Oligosaccharide ingredient. RU patent 2497827.

IPC classes for russian patent Oligosaccharide ingredient. RU patent 2497827. (RU 2497827):

C07H3/06 - Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages

C07H3/04 - Disaccharides

A23L1/30 - containing additives (A23L0001308000 takes precedence);;

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FIELD: chemistry.

SUBSTANCE: oligosaccharide ingredient, which is intended to increase content of sialic acid in baby formula, contains glycosylated amino acids and peptides of general formula R_nSac_m, where R is an amino acid residue, Sac is a monosaccharide selected from a group comprising N-acetyl-neuraminic acid, N-acetyl galactosamine and galactose n has a value from 1 to 10, under the condition that if n=1, then R is a threonine residue or a serine residue and if n has a value between (2) and (10) the peptide contains at least one threonine or serine residue, m has a value from 2 to 4 and at least 20 mol % of the ingredient is N-acetyl-neuraminic acid, where the oligosaccharide component contains 10-25 mol % N-acetyl galactosamine, 10-25 mol % galactose, 20-50 mol % N-acetyl-neuraminic acid and 15-50 mol % threonine or serine or mixture thereof.

EFFECT: obtaining an oligosaccharide ingredient intended for increasing content of sialic acid in baby formula.

6 cl, 2 ex

The technical field to which the invention relates

The present invention relates to ingredient with a high content of acid, food containing the specified ingredient, and methods of production specified ingredient.

The level of technology

It is known that breast milk contains a large number of not digested oligosaccharides. Actually oligosaccharides are the third largest solid component (after lactose and lipids) breast milk and are contained in the colostrum in concentration 12-15 g/l in Mature milk in concentrations of 5 to 8 g/HP Oligosaccharides breast milk is very resistant to enzymatic hydrolysis, which suggests that these oligosaccharides can be vital functions not directly related to their energy value.

Over the last two decades chemical structure of oligosaccharides of breast milk were studied by NMR spectroscopy and mass spectrometry. Every single oligosaccharide is based on a combination of glucose, galactose, acid (N- acid), fucose and/or N-, which are connected in many different ways, which leads to a huge number of different oligosaccharides in breast-milk - so far identified more than 130 such structures. Almost all of them have a fragment of lactose at pampering end, while acid (in case of its presence) takes the terminal position at the end.

Of particular interest is a large number of oligosaccharides in breast milk. acid is a sugar, which is a vital structural and functional component of brain. It is believed that it plays an important role in the momentum transfer of nerve cells, the formation of memory and contacts between the cells. Research on the offspring of rats showed that supplements acid at an early age increase content acid in brain and improve the learning ability of well-nourished, and bad eating animals, and that these changes are persisted into adulthood.

Breast milk is recommended for all infants. However, in some cases, breastfeeding is not enough or it has unsuccessfully for medical reasons, or the mother chooses not to breastfeed. For such cases were developed infant. However, cow's milk, which is usually used as a basis for commercially available mixtures for baby food, has a much smaller content oligosaccharides compared with the mother's milk. As the breast milk composition and functions of the individual components are becoming better understood, it becomes apparent that it may be desirable to increase the content of acids in infant formula based on cow's milk.

There are several known sources acid, including a free N- acid, and other oligosaccharides containing acid gangliosides and protein . or CGMP is a large, rich in carbohydrates hydrophilic protein, the C-terminal fragment to-casein, from which it can be split enzymatically or by processing the acid. The application US 2005/0096295 is proposed to increase the content of acids in infant formula by inserting a new CGMP ingredient, has increased concentration acid. This ingredient has content acid above 60 mg/g of protein, compared to 40-60 mg/g of protein in the natural CGMP. It can be either fractionation using anionic chromatography or partial hydrolysis with subsequent fractionation using anionic chromatography.

However, there remains a need to obtain other ingredients, rich acid, which can be used for the enrichment of infant formula and other nutrient composition specified an important component.

The essence of the invention

In the present invention described ingredient containing glycosylated amino acids and proteins General formula R n Sac m , where R represents the balance of amino acids, Sac is a monosaccharide, selected from the group consisting of N- acid, N-atsetilgalaktozamin and galactose, n is from 1 to 10, provided that if n=1, R represents the balance of threonine or serine residue, and if n has a value from 2 to 10, peptide contains at least one balance or serine threonine, m has a value from 2 to 4, and at least 20 mol.% this ingredient is a N- acid.

