NDLI: Stereochemistry of the 3-deoxy-D-arabino-heptulosonate 7-phosphate synthetase reaction and the chorismate synthetase reaction.

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Stereochemistry of the 3-deoxy-D-arabino-heptulosonate 7-phosphate synthetase reaction and the chorismate synthetase reaction.

Content Provider	Semantic Scholar
Author	Floss, Heinz G. Onderka, Detlef K. Carroll, Mark
Copyright Year	1972
Abstract	Abstract (Z)- and (E)-[3-3H]P-enolpyruvate were prepared from [1-3H]glucose and [1-3H]mannose with the glycolytic enzymes and were converted into shikimates tritiated at C-6 with non-labeled erythrose-4-P and cell-free extract of Escherichia coli mutant 83-24. Degradation to malate and analysis by the fumarase reaction showed that (Z)-[3-3H]P-enolpyruvate had produced [6-3H]shikimate of predominantly 6R configuration and the E isomer had given predominantly (6S)-[6-3H]shikimate. The DAHP synthetase reaction therefore is stereospecific with respect of C-3 of P-enolpyruvate, involving si attack at this center. As a consequence, the transient formation of a methyl group at C-3 of P-enolpyruvate as part of the reaction, as proposed by DeLeo and Sprinson ((1968) Biochem. Biophys. Res. Commun., 32, 873), is unlikely. Further conversion of (6R)- and (6S)-[6-3H]shikimate into chorismate showed that the pro-6R hydrogen is eliminated in this process. Thus, the 1,4-conjugate elimination of phosphoric acid in the chorismate synthetase reaction is anti, rendering a concerted (E2') mechanism unlikely.
File Format	PDF HTM / HTML
PubMed reference number	4550759
Journal	Medline
Volume Number	247
Issue Number	3
Alternate Webpage(s)	http://www.jbc.org/content/247/3/736.full.pdf
Journal	The Journal of biological chemistry
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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