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United States Patent Office Patented Jan 2,700,038 United States Patent Office Patented Jan. 18, 1955 2 tating with alcohol, the salts which separate would cor respond to the pH-composition titration curves. To our 2,700,038 Suprise, this has not been found to be the case, the di basic salts being precipitated from strongly acidified solu DIBASIC SALTS OF ADENOSINE TRIPHOSPHATE tions. This may be illustrated as follows: On adding AND METHOD OF PREPARATION either sodium, potassium or lithium chloride to an acidi Samuel H. Lipton, Milwaukee, and Samuel A. Morell, fied aqueous solution of the free adenosine triphosphoric Whitefish Bay, Wis., assignors to Pabst Brewing Com acid which is free of cations other than hydrogen ion, and pany, Milwaukee, Wis., a corporation of Delaware then adding an alcohol such as ethanol, methanol or pro O panol, the diabasic salts separate and are found to be No Drawing. Application September 27, 1951, free of chloride ion. For example, a 5% solution of Serial No. 248,632 adenosine triphosphoric acid was adjusted to pH 1.0 by adding hydrochloric acids, then sodium chloride was add 13 Claims. (C. 260-211.5) ed to 1% concentration and the solution was poured into 4 volumes of ethanol. After filtering, washing with adenosineThis invention triphosphoric relates acid, to amore new particularlyand useful asalt water of ethanol and drying, the product was found to be disodium soluble dibasic salt, and to a method for the preparation dihydrogen adenosine triphosphate of high purity and thereof. free of chloride ion. As is well known in the art (P. Ostern, U. S. Patent In our process for preparing a dibasic salt of adenosine 2,174,475; G. Henning, German Patents 703,400, 20 triphosphoric acid from yeast fermentation mixtures, we 708,624) the addition of adenosine and inorganic phos prefer to isolate the product in two stages, a less pure and phate to a yeast fermentation system results in the a highly purified form. In both stages of this process, ad enzymatic synthesis of adenosine-5'-phosphate (AMP, or vantage is taken of our discovery that a dibasic adenosine muscle adenylic acid) and the corresponding polyphos triphosphate may be precipitated from strong acid solu phates, viz., the diphosphate and the triphosphate. The 25 tions as described above. The fermentation medium in polyphosphates are very labile compounds, particularly which adenosine triphosphoric acid is formed from in alkaline solution, and tend to become hydrolyzed, dur adenosine contains large amounts of inorganic phosphate. ing their isolation, to the more stable AMP. One great advantage of our isolation process is the fact Methods heretofore employed for obtaining adenosine that dibasic adenosine triphosphate obtained directly from triphosphoric acid, either from a filtered fermentation 30 the complex fermentation mixture is substantially free of mixture or from a muscle or other tissue extract, have in inorganic phosphate and is 80% to 90% pure. volved the following essential steps: (1) precipitation Although the dibasic adenosine triphosphate obtained of a water insoluble salt of adenosine triphosphoric acid, directly from the fermentation mixture is sufficiently pure such as that of barium, mercury, lead, silver and copper, for various chemical, biochemical and other purposes, usually from alkaline solutions where such salts exhibit 35 it contains certain impurities, such as calcium, mag lowered solubility; (2) double decomposition of these nesium, etc., which are inhibitory to some delicate salts with acids to form inorganic salts which are in enzymatic systems in which it may be employed. These soluble in the acids employed for the decomposition, such impurities are easily removed by well known ion ex as barium sulfate, lead sulfide, mercuric sulfide and silver change procedures. Thus, the dibasic adenosine tri chloride, thus liberating the free adenosine triphosphoric 40 phosphate is dissolved in water, passed through an ion ex acid in solution; and (3) either directly precipitating the change resin and again precipitated from a strong acid free acid with water miscible organic solvents, or first solution by adding a salt (e.g., NaCl, KCl or LiCl) and neutralizing to a salt, such as tetrasodium or tetrapo a water miscible organic solvent. The purity of the di tassium adenosine triphosphate, and then precipitating basic salt so obtained is 85% to 100%, depending upon with a water miscible organic solvent. 45 the particular ion-exchange process employed. The di One of the objects of the present invention is to pre basic adenosine triphosphates are stable when stored at pare a new and useful salt of adenosine triphosphoric 0 C., readily soluble in water, and after pH adjustment acid which is stable, readily soluble in water and can be to any desired range, can be used directly in various used directly in chemical enzymatic, clinical and other chemical, enzymatic, clinical, or other applications. applications. 