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Issue 8, 1988
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Mechanistic studies on lysine 2,3-aminomutase: carbon-13—deuterium crossover experiments

D. John Aberhart  and  Jacques-Alain Cotting 

Abstract

A mixture of L-[3,3-2H2]lysine plus L-[2-13C]lysine is converted by purified lysine 2,3-aminomutase into β-lysine. The di-N-phthaloyl methyl ester derivative of the resultant β-lysine shows a geminally deuterium-coupled enriched 13C n.m.r. signal indicating intermolecular transfer of the migrating 3-pro-R hydrogen of the α-lysine. L-[3-13C]Lysine has been synthesized. A mixture of L-[3,3-2H2]lysine plus L-[3-13C]lysine is similarly converted into β-lysine. Its di-N-phthaloyl methyl ester derivative shows a β-shifted enriched 13C n.m.r. signal for C-3, but no geminally coupled enriched C-3 signal. The latter experiment rules out any intermolecular exchange of the non-migrating 3-pro-S hydrogen atom of α-lysine. Various mechanistic possibilities for the intermolecular hydrogen transfer process are discussed.

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Article type: Paper
DOI: 10.1039/P19880002119
Citation: J. Chem. Soc., Perkin Trans. 1, 1988,0, 2119-2122
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    Mechanistic studies on lysine 2,3-aminomutase: carbon-13—deuterium crossover experiments

    D. J. Aberhart and J. Cotting, J. Chem. Soc., Perkin Trans. 1, 1988, 0, 2119
    DOI: 10.1039/P19880002119

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