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Issue 18, 1998
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Structural characterisation and bioconjugation of an active ester containing oxorhenium(V) complex incorporating a thioether donor

Abstract

A simple new 2,3,5,6-tetrafluorophenyl ester containing diamide–thioether–thiol bifunctional chelating agent LH3, HS(CH2)2SCH2C(O)NHCH2C(O)NH(CH2)3C(O)OC6HF4, has been synthesised. The key intermediates were prepared using standard peptide chemistry procedures. Reaction of LH3 with [Bu4N][ReOCl4] formed an uncharged oxorhenium(V) complex, which was characterised by X-ray structural analysis. The five-co-ordinate complex showed approximately square-pyramidal geometry with an apical oxo group and a basal ligand set comprising a deprotonated thiol group, two deprotonated amide groups, and a thioether group. A second complex of stoichiometry [ReO(LH2)2]Cl was formed by reaction of LH3 with a rhenium(V) gluconate intermediate in water at pH 4.7. The 1∶1 complex [ReOL] was conjugated with the small protein N-TIMP-2 by aminolysis at a lysine residue, to form a 1∶1 adduct as established by electrospray mass spectrometry.

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Article type: Paper
DOI: 10.1039/A804717K
Citation: J. Chem. Soc., Dalton Trans., 1998,0, 3087-3092
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    Structural characterisation and bioconjugation of an active ester containing oxorhenium(V) complex incorporating a thioether donor

    M. Glaser, M. J. Howard, K. Howland, A. K. Powell, M. T. Rae, S. Wocadlo, R. A. Williamson and P. J. Blower, J. Chem. Soc., Dalton Trans., 1998, 0, 3087
    DOI: 10.1039/A804717K

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