000276452 3367_ $$2DataCite$$aOutput Types/Journal article
000276452 3367_ $$00$$2EndNote$$aJournal Article
000276452 3367_ $$2BibTeX$$aARTICLE
000276452 3367_ $$2ORCID$$aJOURNAL_ARTICLE
000276452 3367_ $$2DRIVER$$aarticle
000276452 520__ $$aIn this study, we characterized unexpected side-products in a commercially synthesized peptide with the sequence RPRTRLHTHRNR. This so-called peptide D3 was selected by mirror phage display against low molecular weight amyloid-β-peptide (Aβ) associated with Alzheimer’s disease. Capillary electrophoresis (CE) was the method of choice for structure analysis because the extreme hydrophilicity of the peptide did not allow reversed-phase liquid chromatography (RPLC) and hydrophilic interaction stationary phases (HILIC). CE-MS analysis, applying a strongly acidic background electrolyte and different statically adsorbed capillary coatings, provided fast and efficient analysis and revealed that D3 unexpectedly showed strong ion-pairing with sulfuric acid. Moreover, covalent O-sulfonation at one or two threonine residues was identified as a result of a side reaction during peptide synthesis, and deamidation was found at either the asparagine residue or at the C-terminus. In total, more than 10 different species with different m/z values were observed. Tandem-MS analysis with collision induced dissociation (CID) using a CE-quadrupole-time-of-flight (QTOF) setup predominantly resulted in sulfate losses and did not yield any further characteristic fragment ions at high collision energies. Therefore, direct infusion Fourier transform ion cyclotron resonance (FT-ICR) MS was employed to identify the covalent modification and discriminate O-sulfonation from possible O-phosphorylation by using an accurate mass analysis. Electron transfer dissociation (ETD) was used for the identification of the threonine O-sulfation sites. In this work, it is shown that the combination of CE-MS and FT-ICR-MS with ETD fragmentation was essential for the full characterization of this extremely basic peptide with labile modifications.
000276452 536__ $$0G:(DE-HGF)POF3-551$$a551 - Functional Macromolecules and Complexes (POF3-551)$$cPOF3-551$$fPOF III$$x0
000276452 588__ $$aDataset connected to CrossRef
000276452 7001_ $$0P:(DE-HGF)0$$aNicolardi, Simone$$b1
000276452 7001_ $$0P:(DE-Juel1)133853$$aSantiago-Schübel, Beatrix$$b2$$ufzj
000276452 7001_ $$0P:(DE-Juel1)156274$$aSydes, Daniel$$b3
000276452 7001_ $$0P:(DE-HGF)0$$avan der Burgt, Yuri E. M.$$b4
000276452 7001_ $$0P:(DE-Juel1)145785$$aKlein, Antonia N.$$b5$$ufzj
000276452 7001_ $$0P:(DE-Juel1)145884$$aJiang, Nan$$b6$$ufzj
000276452 7001_ $$0P:(DE-Juel1)132012$$aMohrlüder, Jeannine$$b7$$ufzj
000276452 7001_ $$0P:(DE-Juel1)132005$$aHänel, Karen$$b8$$ufzj
000276452 7001_ $$0P:(DE-Juel1)159137$$aKutzsche, Janine$$b9$$ufzj
000276452 7001_ $$0P:(DE-HGF)0$$aFunke, S. A.$$b10
000276452 7001_ $$0P:(DE-Juel1)132029$$aWillbold, D.$$b11$$ufzj
000276452 7001_ $$0P:(DE-Juel1)133857$$aWillbold, S.$$b12$$ufzj
000276452 7001_ $$0P:(DE-Juel1)138805$$aHuhn, C.$$b13$$eCorresponding author
000276452 773__ $$0PERI:(DE-600)1459122-4$$a10.1007/s00216-015-8826-8$$gVol. 407, no. 22, p. 6637 - 6655$$n22$$p6637 - 6655$$tAnalytical and bioanalytical chemistry$$v407$$x0016-1152$$y2015
000276452 8564_ $$uhttp://link.springer.com/article/10.1007%2Fs00216-015-8826-8
000276452 8564_ $$uhttps://juser.fz-juelich.de/record/276452/files/Structure%20characterization%20of%20unexpected%20covalent%20O-sulfonation%20and%20ion-pairing%20on%20an%20extremely%20hydrophilic%20peptide%20with%20CE-MS%20and%20FT-ICR-MS.pdf$$yRestricted
000276452 8564_ $$uhttps://juser.fz-juelich.de/record/276452/files/Structure%20characterization%20of%20unexpected%20covalent%20O-sulfonation%20and%20ion-pairing%20on%20an%20extremely%20hydrophilic%20peptide%20with%20CE-MS%20and%20FT-ICR-MS.gif?subformat=icon$$xicon$$yRestricted
