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

Thomas Reiner; Dominik Jantke; Xiaohe Miao; Alexander N. Marziale; Florian J. Kiefer; Jörg Eppinger

doi:10.1039/c3dt50589h

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

Thomas Reiner, Dominik Jantke, Xiaohe Miao, Alexander N. Marziale, Florian J. Kiefer, Jörg Eppinger

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

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.

Original language	English (US)
Pages (from-to)	8692
Journal	Dalton Transactions
Volume	42
Issue number	24
DOIs	https://doi.org/10.1039/c3dt50589h
State	Published - 2013

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledged KAUST grant number(s): FIC/2010/07
Acknowledgements: 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.

ASJC Scopus subject areas

Inorganic Chemistry

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10.1039/c3dt50589h

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

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. {\textcopyright} 2013 The Royal Society of Chemistry.",

author = "Thomas Reiner and Dominik Jantke and Xiaohe Miao and Marziale, {Alexander N.} and Kiefer, {Florian J.} and J{\"o}rg Eppinger",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): FIC/2010/07 Acknowledgements: 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.",

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AU - Marziale, Alexander N.

AU - Kiefer, Florian J.

AU - Eppinger, Jörg

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledged KAUST grant number(s): FIC/2010/07 Acknowledgements: 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.

PY - 2013

Y1 - 2013

N2 - 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.

AB - 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.

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JF - Dalton Transactions

IS - 24

ER -

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

Abstract

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CCDC 721713: Experimental Crystal Structure Determination : Dichloro-(ethyl phenylalaninate)-tris(pyridine)-ruthenium(ii)

CCDC 721712: Experimental Crystal Structure Determination : (N-(2-Aminoethyl)-4-methylbenzenesulfonamidato)-(phenylalaninato)-ruthenium dimethylsulfoxide solvate

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

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 721713: Experimental Crystal Structure Determination : Dichloro-(ethyl phenylalaninate)-tris(pyridine)-ruthenium(ii)

CCDC 721712: Experimental Crystal Structure Determination : (N-(2-Aminoethyl)-4-methylbenzenesulfonamidato)-(phenylalaninato)-ruthenium dimethylsulfoxide solvate

Cite this