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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Thioacylating agents as ultimate intermediates in the beta-lyase catalysed metabolism of S-(pentachloro-butadienyl)-L-cysteine.

The transformation of the hexachloro-1,3-butadiene metabolite S-(1,2,3,4,4-pentachlorobuta-1,3-dienyl)-L-cysteine (PCBC) by bacterial cysteine conjugate beta-lyase (beta-lyase) and by N-dodecylpyridoxal bromide (PLP-Br) was investigated using GC/MS to identify products formed. PCBC was transformed by both bacterial beta-lyase and PLP-Br to the major products 2,3,4,4-tetrachlorobutenoic acid and 2,3,4,4-tetrachlorothiobutenoic acid, and to the minor metabolites trichloroacetic acid and S-(1,2,3,4,4-pentachlorobuta-1,3-dienyl)-mercaptoacetic acid. In the presence of diethylamine as model nucleophile, PLP-Br transformed PCBC to yield 2,3,4,4-tetrachlorothiobutenoic acid diethylamide; attempts to trap 1,2,3,4,4-pentachlorobutadienyl thiol, the initial metabolite formed by beta-elimination from PCBC, were unsuccessful. The results obtained suggest that the formation of a thioacylating intermediate (a thioketene or a thiono acyl chloride) may be the decisive reaction during the beta-lyase dependent activation of PCBC.[1]


  1. Thioacylating agents as ultimate intermediates in the beta-lyase catalysed metabolism of S-(pentachloro-butadienyl)-L-cysteine. Dekant, W., Berthold, K., Vamvakas, S., Henschler, D. Chem. Biol. Interact. (1988) [Pubmed]
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