Stereochemistry of Krebs' cycle hydrations and related reactions

Oscar Gawron, Andrew J. Glaid, Thomas P Fondy

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

3-Deuterio-L-malic acid obtained from the fumarase catalyzed hydration of fumaric acid in D 2O is shown to have the erythro configuration by n.m.r. comparison with stereospecifically synthesized threo-3-deuterio-DL-malic acid. The fumarase and aspartase systems thus operate by a trans mechanism as do the β-methylaspartase and cis-aconitase systems. Brewster's rules are applied to the problem of the stereochemistry of citric acid synthesized in the Krebs cycle and a configuration related to D-malic acid is arrived at. This configuration plus the α DsLs configuration of d-isocitric acid permits depiction of the stereochemical pathway of the cis-aconitase system and of the reactions of the Krebs cycle. The possibility that cis-aconitase exhibits a preferred direction for addition of OH, with concomitant trans addition of H, is discussed.

Original languageEnglish (US)
Pages (from-to)3634-3640
Number of pages7
JournalJournal of the American Chemical Society
Volume83
Issue number17
StatePublished - 1961
Externally publishedYes

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Aconitate Hydratase
Stereochemistry
Citric Acid Cycle
Fumarate Hydratase
Hydration
Acids
Aspartate Ammonia-Lyase
Citric Acid
Citric acid
malic acid

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Stereochemistry of Krebs' cycle hydrations and related reactions. / Gawron, Oscar; Glaid, Andrew J.; Fondy, Thomas P.

In: Journal of the American Chemical Society, Vol. 83, No. 17, 1961, p. 3634-3640.

Research output: Contribution to journalArticle

Gawron, Oscar ; Glaid, Andrew J. ; Fondy, Thomas P. / Stereochemistry of Krebs' cycle hydrations and related reactions. In: Journal of the American Chemical Society. 1961 ; Vol. 83, No. 17. pp. 3634-3640.
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