Described ingredient is a new ingredient in the food category of quality, rich acid, which can be used to add to the nutrient compositions, such as mixtures for baby food, to increase the content of acid composition.

The present invention also covers a method of production ingredient containing glycosylated amino acids and proteins General formula R n Sac m , where R represents the balance of amino acids, Sac is a monosaccharide, selected from the group contains N- acid, N-atsetilgalaktozamin and galactose, n is from 1 to 10, provided that if n=1, R represents the balance of threonine or serine residue, and if n has a value from 2 to 10, peptide contains at least one balance or serine threonine, m has a value from 2 to 4, and at least 20 mol.% this ingredient is a N- acid, including the stage of hydrolysis using and obtaining a mixture of amino acids and proteins with chain length from 2 to 10, and nanofiltration received hydrolyzed mixture with holding the faction having a molecular weight of 1000-2000 Yes.

The present invention also covers food product containing described above ingredient. In particular, the food is a baby food or infant formula, but this product can be any type of food or drink, abused children, babies or adults. The use of a food product, containing such ingredient can improve the integration of acid gangliosides in the brain, thus improving the relevant function of the neurons, such as .

Disclosure of the invention

In the present description of the following words have definitions that need to be taken into account when reading and interpreting descriptions, examples and claims.

"CGMP": , i.e. , which is detached from the cow to-casein under the action of the enzyme .

"Infant formula": food for a balanced diet of infants during the first 1-6 months of their life, and for the partial power after this period. This term includes the mixture for the initial period of breastfeeding, and for a subsequent period of breastfeeding.

" acid": N- acid.

In the present invention described ingredient containing glycosylated amino acids and proteins General formula R n SaC m , where R represents the balance of amino acids. Sac is a monosaccharide, selected from the group consisting of N- acid, N-atsetilgalaktozamin and galactose, n is from 1 to 10, provided that if n=1, R represents the balance of threonine or serine residue, and if n has a value from 2 to 10, peptide contains at least one balance or serine threonine, m has a value from 2 to 4, and at least 20 mol.% this ingredient represents the N- acid, as well as food products for children or adults, containing such ingredient.

Preferably, n has a value of 1 to 3 and m is set to 3 or 4.

Described ingredient contains at least 20 mol.% acid as part of chain associated with hydroxyl group or serine threonine. acid may form part of the chain or may itself be a Deputy fragment in the chain. So, ingredient may contain the following monosaccharides:

Connection

Mol.%

N-atsetilgalaktozamin (GalNAc)

10-25

Galactose (Gal),

10-25

N- acid (NeuAc)

50-20

ingredient may contain from 15 to 50 mol.% a mixture of serine and/or threonine.

ingredient may contain the following glycosylated amino acids or peptides:

NeuAc-a-2,3-Gal-beta-l,3-(NeuAc-alpha-2,6-)-GalNAc-R n

NeuAc-a-2,3-Gal-beta-1,3-GalNAc-R n

Gal-beta-l,3-(NeuAc-alpha-2,6-)-GalNAc-R n

Gal-beta-l,3-GalNAc-R n

ingredient according to the present invention can be receive hydrolysis of CGMP using and obtaining a mixture of amino acids and proteins with chain length from 2 to 10, and received hydrolyzed mixture with holding the faction having a molecular weight of 1000 - 2000 Dalton.

CGMP itself is a by-product of cheese making, in which milk is treated by enzyme for the deposition of casein. In this process, CGMP is detached from casein and remains in solution with whey protein. This product is known as sweet whey. CGMP can be separated from whey protein by any method known in the art. Suitable method is described in the patent EP 986312.

Hydrolysis can be carried out with any suitable combination of enzymes. One example of a commercially available enzyme systems with Exo - and activity is the product, sold under the brand Flavourzyme® Department Novozymes company Novo Nordisk.

In the preferred aspect of the present invention described above ingredient enter in the composition of the food. In the context of the present invention, the term «food product» covers any suitable to-eat products. Thus, it can be the product intended for human consumption, in particular mixture for nutrition of infants mixture for later feeding, baby food, such as porridge for feeding babies, etc. In particular, ingredient according to the present invention can be included into the composition of mixtures for infant milk substitutes for children 1-3 years and dried milk or cereal mixtures.

