Synthetic strategies for efficient conjugation of organometallic complexes with pendant protein reactive markers

Handle URI:
http://hdl.handle.net/10754/563063
Title:
Synthetic strategies for efficient conjugation of organometallic complexes with pendant protein reactive markers
Authors:
Jantke, Dominik; Marziale, Alexander N.; Reiner, Thomas; Kraus, Florian; Herdtweck, Eberhardt; Raba, Andreas; Eppinger, Jorg ( 0000-0001-7886-7059 )
Abstract:
Site-directed conjugation of metal centers to proteins is fundamental for biological and bioinorganic applications of transition metals. However, methods for the site-selective introduction of metal centers remain scarce. Herein, we present broadly applicable synthetic strategies for the conjugation of bioactive molecules with a range of organometallic complexes. Following three different synthetic strategies, we were able to synthesize a small library of metal conjugated protein markers featuring different types of protein reactive sites (epoxides, phenylphosphonates, fluorosulfonates and fluorophosphonate groups) as well as different late transition metals (iron, ruthenium, rhodium, palladium and platinum). The products were isolated in moderate to excellent yields and high purity. Furthermore, X-ray diffraction of the metalated protein markers corroborates structural integrity of the metal complex and the protein reactive site. © 2013 Elsevier B.V. All rights reserved.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division; Chemical Science Program; Biological & Organometallic Catalysis Laboratories
Publisher:
Elsevier BV
Journal:
Journal of Organometallic Chemistry
Issue Date:
Nov-2013
DOI:
10.1016/j.jorganchem.2013.05.027
Type:
Article
ISSN:
0022328X
Sponsors:
The authors thank Ramona Lex for help with crystallization. This work was supported by KAUST-GCR (FIC/2010/07) and the KAUST baseline fund (J.E.). We also thank the Elitenetzwerk Bayern for graduate fellowships for T.R. and A.N.M.
Is Supplemented By:
Jantke, D., Marziale, A. N., Reiner, T., Kraus, F., Herdtweck, E., Raba, A., & Eppinger, J. (2013). CCDC 929468: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1065v7; DOI:10.5517/cc1065v7; HANDLE:http://hdl.handle.net/10754/624198; Jantke, D., Marziale, A. N., Reiner, T., Kraus, F., Herdtweck, E., Raba, A., & Eppinger, J. (2013). CCDC 868620: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccy4w0y; DOI:10.5517/ccy4w0y; HANDLE:http://hdl.handle.net/10754/624685
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorJantke, Dominiken
dc.contributor.authorMarziale, Alexander N.en
dc.contributor.authorReiner, Thomasen
dc.contributor.authorKraus, Florianen
dc.contributor.authorHerdtweck, Eberhardten
dc.contributor.authorRaba, Andreasen
dc.contributor.authorEppinger, Jorgen
dc.date.accessioned2015-08-03T11:34:56Zen
dc.date.available2015-08-03T11:34:56Zen
dc.date.issued2013-11en
dc.identifier.issn0022328Xen
dc.identifier.doi10.1016/j.jorganchem.2013.05.027en
dc.identifier.urihttp://hdl.handle.net/10754/563063en
dc.description.abstractSite-directed conjugation of metal centers to proteins is fundamental for biological and bioinorganic applications of transition metals. However, methods for the site-selective introduction of metal centers remain scarce. Herein, we present broadly applicable synthetic strategies for the conjugation of bioactive molecules with a range of organometallic complexes. Following three different synthetic strategies, we were able to synthesize a small library of metal conjugated protein markers featuring different types of protein reactive sites (epoxides, phenylphosphonates, fluorosulfonates and fluorophosphonate groups) as well as different late transition metals (iron, ruthenium, rhodium, palladium and platinum). The products were isolated in moderate to excellent yields and high purity. Furthermore, X-ray diffraction of the metalated protein markers corroborates structural integrity of the metal complex and the protein reactive site. © 2013 Elsevier B.V. All rights reserved.en
dc.description.sponsorshipThe authors thank Ramona Lex for help with crystallization. This work was supported by KAUST-GCR (FIC/2010/07) and the KAUST baseline fund (J.E.). We also thank the Elitenetzwerk Bayern for graduate fellowships for T.R. and A.N.M.en
dc.publisherElsevier BVen
dc.subjectBioinorganic chemistryen
dc.subjectMetalloenzymesen
dc.subjectPeptide couplingen
dc.subjectProtease inhibitorsen
dc.titleSynthetic strategies for efficient conjugation of organometallic complexes with pendant protein reactive markersen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentBiological & Organometallic Catalysis Laboratoriesen
dc.identifier.journalJournal of Organometallic Chemistryen
dc.contributor.institutionDepartment Chemie, Technische Universität München, Lichtenbergstr. 4, D-85747 Garching bei München, Germanyen
dc.contributor.institutionDepartment of Radiology, Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, New York, NY 10065, United Statesen
kaust.authorEppinger, Jorgen
kaust.authorJantke, Dominiken
kaust.authorMarziale, Alexander N.en
kaust.authorReiner, Thomasen
dc.relation.isSupplementedByJantke, D., Marziale, A. N., Reiner, T., Kraus, F., Herdtweck, E., Raba, A., & Eppinger, J. (2013). CCDC 929468: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc1065v7en
dc.relation.isSupplementedByDOI:10.5517/cc1065v7en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624198en
dc.relation.isSupplementedByJantke, D., Marziale, A. N., Reiner, T., Kraus, F., Herdtweck, E., Raba, A., & Eppinger, J. (2013). CCDC 868620: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccy4w0yen
dc.relation.isSupplementedByDOI:10.5517/ccy4w0yen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624685en
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