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Derivatives of seleno-amino acids

a technology of seleno-amino acids and derivatives, which is applied in the field of seleno-amino acids derivatives, can solve the problems of liver necrosis, synthetic l-selenomethionine has not been commercially available at reasonable prices for use as feed ingredient in livestock production, and the synthetic l-selenomethionine has not been commercially available at reasonable prices, so as to improve the stability of seleno-amino

Inactive Publication Date: 2008-12-18
ZINPRO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent describes the creation of new forms of selenium that can be added to food for humans and livestock. These new forms have better properties than the original selenium, making them easier to absorb and use by the body. They are made by combining selenium with other amino acids.

Problems solved by technology

These researchers observed that rats developed liver necrosis when fed a purified diet deficient in vitamin E. However, the addition of selenium to the diet prevented the development of this condition.
However, synthetic L-selenomethionine has not been commercially available at reasonable prices for use as feed ingredient in livestock production.
The concentration of organically bound selenium in yeast is limited by its ability to form L-selenomethionine from the selenite enriched media.
Secondly, since the organically bound selenium in yeast is produced by a biological process that is vulnerable to subtle variations in the large scale production process, the exact composition of the selenium compounds is variable and is not readily known.
These amino acids however have low water solubility and their crystals have water repellent properties that result in low rate of dissolution.
Low solubility and slow rate of dissolution lower the bioavailability of these compounds after feeding to animals.
However, it is recognized that the bioavailability of these compounds may be significantly diminished by the nutritional status of the animal and the composition of the diet and gastrointestinal tract contents.

Method used

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  • Derivatives of seleno-amino acids
  • Derivatives of seleno-amino acids
  • Derivatives of seleno-amino acids

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of L-Selenomethionine Isopropyl Ester Hydrochloride (Compound 1)

[0030]In a 1000-ml round bottom flask was added isopropyl alcohol (150 ml). The flask was placed in an ice-water bath and concentrated sulfuric acid (43.208 g of Technical grade minimum 93%) was carefully added dropwise with constant agitation. L-Selenomethionine (66.962 g, 0.338 moles) was carefully added with continued agitation. A Soxhlet extraction tube was attached to the top of the flask. A glass extraction thimble with a fritted disc is filled with Molecular Sieves 3A was placed in the extraction tube. Isopropyl alcohol was added to fill the extraction tube. A reflux condenser was attached to the extraction tube. The mixture is heated by a heating mantle to cause gentle reflux of the isopropyl alcohol. The reaction mixture was heated under reflux for 48 hrs. The heating was discontinued and the flask was placed in an ice-water bath. Ammonium hydroxide solution is added slowly with continued mixing. A ...

example 2

Preparation of N-Succinyl L-Selenomethionine (Compound 2)

[0033]A 3-neck 250-ml round bottom flask was equipped with a thermometer, a reflux condenser and an addition funnel. Ethyl acetate (75 ml) was placed into the flask. Succinic anhydride (12.404 g) was finely pulverized in a mortar and added to the ethyl acetate in the flask. The mixture was stirred by a magnetic stirrer until all solids dissolved. L-Selenomethionine (19.630 g, 0.1 mole) was added. Dilute sulfuric acid (1.0 ml of a solution obtained by diluting 1 part concentrated sulfuric acid with 5 parts water). The mixture was heated under reflux with continued stirring for 1 hr. The hot clear solution was filtered. A white crystalline precipitate was formed as the filtrate was cooled. The precipitate weighed 24.92 g (84.14% yield).

[0034]The FTIR spectrum of the finely ground crystals obtained above in a potassium bromide pellet showed absorption peaks at about: 3313.5(m), 3091.7(w), 2931.6(m), 2626.9(w), 1714.6(vs), 1647.1(...

example 3

Preparation of N-Carbamoyl L-Selenomethionine (Compound 3)

[0036]A 3-neck 250-ml round bottom flask was equipped with a thermometer, a reflux condenser and an addition funnel. Water (40 ml) was placed into the flask. Potassium cyanate (9.735 g, 0.115 moles) was added to the water in the flask and the cold mixture was stirred by a magnetic stirrer until all solids dissolved. L-Selenomethionine (19.815 g, 0.1 moles) was added. The mixture was heated under reflux with vigorous stirring. The inside temperature reached 94° C. and then lowered to 80-85° C. The reaction mixture was maintained at 80-85° C. for 2 hrs. The clear solution obtained was cooled to room temperature. Hydrochloric acid (11.272 g, 0.115 moles) was added slowly with continued stirring. A heavy white crystalline precipitate was formed and filtered under reduced pressure. The precipitate weighed 20 g (83.65% yield).

[0037]The FTIR spectrum of the finely ground crystals obtained above in a potassium bromide pellet showed a...

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Abstract

Derivatives of seleno-alpha amino acids, particularly selenomethionine as enhanced bioavailable sources of selenium in animal diets.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application is a Divisional Application of U.S. Ser. No. 11 / 181,264 filed on Jul. 14, 2005, herein incorporated by reference in its entirety.BACKGROUND OF THE INVENTION[0002]The essential role of selenium in nutrition was first recognized by Schwarz and Foltz in 1957 (Schwarz, K. and Foltz, C. M., Selenium as an integral part of factor 3 against dietary necrotic liver degeneration. J. Am. Chem. Soc. 79:3292 (1957)). These researchers observed that rats developed liver necrosis when fed a purified diet deficient in vitamin E. However, the addition of selenium to the diet prevented the development of this condition. The ability of dietary selenium to prevent the development of exudative diathesis, a condition characterized by leakage of plasma into subcutaneous spaces of the abdomen and breast in chicken, was reported in the same year by Patterson et al (Patterson, E. L., Milstrey, R., Stokstad, E. L. R. Effect of selenium in preventin...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A23K1/16
CPCA23L1/3051C07D233/76C07C391/00A23L33/175A61P3/00A61P43/00
Inventor ABDEL-MONEM, MAHMOUD M.ANDERSON, MICHAEL D.
Owner ZINPRO