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

Glaser, Matthias, Howard, Mark J., Howland, Kevin, Powell, Anne K., Rae, Michael T., Wocadlo, Sigrid, Williamson, Richard A., Blower, Philip 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. (doi:10.1039/a804717k) (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided) (KAR id:17770)

The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided.
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
DOI/Identification number:	10.1039/a804717k
Subjects:	Q Science > QD Chemistry
Divisions:	Divisions > Division of Natural Sciences > Biosciences
Depositing User:	R.F. Xu
Date Deposited:	30 Jun 2009 12:14 UTC
Last Modified:	16 Nov 2021 09:55 UTC
Resource URI:	https://kar.kent.ac.uk/id/eprint/17770 (The current URI for this page, for reference purposes)

University of Kent Author Information

Howard, Mark J..

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Howland, Kevin.

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Williamson, Richard A..

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Blower, Philip J..

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