Skip to main content
NCBI home page
Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1970 Dec;67(4):1669–1672. doi: 10.1073/pnas.67.4.1669

Mechanism and Stereochemistry of 5-Dehydroquinate Synthetase*

S L Rotenberg 1,†, D B Sprinson 1,‡
PMCID: PMC283410  PMID: 5275368

Abstract

3-Deoxy-D-arabino-heptulosonic acid 7-phosphate (DAHP) labeled at C-7 randomly or stereospecifically with tritium and at C-1 with 14C was converted enzymically to 5-dehydroquinate. Tritium of all three substrates was completely retained in 5-dehydroquinate, in accord with formation of a non-ketonizing 6,7-enol intermediate. The 5-dehydroquinates were dehydrated to 5-dehydroshikimate by 5-dehydroquinate dehydratase, which is known to catalyze a cis-elimination. Only 5-dehydroquinate derived from [7-3H](7R)-DAHP lost its tritium in this dehydration, indicating that the configuration at C-7 was inverted in the conversion of DAHP to 5-dehydroquinate.

Full text

PDF
1669

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. ADLERSBERG M., SPRINSON D. B. SYNTHESIS OF 3,7-DIDEOXY-D-THREO-HEPTO-2,6-DIULOSONIC ACID: A STUDY IN 5-DEHYDROQUINIC ACID FORMATION. Biochemistry. 1964 Dec;3:1855–1860. doi: 10.1021/bi00900a011. [DOI] [PubMed] [Google Scholar]
  2. BARTLETT G. R. Methods for the isolation of glycolytic intermediated by column chromatography with ion exchange resins. J Biol Chem. 1959 Mar;234(3):459–465. [PubMed] [Google Scholar]
  3. BAXTER J. N., PERLIN A. S., SIMPSON F. J. Preparation and assay of D-erythrose 4-phosphate. Can J Biochem Physiol. 1959 Feb;37(2):199–209. [PubMed] [Google Scholar]
  4. Barnett J. E., Corina D. L. The mechanism of glucose 6-phosphate-D-myo-inositol 1-phosphate cyclase of rat testis. The involvement of hydrogen atoms. Biochem J. 1968 Jun;108(1):125–129. doi: 10.1042/bj1080125. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. HANSON K. R., ROSE I. A. THE ABSOLUTE STEREOCHEMICAL COURSE OF CITRIC ACID BIOSYNTHESIS. Proc Natl Acad Sci U S A. 1963 Nov;50:981–988. doi: 10.1073/pnas.50.5.981. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. ROSE I. A., O'CONNELL E. L. Stereospecificity of the sugarphosphate isomerase reactions; a uniformity. Biochim Biophys Acta. 1960 Jul 29;42:159–160. doi: 10.1016/0006-3002(60)90765-4. [DOI] [PubMed] [Google Scholar]
  7. Rose I. A., O'Connell E. L., Noce P., Utter M. F., Wood H. G., Willard J. M., Cooper T. G., Benziman M. Stereochemistry of the enzymatic carboxylation of phosphoenolpyruvate. J Biol Chem. 1969 Nov 25;244(22):6130–6133. [PubMed] [Google Scholar]
  8. SPRINSON D. B., ROTHSCHILD J., SPRECHER M. THE SYNTHESIS OF 3-DEOXY-D-ARABINO-HEPTULOSONIC ACID 7-PHOSPHATE. J Biol Chem. 1963 Oct;238:3170–3175. [PubMed] [Google Scholar]
  9. SRINIVASAN P. R., ROTHSCHILD J., SPRINSON D. B. THE ENZYMIC CONVERSION OF 3-DEOXY-D-ARABINO-HEPTULOSONIC ACID 7-PHOSPHATE TO 5-DEHYDROQUINATE. J Biol Chem. 1963 Oct;238:3176–3182. [PubMed] [Google Scholar]

Articles from Proceedings of the National Academy of Sciences of the United States of America are provided here courtesy of National Academy of Sciences

RESOURCES