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WO1999027799A1 - Procede pour la production et l'utilisation de formiate de lysine - Google Patents

Procede pour la production et l'utilisation de formiate de lysine Download PDF

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Publication number
WO1999027799A1
WO1999027799A1 PCT/EP1998/007437 EP9807437W WO9927799A1 WO 1999027799 A1 WO1999027799 A1 WO 1999027799A1 EP 9807437 W EP9807437 W EP 9807437W WO 9927799 A1 WO9927799 A1 WO 9927799A1
Authority
WO
WIPO (PCT)
Prior art keywords
lysine
feed
formates
formic acid
lysm
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1998/007437
Other languages
German (de)
English (en)
Inventor
Ulrich Eidelsburger
Linda VON DEM BUSSCHE-HÜNNEFELD
Joachim Meyer
Günter Gaus
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to AU17558/99A priority Critical patent/AU1755899A/en
Publication of WO1999027799A1 publication Critical patent/WO1999027799A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/142—Amino acids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K30/00—Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs
    • A23K30/10—Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs of green fodder
    • A23K30/15—Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs of green fodder using chemicals or microorganisms for ensilaging
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/175—Amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

Definitions

  • the invention relates to the use of lysine formate in foods, in pharmaceutical and cosmetic preparations and to a process for their preparation.
  • L-Lysine as an essential amino acid, is widely used as an additive in food and feed. It is used particularly frequently for the manufacture of dietetic foods and animal feed. Lysine is also widely used in medicine, for example as a component of infusion solutions. L-lysine, for example, promotes bone growth and stimulates cell division and nucleoside synthesis.
  • L-lysine synthesized worldwide is used for the production of animal feed, especially for the production of pig or poultry feed.
  • the use of L-lysine for the production of feed serves to supply the animals with the essential amino acid present in the deficit in the protein sources used in animal nutrition. If lysine is fed, the limit is lifted and the animals' zoo performance can be increased significantly.
  • L-lysine-HCl L-lysine monohydrochloride
  • lysine hydrochloride in poultry feed means that the animals absorb more water (US 4,919,945). This can very often lead to the undesirable so-called "wet litter” and thus to an increased risk of infection of the animals. Bird growth can also be adversely affected by increased chloride administration.
  • basic amino acids in the form of their chloride salts have a very bitter taste, which also leads to less nutrient absorption by the animals.
  • L-lysine hydrochloride when using L-lysine hydrochloride in medicine, it can cause hyperchloraemic metabolic acidosis in infusion solutions.
  • the use of such infusion solutions in patients suffering from renal insufficiency leads to an undesirable further stress on the already disturbed electrolyte balance of the patient by the chloride ions.
  • the use of L-lysine in the form of the free Base is problematic in infusion solutions due to the basic pH.
  • L-lysine in the form of the free base leads to acid-base problems.
  • the high pH of the free base can lead to a Maillard reaction with sugars or isopeptide bonds in the food, particularly in the heat treatments customary for the production of feed, which leads to a reduction in the nutritional value of the feed.
  • WO 96/40618 describes concentrated aqueous lysine propionate solutions and their use in animal feed. Despite the use of very concentrated solutions, the addition of the lysopropionate brings a considerable amount of water into the feed. This results in wetter products that can spoil more easily and may need to be dried.
  • L-lysine propionate is claimed by US 3,0224,272.
  • the claimed L-lysine propionate shows good fungicidal activity. It is therefore used, as can be seen from the description, for the preservation of baked goods or other foods intended for humans, which can be spoiled by the action of fungi.
  • a disadvantage of the use of L-lysine propionate is that the propionic acid present in the salt has only a weak bacteriostatic or bacteriocidal effect and the spoilage of food can only be insufficiently prevented by the action of bacteria.
  • the object was therefore to provide a solid or liquid L-lysine salt which does not have the disadvantages mentioned above and which has a high nutritional effect with a high and / or permanent biocidal and / or biostatic effect.
  • the solid end product should also have good storage and Have processing properties. It should advantageously be able to be produced in a more solid form than in a liquid form.
  • the lysm formates produced from L-lysm formate, D-lysm formate or DL-lysine formate for the use according to the invention advantageously contain one mole of lysine per one mole of formic acid.
  • Lysm formic acid salts can also be prepared which contain more or less than one mole of formic acid per mole of lysine.
  • the lysine formates are preferably produced from L-Lysm.
  • Liquid lysiformates can also formic acid in excess if necessary. m neutralized form or lysine in excess.
  • the solid or liquid lysine formates can contain further salts of formic acid, such as alkali, alkaline earth, iron or ammonium salts.
  • Lysine sources for the production of lysine formates are, for example, proteins from which L-lysine can be obtained by hydrolysis with acids.
  • D, L-Lysm and, through subsequent resolution, also L-Lysm and D-Lysm are accessible via chemical synthesis, for example from DL- ⁇ -.Am ⁇ no- ⁇ -caprolactam.