000276452 8564_ $$uhttps://juser.fz-juelich.de/record/276452/files/Structure%20characterization%20of%20unexpected%20covalent%20O-sulfonation%20and%20ion-pairing%20on%20an%20extremely%20hydrophilic%20peptide%20with%20CE-MS%20and%20FT-ICR-MS.jpg?subformat=icon-1440$$xicon-1440$$yRestricted
000276452 8564_ $$uhttps://juser.fz-juelich.de/record/276452/files/Structure%20characterization%20of%20unexpected%20covalent%20O-sulfonation%20and%20ion-pairing%20on%20an%20extremely%20hydrophilic%20peptide%20with%20CE-MS%20and%20FT-ICR-MS.jpg?subformat=icon-180$$xicon-180$$yRestricted
000276452 8564_ $$uhttps://juser.fz-juelich.de/record/276452/files/Structure%20characterization%20of%20unexpected%20covalent%20O-sulfonation%20and%20ion-pairing%20on%20an%20extremely%20hydrophilic%20peptide%20with%20CE-MS%20and%20FT-ICR-MS.jpg?subformat=icon-640$$xicon-640$$yRestricted
000276452 8564_ $$uhttps://juser.fz-juelich.de/record/276452/files/Structure%20characterization%20of%20unexpected%20covalent%20O-sulfonation%20and%20ion-pairing%20on%20an%20extremely%20hydrophilic%20peptide%20with%20CE-MS%20and%20FT-ICR-MS.pdf?subformat=pdfa$$xpdfa$$yRestricted
000276452 909CO $$ooai:juser.fz-juelich.de:276452$$pVDB
000276452 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)133853$$aForschungszentrum Jülich GmbH$$b2$$kFZJ
000276452 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)145785$$aForschungszentrum Jülich GmbH$$b5$$kFZJ
000276452 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)145884$$aForschungszentrum Jülich GmbH$$b6$$kFZJ
000276452 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)132012$$aForschungszentrum Jülich GmbH$$b7$$kFZJ
000276452 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)132005$$aForschungszentrum Jülich GmbH$$b8$$kFZJ
000276452 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)159137$$aForschungszentrum Jülich GmbH$$b9$$kFZJ
000276452 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)132029$$aForschungszentrum Jülich GmbH$$b11$$kFZJ
000276452 9101_ $$0I:(DE-588b)5008462-8$$6P:(DE-Juel1)133857$$aForschungszentrum Jülich GmbH$$b12$$kFZJ
000276452 9131_ $$0G:(DE-HGF)POF3-551$$1G:(DE-HGF)POF3-550$$2G:(DE-HGF)POF3-500$$3G:(DE-HGF)POF3$$4G:(DE-HGF)POF$$aDE-HGF$$bKey Technologies$$lBioSoft – Fundamentals for future Technologies in the fields of Soft Matter and Life Sciences$$vFunctional Macromolecules and Complexes$$x0
000276452 9141_ $$y2015
000276452 915__ $$0StatID:(DE-HGF)0420$$2StatID$$aNationallizenz
000276452 915__ $$0StatID:(DE-HGF)0200$$2StatID$$aDBCoverage$$bSCOPUS
000276452 915__ $$0StatID:(DE-HGF)0300$$2StatID$$aDBCoverage$$bMedline
000276452 915__ $$0StatID:(DE-HGF)0310$$2StatID$$aDBCoverage$$bNCBI Molecular Biology Database
000276452 915__ $$0StatID:(DE-HGF)0100$$2StatID$$aJCR$$bANAL BIOANAL CHEM : 2014
000276452 915__ $$0StatID:(DE-HGF)0199$$2StatID$$aDBCoverage$$bThomson Reuters Master Journal List
000276452 915__ $$0StatID:(DE-HGF)0110$$2StatID$$aWoS$$bScience Citation Index
000276452 915__ $$0StatID:(DE-HGF)0150$$2StatID$$aDBCoverage$$bWeb of Science Core Collection
000276452 915__ $$0StatID:(DE-HGF)0111$$2StatID$$aWoS$$bScience Citation Index Expanded
000276452 915__ $$0StatID:(DE-HGF)1150$$2StatID$$aDBCoverage$$bCurrent Contents - Physical, Chemical and Earth Sciences
000276452 915__ $$0StatID:(DE-HGF)1050$$2StatID$$aDBCoverage$$bBIOSIS Previews
000276452 915__ $$0StatID:(DE-HGF)9900$$2StatID$$aIF < 5
000276452 920__ $$lyes
000276452 9201_ $$0I:(DE-Juel1)ICS-6-20110106$$kICS-6$$lStrukturbiochemie $$x0
000276452 980__ $$ajournal
000276452 980__ $$aVDB
000276452 980__ $$aI:(DE-Juel1)ICS-6-20110106
000276452 980__ $$aUNRESTRICTED
000276452 981__ $$aI:(DE-Juel1)IBI-7-20200312