Skip to main content
PMC home page
Biochemical Journal logoLink to Biochemical Journal
. 1974 Sep;141(3):729–732. doi: 10.1042/bj1410729

Dehydrogenation of a phosphonate substrate analogue by glycerol 3-phosphate dehydrogenase

Paul R Adams 1, Roger Harrison 1, Thomas D Inch 2
PMCID: PMC1168179  PMID: 4463960

Abstract

S-(+)-3,4-Dihydroxybutylphosphonic acid, an isosteric analogue of sn-glycerol 3-phosphate, was synthesized stereospecifically and shown to be an effective substrate for rabbit muscle glycerol 3-phosphate dehydrogenase (sn-glycerol 3-phosphate–NAD+ oxidoreductase, EC 1.1.1.8). Non-isosteric phosphonate analogues of sn-glycerol 3-phosphate showed neither substrate nor inhibitory activity with the enzyme.

Full text

PDF
732

Selected References

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

  1. Baer E., Basu H. Phosphonic acid analogues of carbohydrate metabolites. I. Synthesis of L-and D-dihydroxypropylphosphonic acid. Can J Biochem. 1969 Oct;47(10):955–960. doi: 10.1139/o69-150. [DOI] [PubMed] [Google Scholar]
  2. Baer E., Nazir D. J., Basu H. Phosphonic acid analogues of carbohydrate metabolites. Dihydroxypropylphosphonic acid. II. Substrate specificity of L-glycerol-3-phosphate: NAD oxidoreductase. Can J Biochem. 1969 Oct;47(10):992–994. doi: 10.1139/o69-158. [DOI] [PubMed] [Google Scholar]
  3. Cheng P. J., Hickey R., Engel R., Tropp B. E. Rabbit muscle L-glycerol-3-phosphate dehydrogenase. Substrate activity of 3,4-dihydroxybutyl 1-phosphonate and 4-hydroxy-3-oxobutyl 1-phosphonate. Biochim Biophys Acta. 1974 Mar 21;341(1):85–92. doi: 10.1016/0005-2744(74)90068-0. [DOI] [PubMed] [Google Scholar]
  4. Dixon H. B., Sparkes M. J. Phosphonomethyl analogues of phosphate ester glycolytic intermediates. Biochem J. 1974 Sep;141(3):715–719. doi: 10.1042/bj1410715. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. FLORINI J. R., VESTLING C. S. Graphical determination of the dissociation constants for two-substrate enzyme systems. Biochim Biophys Acta. 1957 Sep;25(3):575–578. doi: 10.1016/0006-3002(57)90529-2. [DOI] [PubMed] [Google Scholar]
  6. Hampton A., Sasaki T., Paul B. Synthesis of 6'-cyano-6'-deoxyhomoadenosine-6'-phosphonic acid and its phosphoryl and pyrophosphoryl anhydrides and studies of their interactions with adenine nucleotide utilizing enzymes. J Am Chem Soc. 1973 Jun 27;95(13):4404–4414. doi: 10.1021/ja00794a043. [DOI] [PubMed] [Google Scholar]
  7. Kabak J., DeFilippe L., Engel R., Tropp B. Synthesis of the phosphonic acid isostere of glycerol 3-phosphate. J Med Chem. 1972 Oct;15(10):1074–1075. doi: 10.1021/jm00280a022. [DOI] [PubMed] [Google Scholar]
  8. Orr G. A., Knowles J. R. The interaction of the phosphonate analogue of 3-phospho-D-glycerate with phosphoglycerate kinase. Biochem J. 1974 Sep;141(3):721–723. doi: 10.1042/bj1410721. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Paulsen H., Bartsch W., Thiem J. Phosphorhaltige Kohlenhydrate. 3. Darstellung von Zuckerphosphonaten durch Wittig- udn Horner-Reaktion. Chem Ber. 1971;104(8):2545–2552. doi: 10.1002/cber.19711040823. [DOI] [PubMed] [Google Scholar]
  10. Rosenthal A. F., Pousada M. Inhibition of phospholipase C by phosphonate analogs of glycerophosphatides. Biochim Biophys Acta. 1968 Oct 22;164(2):226–237. doi: 10.1016/0005-2760(68)90149-5. [DOI] [PubMed] [Google Scholar]
  11. Stribling D. Properties of the phosphonomethyl isosteres of two phosphate ester glycolytic intermediates. Biochem J. 1974 Sep;141(3):725–728. doi: 10.1042/bj1410725. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Biochemical Journal are provided here courtesy of The Biochemical Society

RESOURCES