  • L-Lysm is usually obtained via a fermentative process with the aid of microorganisms essentially of the genera Corynebacteriu, Brevibacte ⁇ um, Arthorbacter, Microbacterium, Bacillus or Nocardia and a subsequent purification, advantageously via an ion exchanger.
  • the fermentation broth can be added to the ion exchanger directly or after the biomass has been separated off.
  • Microbiological processes for the production of L-Lysm are described, for example, in Trends of Biotechnology 1 (1983: 70-74).
  • the lysine bound to the ion exchanger is advantageously eluted from the cation exchanger with formic acid, concentrated and optionally dried.
  • the fermentatively produced Lysm is usually bound to an anion exchanger and eluted with ammonia or another base.
  • the counterion can then advantageously be wholly or partly, for example, by electodialysis or, in the case of NH 3 as base, by stripping to produce the
  • Lysine formates are separated.
  • the lysine formate solutions thus produced contain at least 0.1 molar equivalents of formic acid, preferably 0.5 to 5 molar equivalents of formic acid per molar equivalent of lysine.
  • These lysine formate solutions particularly preferably contain lysine and .formic acid in stoichiometric amounts.
  • the lysine formate solutions can also contain further alkali metal or alkaline earth metal salts and / or ammonium salts of formic acid which arise, for example, from the neutralization of the base which has not been completely removed and which was used to elute the lysine from the ion exchanger. These solutions can also contain an excess of formic acid.
  • Solid lysine formates can be produced from the above-mentioned liquid lysine formate solutions by crystallization and / or by concentration and / or drying methods known to those skilled in the art, such as spray drying or fluidized-bed drying methods.
  • Lysine formates can also advantageously be prepared starting from aqueous lysine solutions or from solid lysine which contain lysine in the form of the free base by adding .formic acid. The solutions obtained are then advantageously concentrated in vacuo with heating, which produces either a concentrate or a solid product.
  • the formic acid component has a preservative effect, which protects the feed from microbial spoilage and, due to its bactericidal properties, can improve performance and health, particularly in young animals such as piglets.
  • the formic acid component in the lysine formates has no or only a very slight corrosive effect.
  • the lysine formates are odorless to slightly smelling, which means that a pungent formic acid odor cannot be detected. The product is therefore very easy to handle.
  • the lysine formates are advantageously used in foods, preferably in animal nutrition, particularly preferably as an additive in feed for pigs, piglets and poultry, such as, for example, laying hens, broilers or turkeys.
  • You can use all common animal feed such as compound feed and / or individual feed such as feed - cereals such as wheat, oats, rye, barley and legumes, Corn or "corn cob mix” can be added.
  • the lysine formates can be added directly to the feed or in the form of so-called "premixes" in which they have been mixed with other feed additives before use.
  • auxiliaries customary in agriculture such as flavorings, colorants, appetite stimulants, antibiotics, probiotics and / or enzymes, can be added to the lysine formates as auxiliary substances.
  • the auxiliaries are advantageously added in an amount of 0.1% by weight to 50% by weight, based on the weight of the lysine formates, preferably in an amount of 0.1 to 10% by weight.
  • lysine formates are advantageous. As a rule, an addition of 0.1 - 10 kg per tonne of animal feed is sufficient for lysine supplementation and successful consumption.
  • the lysine formates are preferably added in amounts of 0.5-5 kg per ton of animal feed.
  • the lysine formates can be used for the production of the feed or feed mixtures in a manner known per se.
  • the feed can be added directly after harvesting or after storage.
  • the solid and / or liquid lysine formates can be added to the feed directly or in the form of premixes, advantageously during pelleting or extrusion of the feed via, for example, a metering device. Spraying the feed or premixes with lysine formate solutions is also possible.
  • the Lysinformiate ve * can be rwendet.
  • the lysine formates can be added to all customary pharmaceutical preparations which are suitable for oral or parenteral (subcutaneous, intravenous, intramuscular, intra-perotoneal) administration. Use in parenterals is preferred.
  • pharmaceutical or cosmetic preparations are to be understood to mean all common galenical application forms, whether solid or liquid, such as tablets, film-coated tablets, capsules, powders, granules, dragees, suppositories, solutions, ointments, creams or sprays. These are manufactured in the usual way.
  • the pharmaceutical or cosmetic preparations can also contain other active ingredients, preservatives, loose agents, stabilizers, wetting agents, emulsifiers, sweeteners, colorants, flavoring agents. Contain salts for changing the osmotic pressure, buffers, coating agents and / or anti-oxidants.
  • the line-free solution was absorbed on an Amberlite 252H catalyst exchanger and washed with three column volumes of water. The column was then eluted with formic acid (85% in water). An eluate of the following composition was obtained:
  • Example 1 The solution produced according to Example 1 was brought to a final concentration of 50% Lysm and 23.6% formic acid by concentration in vacuo and then analyzed. After a long storage period or storage at 4 degrees Celsius, the solution produced in this way increased crystallization. If such a solution was evaporated to dryness in vacuo, the result was a constant. Formic acid value of 15.7 g. Formic acid. The NMR analysis of these crystals is shown in Table I.
  • Lysm x HC1 (Luta ® -Lysm)
  • an HCl-free Lysm-Base solution (50% m water) was generated from an aqueous solution of Lysm x HC1 by electrodialysis.
