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Pseudoenzymatic dealkylation of alkyltins by biological dithiols

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Abstract

We investigated the time dependence of the degradation of three alkyltin derivatives by a nine amino acid linear peptide (I1LGCWCYLR9) containing a CXC motif derived from the primary sequence of stannin, a membrane protein involved in alkyltin toxicity. We monitored the reaction kinetics using the intrinsic fluorescence of the tryptophan residue in position 5 of the peptide and found that all of the alkyltins analyzed are progressively degraded to dialkyl derivatives, following a pseudoenzymatic reaction mechanism. The end point of the reactions is the formation of a covalent complex between the disubstituted alkyltin and the peptide cysteines. These data agree with the speciation profiles proposed for polysubstituted alkyltins in the environment and reveal a possible biotic degradation pathway for these toxic compounds.

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Fig. 1
Fig. 2
Scheme 1

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Abbreviations

ESI-MS:

Electrospray ionization mass spectrometry

SNN:

Stannin

TET:

Triethyltin chloride

TetraMT:

Tetramethyltin

TMT:

Trimethyltin chloride

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Acknowledgments

Acknowledgment is made to the donors to the Petroleum Research Fund, administrated by the American Chemical Society, for partial support of this research. B.B. was supported by NIH Chemical Biology Interface Training Grant GM-08700.

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Authors and Affiliations

  1. Department of Environmental Science, University of Tuscia, 01100, Viterbo, Italy

    Fernando Porcelli & Doriana Triggiani

  2. Department of Molecular Biology and Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA

    Bethany A. Buck-Koehntop

  3. Department of Chemistry, University of Minnesota, Minneapolis, MN, 55455, USA

    Bethany A. Buck-Koehntop, Larry R. Masterson & Gianluigi Veglia

  4. Department of Biochemistry, Biophysics, and Molecular Biology, University of Minnesota, Minneapolis, MN, 55455, USA

    Larry R. Masterson & Gianluigi Veglia

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  1. Fernando Porcelli
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  2. Doriana Triggiani
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  3. Bethany A. Buck-Koehntop
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  4. Larry R. Masterson
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  5. Gianluigi Veglia
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Correspondence to Gianluigi Veglia.

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Porcelli, F., Triggiani, D., Buck-Koehntop, B.A. et al. Pseudoenzymatic dealkylation of alkyltins by biological dithiols. J Biol Inorg Chem 14, 1219–1225 (2009). https://doi.org/10.1007/s00775-009-0565-x

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