Phenylalanine-a biogenic ligand with flexible η6- and η6:κ1-coordination at ruthenium(ii) centres

Handle URI:
http://hdl.handle.net/10754/562506
Title:
Phenylalanine-a biogenic ligand with flexible η6- and η6:κ1-coordination at ruthenium(ii) centres
Authors:
Reiner, Thomas; Jantke, Dominik; Miao, Xiaohe; Marziale, Alexander N.; Kiefer, Florian J.; Eppinger, Jorg ( 0000-0001-7886-7059 )
Abstract:
The reaction of (S)-2,5-dihydrophenylalanine 1 with ruthenium(iii) chloride yields the μ-chloro-bridged dimeric η6-phenylalanine ethyl ester complex 3, which can be converted into the monomeric analogue, η6:κ1-phenylalanine ethyl ester complex 12, under basic conditions. Studies were carried out to determine the stability and reactivity of complexes bearing η6- and η6: κ1-chelating phenylalanine ligands under various conditions. Reaction of 3 with ethylenediamine derivatives N-p-tosylethylenediamine or 1,4-di-N-p-tosylethylenediamine results in the formation of monomeric η6:κ1-phenylalanine ethyl ester complexes 14 and 15, which could be saponified yielding complexes 16 and 17 without changing the inner coordination sphere of the metal centre. The structure of η6:κ1-phenylalanine complex 17 and an N-κ1-phenylalanine complex 13 resulting from the reaction of 3 with an excess of pyridine were confirmed by X-ray crystallography. © 2013 The Royal Society of Chemistry.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division; Chemical Science Program; Biological & Organometallic Catalysis Laboratories
Publisher:
Royal Society of Chemistry (RSC)
Journal:
Dalton Transactions
Issue Date:
2013
DOI:
10.1039/c3dt50589h
PubMed ID:
23632736
Type:
Article
ISSN:
14779226
Sponsors:
The authors thank Dr Andreas O. Frank for help with NMR spectra and both Prof. Dr Horst Kessler and Prof. Dr Thomas F. Fassler for helpful discussions. This work was supported by KAUST-GCR (FIC/2010/07) and the KAUST baseline fund (J. E.). We thank the Elitenetzwerk Bayern (graduate fellowship for T. R. and A. N. M.) and the IDK NanoCat for funding.
Is Supplemented By:
Reiner, T., Jantke, D., Miao, X.-H., Marziale, A. N., Kiefer, F. J., & Eppinger, J. (2013). CCDC 721713: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccs7022; DOI:10.5517/ccs7022; HANDLE:http://hdl.handle.net/10754/624608; Reiner, T., Jantke, D., Miao, X.-H., Marziale, A. N., Kiefer, F. J., & Eppinger, J. (2013). CCDC 721712: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccs7011; DOI:10.5517/ccs7011; HANDLE:http://hdl.handle.net/10754/624607
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.authorReiner, Thomasen
dc.contributor.authorJantke, Dominiken
dc.contributor.authorMiao, Xiaoheen
dc.contributor.authorMarziale, Alexander N.en
dc.contributor.authorKiefer, Florian J.en
dc.contributor.authorEppinger, Jorgen
dc.date.accessioned2015-08-03T10:40:38Zen
dc.date.available2015-08-03T10:40:38Zen
dc.date.issued2013en
dc.identifier.issn14779226en
dc.identifier.pmid23632736en
dc.identifier.doi10.1039/c3dt50589hen
dc.identifier.urihttp://hdl.handle.net/10754/562506en
dc.description.abstractThe reaction of (S)-2,5-dihydrophenylalanine 1 with ruthenium(iii) chloride yields the μ-chloro-bridged dimeric η6-phenylalanine ethyl ester complex 3, which can be converted into the monomeric analogue, η6:κ1-phenylalanine ethyl ester complex 12, under basic conditions. Studies were carried out to determine the stability and reactivity of complexes bearing η6- and η6: κ1-chelating phenylalanine ligands under various conditions. Reaction of 3 with ethylenediamine derivatives N-p-tosylethylenediamine or 1,4-di-N-p-tosylethylenediamine results in the formation of monomeric η6:κ1-phenylalanine ethyl ester complexes 14 and 15, which could be saponified yielding complexes 16 and 17 without changing the inner coordination sphere of the metal centre. The structure of η6:κ1-phenylalanine complex 17 and an N-κ1-phenylalanine complex 13 resulting from the reaction of 3 with an excess of pyridine were confirmed by X-ray crystallography. © 2013 The Royal Society of Chemistry.en
dc.description.sponsorshipThe authors thank Dr Andreas O. Frank for help with NMR spectra and both Prof. Dr Horst Kessler and Prof. Dr Thomas F. Fassler for helpful discussions. This work was supported by KAUST-GCR (FIC/2010/07) and the KAUST baseline fund (J. E.). We thank the Elitenetzwerk Bayern (graduate fellowship for T. R. and A. N. M.) and the IDK NanoCat for funding.en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.titlePhenylalanine-a biogenic ligand with flexible η6- and η6:κ1-coordination at ruthenium(ii) centresen
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.journalDalton Transactionsen
dc.contributor.institutionTechnische Universität München, Department Chemie, Lichtenbergstr. 4, D-85747 Garching, Germanyen
dc.contributor.institutionDepartment of Radiology, Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, New York, NY 10065, United Statesen
kaust.authorMiao, Xiaoheen
kaust.authorEppinger, Jorgen
kaust.authorJantke, Dominiken
kaust.authorMarziale, Alexander N.en
dc.relation.isSupplementedByReiner, T., Jantke, D., Miao, X.-H., Marziale, A. N., Kiefer, F. J., & Eppinger, J. (2013). CCDC 721713: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccs7022en
dc.relation.isSupplementedByDOI:10.5517/ccs7022en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624608en
dc.relation.isSupplementedByReiner, T., Jantke, D., Miao, X.-H., Marziale, A. N., Kiefer, F. J., & Eppinger, J. (2013). CCDC 721712: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccs7011en
dc.relation.isSupplementedByDOI:10.5517/ccs7011en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624607en

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