  • commercial Lys base (Fluka) with water was made into a 50% solution.
  • the absolute value of the Lysm content does not play a special role.
  • the Lysm content can be determined very easily from the weight used, assuming solid Lysm, if solutions were concentrated, an experimental water determination was carried out to analyze the mathematical determination.
  • a solution thus obtained with a defined lysine content was then mixed with at least one molar equivalent of formic acid and concentrated to constant weight in a vacuum with heating.
  • the solid obtained after the concentration was the desired lysm formate, which no longer had to be purified.
  • a Lys solution produced according to Example 1 was subjected to a conventional workup.
  • the fermentation broth was adsorbed on Dowex50 ion exchangers, washed with water and eluted with NH 3 solution.
  • the proportion of NH3 and additional water were removed from the eluate by means of vacuum and heating.
  • a 38.4% Lys base solution in water was then obtained. This was mixed with stochiometric amounts of .2ime ⁇ sensaure, concentrated to 50% lysm content and analyzed.
  • a lysformate composition was determined which corresponded to the lys formates mentioned in Example 1 (Tables I, I and II).
  • Example 5 Feeding trial with piglets
  • the experiment was carried out with 48 piglets (Deutsche Landrasse x Pietram). The animals were 30 days old at the start of the experiment and had an average live weight of 7.6 kg. The animals came from 9 litters, with 5 animals selected from the litter, which were randomly distributed to the 5 treatment groups according to the principle of block formation. Groups I, II and IV were assigned an additional animal from a litter. The effectiveness of the two lysing preparations used (L-Lysm x HC1 and Lysmformiat) was examined according to the treatment scheme shown in Table II. Table II: experimental groups and lysine supplement
  • Group I as a negative control received the basic feed without any lysine supplement.
  • group II, and III to the base feed were 0.12 and 0.24% lysine equivalents in the form of the commercial product Luta-lysine ®: added (L-lysine HCI x,> 78% L-Lysine, sales BASF AG, Ludwigsha-fen) .
  • groups IV and V 0.12 and 0.24% lysine equivalents were also supplemented with the test substance L-lysine formate.
  • the lysine formate prepared according to Example 1 or 2 contained 75% lysine activity and a formate content of 25%.
  • the composition of the basic feed used is shown in Table III.
  • lysine By using components that are customary in practice but low in lysine, the aim was to achieve a low base content of lysine, which should only cover about 60% of the lysine requirement of the piglets. This should create good conditions for measuring the effectiveness of the lysine supplements.
  • the basic feed was supplemented with DL-methionine and L-threonine in order to ensure a supply of these amino acids that was appropriate to the needs and thus lysine had a clearly first-limiting effect.
  • the piglets were kept in a fully air-conditioned test house in individual pens in a cage system.
  • the room temperature was 26 ° C at the start of the test and was continuously reduced to 22 ° C by the end of the test.
  • the relative humidity was between 50-60%.
  • the feed was presented to the animals for ad libitum intake.
  • the feed troughs were replenished daily, feed not consumed was weighed out on the 3rd and 7th day of each week.
  • the daily consumption of food was determined from the feed template and the back weight.
  • the animals were Position of the live mass weighed.
  • the feed conversion was determined from feed consumption and live mass gain (g feed per g gain).
  • the experimental data obtained was subjected to an analysis of variance, checked for significance (F-test) and the mean values of the individual groups compared with each other using the Student-Newman-Keuls test.
  • the result table contains the mean values and the standard deviation of the individual values. Significant differences between the mean values (P ⁇ 0.05) were marked with different capital letters.
  • the slope ratio technique was used to determine the relative biological effectiveness of the two forms of lysine used using linear regressions.
  • Table V summarizes the results of weight development, feed intake and feed conversion.
  • the animals in group I showed significantly worse weight gain, feed intake and feed utilization than the animals in the groups supplemented with lysine. Accordingly, there was a significant undersupply of lysine in the basic feed.
  • the addition of 0.12% and 0.24% lysine in the form of L-lysine x HCI significantly increased the daily gain from 214 g to 308 and 354 g, respectively by 44% and 63% compared to control group I.
  • the corresponding addition of the product lysmformate also significantly improved the daily gain to 330 g and 367 g, respectively by 54% and 72% compared to the negative control.
  • the lysine formate thus showed a greater increase in growth than the addition of L-lysine x HCI.
  • the feed consumption of the piglets was also significantly influenced by the lysine supply.
  • 0.12% and 0.24% lysine in the form of lysine x HCI was added, the piglets ingested 21% and 30% more feed than the animals that received the basic feed (group I).
  • the feed intake when using the lysine formate was 30% and 33% above the level of the base group.
  • the somewhat higher feed consumption in the groups with the addition of the lysine formate suggests good acceptance of the feed supplemented with this lysine source.
  • the negative control represents the additive constant of the regression equation, since its lysine uptake is entered with 0.
  • the variable supplemented lysine intake enables a comparison of the substances based on the same lysine intake. The influence of different feed intake is eliminated.

