DE1518361B1 - L-ornithine-L-asparaginate and process for its preparation - Google Patents

Claims (4)

1 2 The invention relates to L-ornithine-L-asparaginate and is of considerable importance. L-aspartic acid is also included a process for its manufacture. as starting material in the biosynthesis of Orot- It is known that L-ornithine is an acid important for growth. is not a necessary amino acid in rats, but the process of the invention for the preparation of in the metabolism of the living body as a member of the 5 L-ornithine-L-asparaginate consists in that one The omithin cycle in the production of urea contains an L-ornithine and L-aspartic acid in solution. plays an essential role. implemented differently. It is also known that aspartic acid has the properties of. The compound in the anhydrous state has the Runner of oxaloacetate or fumarate of citric acid - the following formula:
cycle and as an amino supplier in the omithin cycle from io [NH ₃ - (CHa) ₃ -CH-COOHj NH _B 0OC - CH ₂ - CH - COOH [NH ₂ It is already known that when administered intravenously, Example 1
enrichment of L-ornithine or L-aspartic acid Animals with a high ammonia content in the blood received 20 16.8 g of L-ornithine hydrochloride in 400 ml Significant decrease in ammoniacal nitrogen dissolved. The solution was through a layer Substance and an increase in blood urea occurs. of 150 ml of the cation exchange resin »Amber- It has been assumed that these phenomena passed through lite IR-120 «in the ammonium form, partly due to the acceleration of the hepatic The resin was then washed with 100 ml of water The omithin cycle can be traced back to an extra acceleration of 5% and 11 5% aqueous ammonia solution Degradation of blood ammonia leads. here. According to the method according to the invention, the effluate was removed by evaporation of ammo The L-ornithine-L-asparaginate is now surprisingly released. The resulting L-ornithine solution was thus considerably more effective in treating with 11.8 g of L-aspartic acid mixed and with 30 ml Hyperammonemia. 30 diluted with water. As already stated, according to the invention the salt can be heated to dissolve the asparagine of L-ornithine and L-aspartic acid by acid, and then in vacuo to a total exposure of L-ornithine with L-aspartic acid of 28 g constricted. The mixture was made with to be made. The reaction of the ornithine and the 4 ml of methanol were added and the mixture was left to stand overnight. Aspartic acid can simply be brought about by 35 The precipitated crystals were filtered off by washing the two substances in the solution with one another, methanol and drying. One obtained to be mixed. The solvent used is water. 24 g of L-ornithine-L-asparaginate monohydrate, which is preferred. Aqueous solution of decomposition of 215 ° C melted:
Solutions of L-ornithine and L-aspartic acid, gives analysis for C ₉ H ₁₉ O ₆ N ₃ · H ₂ O
methanol is added to the mixture and allowed to crystallize out. If necessary, the mixture can be concentrated, B «ctarf ... C 38.00, H 7.13, N 14.47, H ₂ O 6 70; until crystallization occurs. The salt of L-ornithine p ^e ^ ^nden , I " 2 ' i ™, ¹ S?' ^Ν _Λ ¹⁴ ' ⁸³ ' ^H2 ° ^{6 '37} and L-aspartic acid crystallizes out. The so- M »= + ⁷ ^ ( ^conc . 38% water). The salt retained crystallizes from aqueous methanol. -19 usually with 1 mole of water, i.e. H. as a monohydrate. 45 B e 1 s ρ 1 e 1 2 The water of hydration can by prolonged heating in 30 ml of an aqueous solution containing 40 g of free DL-Or- contained entnithine in a dry atmosphere or in a vacuum, were mixed with 14 g of L-aspartic acid removed, but resumed when mixed. The mixture was heated to the the compound is exposed to humid air. Dissolve aspartic acid, cooled to 25 ° C, with The hydrate melts with decomposition at 215 to 5 ° 20 ml of methanol are mixed and at the same temperature 217 ° C. Its specific rotation [<x] ² S is left to stand at temperature overnight. The educated 38% concentration in water + 7.1. After a crystal was filtered off, with 20 ml of a 50% Another embodiment of the aqueous methanol solution according to the invention washed and dried. In the process, L-ornithine-L-asparaginate can produce 12.6 g of D-ornithine-L-asparaginate, which undergoes decomposition are melted by reacting L-aspartic acid with 55 at 215 ° C was obtained. The specific a mixture of D-ornithine and L-ornithine, and rotation of the product in 38% strength aqueous solution, ^it fractional crystallization of the product from aq at 20 ° C was -7 °. red methanol. In this case, the mother liquor from which the D-ornithine-L-aspara- L-aspartic acid salt from D-ornithine first, and ginat had been filtered off, was mixed with 100 ml of L-ornithine-L-asparaginate remains in the mother liquor. 60 ethanol mixed and stirred. The resulting low From this it can be filtered off by adding methanol or blown, washed with methanol be separated by evaporation. When you get one and dried. 11 g L-ornithine-L-asparaginate mono- If you want to produce a product of greater purity, you can hydrate it with decomposition at 214 to 215 ° C this by recrystallizing the first product from melted was obtained. achieve aqueous methanol. A mix of 65 .., Ethanol and water can also be used for crystallization. if used. The invention is in the following 1. L-ornithine-L-asparaginate. the examples below. 2. Process for the production of L-ornithine 3 4 L-asparaginate, characterized in that it is characterized in that DL-ornithine with L-As- L-ornithine and L-aspartic acid in solution with-paragic acid are converted and fractionated implements each other. Crystallization of the optically active L-ornithine 3. The method according to claim 2, characterized by separating L-asparaginate. draws that the reaction in aqueous Lö- 5 5. The method according to any one of claims 2 to 4, solution. characterized in that the crystallization 4. The method according to claim 2 or 3, characterized in that it is carried out from aqueous methanol or ethanol.