New substrates, new inhibitors and the stereochemistry of the succinic dehydrogenase system

Oscar Gawron, Andrew J. Glaid, Thomas P Fondy, Mary M. Bechtold

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

L-Chlorosuccinate and L-methylsuccinate are substrates for succinic dehydrogenase, chlorofumarate and mesaconate being produced, respectively, by enzyme catalyzed dehydrogenation. The respective enantiomorphs, D-chlorosuccinate and L-methylsuccinate, are inhibitors of the enzyme and the stereospecificity of succinic dehydrogenase is thereby established. The enzyme exhibits a trans stereoselectivity, dehydrogenating erythro-3-deuterio-L-chlorosuccinate to 3-deuterio-chlorofumarate. From the above facts the stereochemistry of the behavior of succinic acid in the enzyme substrate complex is deduced. K M values and K I values for the new substrates under specified conditions are presented and E 0′ values at pH 7.3, 34° for the chlorosuccinate/chlorofumarate and methylsuccinate/mesaconate half-cells are 0.0462 volt and -0.0018 volt, respectively.

Original languageEnglish (US)
Pages (from-to)3877-3882
Number of pages6
JournalJournal of the American Chemical Society
Volume84
Issue number20
StatePublished - 1952
Externally publishedYes

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Stereochemistry
Succinate Dehydrogenase
Enzymes
Substrates
Stereoselectivity
Succinic Acid
Enzyme Inhibitors
Dehydrogenation
Acids
Oxidoreductases

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

New substrates, new inhibitors and the stereochemistry of the succinic dehydrogenase system. / Gawron, Oscar; Glaid, Andrew J.; Fondy, Thomas P; Bechtold, Mary M.

In: Journal of the American Chemical Society, Vol. 84, No. 20, 1952, p. 3877-3882.

Research output: Contribution to journalArticle

Gawron, Oscar ; Glaid, Andrew J. ; Fondy, Thomas P ; Bechtold, Mary M. / New substrates, new inhibitors and the stereochemistry of the succinic dehydrogenase system. In: Journal of the American Chemical Society. 1952 ; Vol. 84, No. 20. pp. 3877-3882.
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N2 - L-Chlorosuccinate and L-methylsuccinate are substrates for succinic dehydrogenase, chlorofumarate and mesaconate being produced, respectively, by enzyme catalyzed dehydrogenation. The respective enantiomorphs, D-chlorosuccinate and L-methylsuccinate, are inhibitors of the enzyme and the stereospecificity of succinic dehydrogenase is thereby established. The enzyme exhibits a trans stereoselectivity, dehydrogenating erythro-3-deuterio-L-chlorosuccinate to 3-deuterio-chlorofumarate. From the above facts the stereochemistry of the behavior of succinic acid in the enzyme substrate complex is deduced. K M values and K I values for the new substrates under specified conditions are presented and E 0′ values at pH 7.3, 34° for the chlorosuccinate/chlorofumarate and methylsuccinate/mesaconate half-cells are 0.0462 volt and -0.0018 volt, respectively.

AB - L-Chlorosuccinate and L-methylsuccinate are substrates for succinic dehydrogenase, chlorofumarate and mesaconate being produced, respectively, by enzyme catalyzed dehydrogenation. The respective enantiomorphs, D-chlorosuccinate and L-methylsuccinate, are inhibitors of the enzyme and the stereospecificity of succinic dehydrogenase is thereby established. The enzyme exhibits a trans stereoselectivity, dehydrogenating erythro-3-deuterio-L-chlorosuccinate to 3-deuterio-chlorofumarate. From the above facts the stereochemistry of the behavior of succinic acid in the enzyme substrate complex is deduced. K M values and K I values for the new substrates under specified conditions are presented and E 0′ values at pH 7.3, 34° for the chlorosuccinate/chlorofumarate and methylsuccinate/mesaconate half-cells are 0.0462 volt and -0.0018 volt, respectively.

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