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Abstract

L'invention concerne l'utilisation de formiate de lysine dans des produits alimentaires, ainsi que des préparations pharmaceutiques et cosmétiques. L'invention concerne également un procédé pour produire ledit formiate de lysine, dans lequel on procède à l'élution de la lysine à l'aide d'un échangeur ionique.
PCT/EP1998/007437 1997-12-02 1998-11-19 Procede pour la production et l'utilisation de formiate de lysine Ceased WO1999027799A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU17558/99A AU1755899A (en) 1997-12-02 1998-11-19 Method for producing and using lysine formiate

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19753321A DE19753321A1 (de) 1997-12-02 1997-12-02 Verfahren zur Herstellung und Verwendung von Lysinformiat
DE19753321.3 1997-12-02

Publications (1)

Publication Number Publication Date
WO1999027799A1 true WO1999027799A1 (fr) 1999-06-10

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1998/007437 Ceased WO1999027799A1 (fr) 1997-12-02 1998-11-19 Procede pour la production et l'utilisation de formiate de lysine

Country Status (3)

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AU (1) AU1755899A (fr)
DE (1) DE19753321A1 (fr)
WO (1) WO1999027799A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1035109A1 (fr) * 1999-03-11 2000-09-13 Ajinomoto Co., Inc. Solutions aqueuses de lysine
EP1242067B1 (fr) * 1999-12-22 2006-07-26 Wisconsin Alumni Research Foundation Formate de calcium comme complement alimentaire

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3024272A (en) * 1958-04-22 1962-03-06 Du Pont Organic acid salts of basic amino acids and their use
EP0069659A1 (fr) * 1981-07-03 1983-01-12 CHANY, Charles Médicament comprenant le produit de la réaction d'un acide carboxylique sur un amino-acide basique
US4919945A (en) * 1982-11-18 1990-04-24 Degussa Aktiengesellschaft Use of Aqueous L-lysine solutions for supplementing feeds and indistrially produced mixed feeds with L-lysine
WO1996040618A2 (fr) * 1995-06-07 1996-12-19 Novus International, Inc. Solution aqueuse concentree de propionate de lysine et son procede de preparation

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3024272A (en) * 1958-04-22 1962-03-06 Du Pont Organic acid salts of basic amino acids and their use
EP0069659A1 (fr) * 1981-07-03 1983-01-12 CHANY, Charles Médicament comprenant le produit de la réaction d'un acide carboxylique sur un amino-acide basique
US4919945A (en) * 1982-11-18 1990-04-24 Degussa Aktiengesellschaft Use of Aqueous L-lysine solutions for supplementing feeds and indistrially produced mixed feeds with L-lysine
WO1996040618A2 (fr) * 1995-06-07 1996-12-19 Novus International, Inc. Solution aqueuse concentree de propionate de lysine et son procede de preparation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
EDMONDS M.: "Effect of excess levels of methionine , tryptophan , arginine , lysine or threonine on growth and dietary choice in the pig", J.ANIM. SCI., vol. 65, 1987, pages 179 - 185, XP002098735 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1035109A1 (fr) * 1999-03-11 2000-09-13 Ajinomoto Co., Inc. Solutions aqueuses de lysine
US6329548B1 (en) 1999-03-11 2001-12-11 Ajinomoto Co., Inc. Aqueous stable lysine solution
EP1242067B1 (fr) * 1999-12-22 2006-07-26 Wisconsin Alumni Research Foundation Formate de calcium comme complement alimentaire

Also Published As

Publication number Publication date
DE19753321A1 (de) 1999-06-10
AU1755899A (en) 1999-06-16

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