Food can be prepared in any way, well-known in the art, in accordance with the type of product, and ingredient according to the present invention can be added to the product at the appropriate stage of the production process. For example, a mixture for nutrition of infants can be prepared by mixing in suitable proportions source of protein, any of carbohydrates, non-lactose, and source of fat. If desired, you can add emulsifiers. At this point you can add vitamins and minerals, but they usually add later to avoid thermal destruction. Any lipophilic vitamins, emulsifiers, etc. before mixing dissolving in the source of fats. You can then add water, preferably passed through reverse osmosis, for the formation of the liquid mixture.

The received liquid mixture then can be processed thermally to reduce levels of bacteria. For example, the liquid mixture, you can quickly heat up to a temperature in the range of approximately 80 C to about 110 degrees With the period of time from about 5 seconds until about 5 minutes. This can be done injection of steam or heat exchanger, such as plate heat exchanger.

Then the liquid mixture can be cooled to a temperature of about 60 C up to about 85 C, for example, by an instantaneous cooling. Then the liquid mixture can be homogenized, for example, in two stages: at a pressure of about 7 MPa up to about 40 MPa at the first stage, and from about 2 MPa to about 14 MPa at the second stage. mixture you can then cool to add components such as vitamins and minerals. Usually at this time of the pH values and the content of dry substances in a homogenized mixture traditionally lead to default values.

mixture is transferred to the appropriate dryer, such as spray dryer or freeze-dryer, and converted into a powder. The resulting powder must have a moisture content of less than about 5 wt.%.

ingredient according to the present invention can be added directly to an infant formula dry mixture, or, if the mixture is a liquid consistence, on the one described above stage of mixing. In both cases, a qualified specialist will be clear that the addition of this ingredient entails simultaneous adding some amino nitrogen, and may therefore be necessary to adjust the content of protein in baby formula or other products, which is added the ingredient in question. The resolved content of protein and amino acid profile mixtures for baby food are specified in legislation such as the European Commission Directive 91/3 21/EEC of 14 may 1991, and the skilled specialist in this field can easily adjust the content of protein and amino acid profile infant with the additional amino nitrogen input with the ingredient of the present invention, as well as additional content, and serine threonine.

The final concentration of ingredient in the food product for feeding children or infants can range from 0.2 to 4.0% preferably from 0.5 to 2.0 wt.% to the mass of dry substances. But the values given should not be considered as limiting, and you have to adapt them for specific target audiences, for example, based on the weight and age or state of health of a child or infant. Preferably, the mixture or food product containing ingredient of the present invention, give child at each feeding.

Although preferable to making the described additives in foodstuffs and products for nutrition of children or infants, a positive effect can give adding described additives in food products that do not have a specific target audience, or in food products for adults. For example, ingredient according to the present invention can be entered in the composition of food products for patients and food for the elderly. Such foods may include, among others, milk, yogurt, cottage cheese, cheese, sour-milk products, fermented milk products, ice-cream, fermented products based on cereals or milk-based products. In addition ingredient according to the present invention food product, such as infant formula can contain one or more additional oligosaccharides, which add separately.

Below is an example of the composition of mixtures for baby food containing ingredient according to the present invention.

Nutrient 100 kcal 1 liter

Energy (kcal)

100 670

Protein (g)

1,83 12,3 Fat (g) 5,3 35,7

Linoleic acid (g)

0,79 5,3

α-linolenic acid (mg)

101 675

Lactose (g)

11,2 74,7

ingredient(g)

0,15 1,0

Mineral substances (g)

0,37 2,5 Na (mg) 23 150 K (mg) 89 590 CL (mg) 64 430 CA (mg) 62 410 P (mg) 31 210 Mg (mg) 7 50 Mn (mcg) 8 50 Se (mcg) 2 13

Vitamin A (g RE)

105 700

Vitamin D (g)

1,5 10

Vitamin E (mg)

0,8 5,4

Vitamin K1 (mcg)

8 54

Vitamin C (mg)

10 67

Vitamin B1 (mg)

