Acyl phosphate salts and their use

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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435 89, 435 92, 435140, C07C15300

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047012854

ABSTRACT:
This invention consists of the production of a salt of acyl phosphate in an aqueous solution by a process which involves (1) acylation of phosphoric acid (H.sub.3 PO.sub.4) with an acid anhydride of the general formula RCOX, where R can be hydrogen or a lower alkyl or aryl group having from 1 to 10 carbon atoms, and X can be a leaving group of the general formula OR, OCOR, X or NR.sub.2, followed by (2a) extraction of acyl phosphate to water by treatment of the reaction mixture with an aqueous bicarbonate or hydroxide solution or other basic aqueous solution, if the reaction is carried out in non-aqueous solvent or (2b) in the case where water has been used as reaction solvent acidification with acid or acid form of a carbon exchange resin. After (3) extraction of residual carboxylic acid from the resulting acidic aqueous mixture using a solvent in which the acid is soluble but with which water does not mix, the remaining aqueous solution of acyl phosphate is (4) neutralized by addition of a base such as sodium or potassium hydroxide.

REFERENCES:
patent: 4088675 (1978-05-01), Whitesides et al.
Lynen, Feodor "Uber die gemischten Anhydride aus Phosphorsaure und Essigsaure" Chem. Ber. vol. 73 (1940) pp. 367-375.
Lipmann, F. and Tuttle, L. C. "Acetyl Phosphate: Chemistry, Determination, and Synthesis" J. Biol. Chem. vol. 153 (1944) pp. 571-582.
Bentley, Ronald "A New Synthesis of Acetyl Dihydrogen Phosphate" J. Amer. Chem. Soc. vol. 70 (1948) pp. 2183-2185.
Stadtman, E. R. & Lipmann, F. "Acetyl Phosphate Synthesis by Reaction of Isopropenyl Acetate and Phosphoric Acid" J.Biol. Chem. v.185 (1950) pp. 549-551.
Koshland, D. E., Jr. "Kinetics of Peptide Bond Formation" J. Amer. Chem. Soc. vol. 73 (1951) pp. 4103-4107.
Avison, A. W. D. "The Synthesis of Acyl Phosphates in Aqueous Solution" J. Chem. Soc. vol. 732 (1955) pp. 732-738.
Porter, R. W., et al. "Aspartate Transcarbamylase-Kinetic Studies of the Catalytic Subunit" J. Biol. Chem. vol. 244 (1969) pp. 1846-1859.
Heyde, E. et al. "Mechanism of the Reaction Catalyzed by the Catalytic Subunit of Aspartate Transcarbamylase. Kinetic Studies with Carbamyl Phosphate as Substrate" Biochemistry vol. 12, No. 23 (1973) pp. 4718-4726.
Whitesides, et al. "Large-Scale Synthesis of Diammonium Acetyl Phosphate" J. Org. Chem. vol. 40 (1975) pp. 2516-2519.

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