Abstract
6,7 -Dideoxy-alpha-D-gluco-heptose 7-phosphonic acid, the isosteric phosphonate analogue of glucose 6-phosphate, was synthesized in six steps from the readily available precursor benzyl 4,6-O-benzylidene-alpha-D-glucopyranoside. The analogue is a substrate for yeast glucose 6-phosphate dehydrogenase, showing Michaelis-Menten kinetics at pH7.5 and 8.0. At both pH values the Km values of the analogue are 4-5 fold higher and the values approx. 50% lower than those of the natural substrate. The product of enzymic dehydrogenation of the phosphonate analogue at pH8.5 is itself a substrate for gluconate 6-phosphate dehydrogenase.
Full text
PDF
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Adams P. R., Harrison R. Dehydration of a phosphonate substrate analogue by glycerol 3-phosphate dehydrogenase. Biochem J. 1974 Sep;141(3):729–732. doi: 10.1042/bj1410729. [DOI] [PMC free article] [PubMed] [Google Scholar]
- 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]
- 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]
- 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]
- Jones G. H., Moffatt J. G. The synthesis of 6'-deoxyhomonucleoside-6'-phosphonic acids. J Am Chem Soc. 1968 Sep 11;90(19):5336–5338. doi: 10.1021/ja01021a086. [DOI] [PubMed] [Google Scholar]
- 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]
- 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]