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

Glaser, M. and Howard, M.J. and Howland, K. and Powell, A.K. and Rae, M.T. and Wocadlo, S. and Williamson, R.A. and Blower, P.J. (1998) Structural characterisation and bioconjugation of an active ester containing oxorhenium(V) complex incorporating a thioether donor. Journal of the Chemical Society-Dalton Transactions (18). pp. 3087-3092. ISSN 0300-9246. (The full text of this publication is not available from this repository)

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Official URL
http://dx.doi.org/10.1039/a804717k

Abstract

A simple new 2,3,5,6-tetrafluorophenyl ester containing diamide-thioether-thiol bifunctional chelating agent LH3, HS(CH2)(2)SCH2C(O)NHCH2C(O)NH(CH2)(3)C(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.

Item Type: Article
Subjects: Q Science > QD Chemistry
Divisions: Faculties > Science Technology and Medical Studies > School of Biosciences
Depositing User: R.F. Xu
Date Deposited: 30 Jun 2009 12:14
Last Modified: 30 Jun 2009 12:14
Resource URI: http://kar.kent.ac.uk/id/eprint/17770 (The current URI for this page, for reference purposes)
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