Abstract
THE recent synthesis and stereochemical analysis of a phosphate monoester chiral at phosphorus by virtue only of the three stable isotopes of oxygen1,2 opens the way to the determination of the stereochemical course of both chemical and enzymatic reactions that involve the transfer of a phosphoryl group. We report here the first determination of the stereochemical consequence at phosphorus of an intermolecular phosphoryl transfer reaction. In studying the reaction catalysed by alkaline phosphatase we had two aims: first, to discover the stereochemical course of this well-studied transfer, and second to devise a general method by which the configuration of any chiral phosphate monoester can be determined.
Your institute does not have access to this article
Access options
Subscribe to Journal
Get full journal access for 1 year
$199.00
only $3.90 per issue
All prices are NET prices.
VAT will be added later in the checkout.
Tax calculation will be finalised during checkout.
Buy article
Get time limited or full article access on ReadCube.
$32.00
All prices are NET prices.
References
Abbott, S. J., Jones, S. R., Weinman, S. A. & Knowles, J. R. J. Am. chem. Soc. 100, 2558–2560 (1978).
Cullis, P. M. & Lowe, G. J. chem. Soc. chem. Commun. 512–514 (1978).
Reid, T. W. & Wilson, I. B. The Enzymes, 3rd edn IV, 373–415 (1971).
Wilson, I. B., Dayan, J. & Cyr, K. J. biol. Chem. 239, 4182–4185 (1964).
Koshland, D. E. Symposium on the Mechanism of Enzyme Action (eds McElroy, D. E. & Glass, B.) 608–641 (Johns Hopkins Press, Baltimore, 1954).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
JONES, S., KINDMAN, L. & KNOWLES, J. Stereochemistry of phosphoryl group transfer using a chiral [16O, 17O, 18O] stereochemical course of alkaline phosphatase. Nature 275, 564–565 (1978). https://doi.org/10.1038/275564a0
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/275564a0
Further reading
-
The pH-dependent activation mechanism of Ser102 in Escherichia coli alkaline phosphatase: a theoretical study
JBIC Journal of Biological Inorganic Chemistry (2018)
-
Cellular function and molecular structure of ecto-nucleotidases
Purinergic Signalling (2012)
-
Unfolding and Inactivation of Abalone (Haliotis diversicolor) Alkaline Phosphatase During Denaturation by Guanidine Hydrochloride
Applied Biochemistry and Biotechnology (2009)
-
Kinetics of inhibition of alkaline phosphatase from green crab (Scylla serrata) by N-bromosuccinimide
Journal of Protein Chemistry (1996)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.