0,07 0,47

Vitamin B2 (mg)

0,15 1,0

Niacin (mg)

1 6,7

Vitamin B6 (mg)

0,075 0,50

Folic acid (mcg)

9 60

Pantothenic acid (mg)

0,45 3

Vitamin B12 (g)

0,3 2

Biotin (mcg)

2,2 15

Choline (mg)

10 67 Fe (mg) 1,2 8 I(mcg) 15 100 Cu (mg) 0,06 0,4 Zn (mg) 0,75 5

Example 2

50 g (Biopure GMP, Davisco, USA) dissolved at a concentration of 10% (wt./about.) in 500 ml of deionized water. The resulting solution was heated up within 30 minutes at 40 C with careful hashing and recycling through a laboratory system of the tangential flow filtration (Millipore, USA) with one filter cassette Pellicon 1000 daltons (0.1 m 3 ) for the inlet pressure of 1.2 bar and without pressure .

Then add the from Aspergillus oryzae (Flavourzyme 1000L containing 1000 units of amino peptidases per gram (LAPU/r), Novozymes, Denmark) in the quantity of 3500 LAPU 50 g of protein. After about an hour started , increasing pressure up to 3 bar pressure at inlet pressure 3 bar. After 5 hours stopped filtering and collected . and 7 fractions of leachate collected during the process, . Then determined the content of dry residue (DM) acid in each fraction. Contents acid was determined after a soft acidic hydrolysis and the introduction of a label by using the method DMB (1.2-diamino-4,5- digidrohlorid) and HPLC analysis on a device with a reversed-phase column Shodex 18 and FLD, using authentic NeuAc as an external standard. Table 1 provides a mass balance and content acid in the source material, fractions of leachate and .

Table 1

Weight (g)

NeuAc (% of dry substance)

Output (%)

enrichment

Source material

50 7,5 100 1,00

The filtrate 1

4,32 0,2 8,64 0,03

The filtrate 2

3,1 0,2 6,2 0,02

The filtrate 3

6,1 0,3 12,2 0,04

The filtrate 4

4,29 1,4 8,58 0,18

The filtrate 5

3,56 0,8 7,12 0,10

The filtrate 6

2,8 0,4 5,6 0,05

The filtrate 7

2,94 0,3 5,88 0,04

22,6 14.4 45,2 1,92

The content of galactose and N- in determined after acid hydrolysis by high performance anion-exchange chromatography () with use of the analytical column Dionex CarboPac PA1 and pulse detector. In short, dissolved in water and add acid to the final concentration of 2M. The solution was heated for 3 hours at 100 C, dried in a stream of nitrogen and again dissolved in water. Sample analyzed after filtration through the fine filter with a pore size of 22 microns. Quantitative assessment was performed using authentic galactose and (N-atsetilgalaktozamin turns into while processing acid) as external standards. Threonine quantitatively determined by HPLC after acid hydrolysis 6 N. 1.

The final dried product contained 29,6% Mas. (NeuAc) 2-3-Gal-GalNAc-Thr with the structure of NeuAc-a-2,3-Gal-beta-l,3-(NeuAc-alpha-2,6-)-GalNAc-threonine/a peptide with 30 mol.% acid, 15 mol.% galactose, 13 mol.% N- and 42 mol.% threonine.

1. ingredient designed to increase the content of acid mixtures for baby food containing glycosylated amino acids and peptides General formula R n Sac m , where R is the remainder amino acids, Sac is , selected from the group consisting of N- acid, N-atsetilgalaktozamin and galactose, n is from 1 to 10, provided that if n=1, R is the remainder or serine threonine, if n has a value from 2 to 10, the peptide contains at least one balance or serine threonine, m has a value from 2 to 4 and N- acid is at least 20 mol.% ingredient, where component contains from 10 to 25 mol.% N-, from 10 to 25 mol.% galactose, from 20 to 50 mol.% N- acid and from 15 to 50 mol.% or serine threonine or their mixture.

2. ingredient according to claim 1, where n is from 1 to 3.

3. ingredient according to claim 1, where m is set to 2 or 3.

4. Infant formula containing ingredient for any one of claims 1 to 3.

5. Infant formula according to claim 4, which contains from 0.2 to 4.0% by wt ingredient.