TY - JOUR
T1 - Dealkylation of Organotin Compounds by Biological Dithiols
T2 - Toward the Chemistry of Organotin Toxicity
AU - Buck, Bethany
AU - Mascioni, Alessandro
AU - Que, Lawrence
AU - Veglia, Gianluigi
PY - 2003/11/5
Y1 - 2003/11/5
N2 - In this Communication, we report evidence for the dealkylation of trialkyltin compounds by a short linear peptide extracted from a small membrane protein (stannin) involved in cellular apoptosis and containing a CXC motif. We show that (a) organotin binding induces the formation of a β-turn in the linear peptide, (b) both cysteines are necessary for the dealkylation reaction, and (c) stable 1:1 complexes are formed between the peptide and diorganotins that can be observed by ESI-MS. Organotin degradation by biological dithiols may be responsible for both the delayed activity of these toxins in humans and the organotin resistance mechanisms in bacteria.
AB - In this Communication, we report evidence for the dealkylation of trialkyltin compounds by a short linear peptide extracted from a small membrane protein (stannin) involved in cellular apoptosis and containing a CXC motif. We show that (a) organotin binding induces the formation of a β-turn in the linear peptide, (b) both cysteines are necessary for the dealkylation reaction, and (c) stable 1:1 complexes are formed between the peptide and diorganotins that can be observed by ESI-MS. Organotin degradation by biological dithiols may be responsible for both the delayed activity of these toxins in humans and the organotin resistance mechanisms in bacteria.
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U2 - 10.1021/ja0354723
DO - 10.1021/ja0354723
M3 - Article
C2 - 14583001
AN - SCOPUS:0242299272
SN - 0002-7863
VL - 125
SP - 13316
EP - 13317
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 44
ER -