Substrate stereochemistry of isovaleryl-CoA dehydrogenase. II. Steric course of C-3 hydrogen elimination

D. John Aberhart, Gaetano Finocchiaro, Yasuyuki Ikeda, Kay Tanaka

Research output: Contribution to journalArticle

Abstract

(3S)-[4-13C]Isovaleryl-CoA was prepared and dehydrogenated to 3-methylcrotonyl-CoA by pure rat liver isovaleryl-CoA dehydrogenase. In its 13C NMR spectrum, the product showed a single enriched 13C resonance at δ27.73. Signal assignment of the methyls of 3-methylcrotonyl-CoA (3-pro-Z, δ21.93; 3-pro-E, δ27.73) was made by synthesizing reference samples of 3-[4-13C]methylcrotonyl-CoA. In conjunction with our prior determination (D. J. Aberhart and C-H. Tann, 1981, Bioorg. Chem., 10, 200-205) that isovaleryl-CoA dehydrogenase removes the 2-pro-R hydrogen of isovaleryl-CoA, the results show that the dehydrogenation proceeds with anti elimination of hydrogens from C-2 and C-3 of the substrate.

Original languageEnglish
Pages (from-to)170-175
Number of pages6
JournalBioorganic Chemistry
Volume14
Issue number2
DOIs
Publication statusPublished - 1986

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery

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