Sulphinamoylacetates as sulphine precursors. Mechanism of basic hydrolysis and scheme of irreversible inactivation of cinnamoyl alcohol dehydrogenase, an enzyme of the lignification process

DOI: 10.1039/P29880001473

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 1473 - 1478 (1988)

Update date:2022-09-26

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Authors:

Baltes, Michel

Cazaux, Louis

Gorrichon, Liliane

Maroni, Pierre

Tisnes, Pierre

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Article abstract of DOI:10.1039/P29880001473

t-Butyl N-arylsulphinamoylacetates are hydrolysed in aqueous basic media by an elimination mechanism. It takes place on the conjugate base of the substrate resulting from a fast deprotonation of the activated methylene group. This elimination is first order (E1cB) for compounds where strong electron-withdrawing groups substitute the aromatic ring. For substitution by weaker electron-withdrawing or -donating groups, the elimination is second order, and needs the presence of general acid catalysis. For t-butyl N-(2-hydroxyphenyl)sulphinamoylisobutyrate where this mechanism of elimination is impossible, a B_Ac2 attack by hydroxide ion at the sulphur atom takes place. From these mechanisms and the results of complexation of zinc(II) cations by sulphinamoylacetates, a possible scheme for the irreversible inactivation of the title zinc metalloenzyme is proposed.

Full text of DOI:10.1039/P29880001473

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