New Fluorous Photoaffinity Labels (F-PAL) and Their Application in V-ATPase Inhibition Studies

DC FieldValueLanguage
dc.contributor.authorBurkard, Nadja
dc.contributor.authorBender, Tobias
dc.contributor.authorWestmeier, Johannes
dc.contributor.authorNordmann, Christin
dc.contributor.authorHuss, Markus
dc.contributor.authorWieczorek, Helmut
dc.contributor.authorGrond, Stephanie
dc.contributor.authorvon Zezschwitz, Paultheo
dc.date.accessioned2021-12-23T16:16:19Z-
dc.date.available2021-12-23T16:16:19Z-
dc.date.issued2010
dc.identifier.issn1434193X
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/11814-
dc.description.abstract(Trifluoromethyl)diazirines are well established photoaffinity labels (PAL) used in biochemical investigations to create covalent ligand-receptor bonds. Two new diazirinylbenzoic acids 8b,c with perfluorobutyl and perfluorooctyl chains (F-PAL) were efficiently prepared from p-bromobenzaldehyde and attached to the highly potent and specific V-ATPase inhibitors 21-deoxyconcanolide A (2) and bafilomycin A(1) (5), deriving from the natural product pool from Streptomyces producer strains. The labelled derivatives 17 and 18 were efficiently purified by fluorous solid-phase extraction. Functional biochemical assays with the V-ATPase holoenzymes proofed strong inhibition activities. So far, radioactive isotopes or biotin-tags have mainly been used for tracing compounds in photoaffinity studies. The C4F9- and C8F17-fluorous tags aim to enable advantageous separation and identification of labelled peptide fragments by fluorous chromatography followed by MS analysis. Therefore, F-PAL represents an innovative new concept for binding site determination and should significantly accelerate and simplify such biochemical investigations.
dc.description.sponsorshipBundesministerium fur Bildung und ForschungFederal Ministry of Education & Research (BMBF); Otto Romer Stiftung; Deutsche Forschungsgemeinschaft (DFG)German Research Foundation (DFG) [SFB 431]; This work was financially supported by the Bundesministerium fur Bildung und Forschung (GenoMik+: MetabolitGenoMik) and the Otto Romer Stiftung (to S. G.) as well as the Deutsche Forschungsgemeinschaft (DFG) (SFB 431, to H. W., M. H.). Thanks go to Hans-Jorg Langer (from S. G.) for excellent technical assistance and his prolific scientific encouragement and ideas and to Bastian Weinert (from P. Z.) for preparation of compound 8c. H. W. and M. H. thank Martin Dransmann for his excellent technical assistance in purifying the V-ATPase.
dc.language.isoen
dc.publisherWILEY-V C H VERLAG GMBH
dc.relation.ispartofEUROPEAN JOURNAL OF ORGANIC CHEMISTRY
dc.subjectACID
dc.subjectBafilomycin
dc.subjectBAFILOMYCIN/CONCANAMYCIN-BINDING-SITE
dc.subjectChemistry
dc.subjectChemistry, Organic
dc.subjectConcanamycin
dc.subjectCONCANAMYCIN-A
dc.subjectFluorous chromatography
dc.subjectP-TYPE
dc.subjectPerfluorinated reagents
dc.subjectPhotoaffinity labeling
dc.subjectSUBUNIT-C
dc.subjectV-ATPase inhibitors
dc.subjectVACUOLAR ATPASE
dc.titleNew Fluorous Photoaffinity Labels (F-PAL) and Their Application in V-ATPase Inhibition Studies
dc.typejournal article
dc.identifier.doi10.1002/ejoc.200901463
dc.identifier.isiISI:000277214000015
dc.description.volume2010
dc.description.issue11
dc.description.startpage2176
dc.description.endpage2181
dc.identifier.eissn10990690
dc.publisher.placePOSTFACH 101161, 69451 WEINHEIM, GERMANY
dcterms.isPartOf.abbreviationEur. J. Org. Chem.
crisitem.author.deptUniversität Osnabrück-
crisitem.author.deptFB 05 - Biologie/Chemie-
crisitem.author.deptidfb05-
crisitem.author.parentorgUniversität Osnabrück-
crisitem.author.netidHuMa001-
crisitem.author.netidWiHe990-
Show simple item record

Page view(s)

3
Last Week
0
Last month
0
checked on May 20, 2024

Google ScholarTM

Check

Altmetric