50 As an illustrative embodiment of the manner in which Another object of the invention is to prepare a com the invention may be practiced, the following examples pound of the type described by a process which is simpler, are presented: more direct and less expensive than processes heretofore Example I employed to prepare adenosine triphosphoric acid and its 55 Ten (10) grams of adenosine are dissolved in a liter neutral salts. Other objects will appear hereinafter. of 0.1 molar sodium orthophosphate buffer of pH 7. After In accordance with this invention, we have discovered the addition of 250 grams of fresh brewer's yeast and 5 that in the presence of a sufficient concentration of alkali ml. of toluene, the mixture is stirred for 2 hours at 25 metal ions in an aqueous solution containing adenosine C. Small samples are then removed every 15 minutes triphosphoric acid, even in a strongly acidified solution, 60 for inorganic phosphate analysis. As soon as maximum a dibasic salt of said acid is precipitated by a water uptake of inorganic phosphate has occurred, which usual miscible organic solvent. It is hence unnecessary, in ly requires 2 to 5 hours, the reaction is interrupted by fact detrimental to both purity and yield, to conduct the cooling to 0° C. and adding 50 ml. of 70% perchloric laborious steps of heavy metal precipitation, decomposi acid. After filtering, and washing the filter cake with tion, and reprecipitation heretofore employed in the art. 65 water, the solution is poured into 4 volumes of 95% As may be seen from its formula ethanol. The precipitate is filtered, washed with ethanol and dried. It is disodium dihydrogen adenosine tri phosphate, Na2H2ATP.4H2O, of 80% to 90% purity. 70 Example II S. C C H O O O Ten (10) grams of disodium dihydrogen adenosine triphosphate, prepared as described in Example I, are n Y-8-6-6-6-6-0--0-1-0-1l-oh dissolved in 200 ml. of water, passed through a 1 inch # h H. H. H. H. (bH &H 75 by 20 inch bed of cation exchange resin which is in the adenosine triphosphoric acid is a strong acid which hydrogen form, and the column then washed with 100 contains four titratable hydrogen ions. In the dibasic salt, ml. of water. To the effluent, which is now free of all two of these ions are replaced by alkali metal ions. From inorganic cations except hydrogen ion, is added 4 grams elecrometric titration data, it might be expected that on of sodium chloride and 10 ml. of constant boiling hy adjusting an adenosine triphosphoric acid solution to 80 drochloric acid. After adding 4 volumes of 95% various pH levels with an alkali hydroxide, and precipi ethanol, filtering, washing and drying, 9 grams of disodium 2,700,088 3 4 hydrogen adenosine triphosphate, Na2H2ATP.4H2O, are pH is preferably hydrochloric, chloric, perchloric, tri obtained, of which the following is a typical analysis: chloroacetic, sulfuric or nitric. In making the dibasic salts of adenosine triphosphoric acid by yeast fermentation procedures the preferred steps Observed Theory 5 in the practice of the present invention are (a) buffering the reaction mixture of adenosine and yeast in the pH Adenine by E-260, micromols permg---------- 1.54 160 range of 6 to 7 with primary and secondary phosphates Molar Ratio, Adenine:Labile P:Organic P---- 1:2.00:3.02 1:2:3 Inorganic Phosphate, micronols per mg------- 0.04 0 of monovalent alkali metals, (b) cooling to 0° C. to Neutralization Equivalent, micromols alkali 5 C. after the formation of adenosine triphosphate has Pef Ing-------------------------------------- 3.27 3.2. 10 reached substantially a maximum level, (c) adding a Percent ATP by Electrophoretic Assay----- 89.3 100.0 strong acid (e.g., any of the acids previously mentioned) Percent ATP by Resin Assay (J. Ann. Chem. in an amount sufficient to effect dealbuminization, pref Soc., 72, 4278 (1950)).------------------------ 86.5 100.0 erably to a pH of 1 or less, (d) filtering, (e) adding a water miscible organic solvent to the filtrate to precipi Example III 5 tate the dibasic salt of adenosine triphosphoric acid of 80% to 90% purity. Ten (10) grams of disodium dihydrogen adenosine tri if a very pure product is desired, the purification is phosphate are passed through a cation exchange column preferably effected by passing solutions of the dibasic exactly as described in Example II. Instead of adding adenosine phosphate through ion exchange bodies (either 4 grams of sodium chloride to the effluent, however, 4 20 cationic or anionic or both) capable of removing all in grams of potassium chloride are added. The product is organic ions except hydrogen, and then adding a salt dipotassium dihydrogen adenosine triphosphate. of an alkali metal, a strong acid and a water miscible Example IV organic solvent. The concentrations of the salt which is added to the Ten (10) grams of disodium dihydrogen adenosine tri 25 adenosine triphosphoric acid, or is present in a reaction phosphate, prepared as described in Example I, are dis mixture containing said acid, are subject to variation.
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