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Pseudoenzymatic dealkylation of alkyltins by biological dithiols

TitlePseudoenzymatic dealkylation of alkyltins by biological dithiols
Publication TypeArticolo su Rivista peer-reviewed
Year of Publication2009
AuthorsPorcelli, F., Triggiani Doriana, Buck-Koehntop B.A., Masterson L.R., and Veglia G.
JournalJournal of Biological Inorganic Chemistry
Volume14
Pagination1219-1225
ISSN09498257
Keywordsalkylating agent, Alkylation, alpha chemokine, amino acid derivative, Amino Acid Sequence, Animals, arginine, article, chemical reaction kinetics, covalent bond, Cysteine, dealkylation, dithiol derivative, Electrospray Ionization, enzymatic degradation, enzyme activity, fluorescence, Glycine, Humans, leucine, Mass, membrane protein, Molecular Structure, Neuropeptides, Organotin Compounds, Peptides, priority journal, species differentiation, Spectrometry, stannin, Tin, Toluene, tryptophan, tyrosine, unclassified drug
Abstract

We investigated the time dependence of the degradation of three alkyltin derivatives by a nine amino acid linear peptide (I1LGCWCYLR 9) 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. © 2009 SBIC.

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URLhttps://www.scopus.com/inward/record.uri?eid=2-s2.0-70449531506&doi=10.1007%2fs00775-009-0565-x&partnerID=40&md5=625306b62cb7481a42d006d5d047d476
DOI10.1007/s00775-009-0565-x
Citation KeyPorcelli20091219