CN102627584A - Carbamyl glycine dipeptide chelated copper and preparation method thereof - Google Patents
Carbamyl glycine dipeptide chelated copper and preparation method thereof Download PDFInfo
- Publication number
- CN102627584A CN102627584A CN201210081843XA CN201210081843A CN102627584A CN 102627584 A CN102627584 A CN 102627584A CN 201210081843X A CN201210081843X A CN 201210081843XA CN 201210081843 A CN201210081843 A CN 201210081843A CN 102627584 A CN102627584 A CN 102627584A
- Authority
- CN
- China
- Prior art keywords
- carbamoylglycine
- copper
- preparation
- peptide chelated
- dipeptides
- 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.)
- Pending
Links
Images
Abstract
The invention discloses a novel dipeptide chelate carbamyl glycine dipeptide chelated copper, with a molecular formula of C6H10N4O6Cu and a structural formula shown as (I). The carbamyl glycine dipeptide chelated copper shows high absorption rate and high absorption strength in animals, can be used as animal feed additives to supplement copper element in dietary and improve the growth performance and immune function of animals. The invention also provides a preparation method of the carbamoyl glycine dipeptide chelated copper. The method has the advantages of simple process, high product purity, stable quality, and is suitable for industrial application.
Description
Technical field
The present invention relates to a kind of two peptide chelated coppers and preparation method thereof, be specifically related to carbamoylglycine chelated copper and preparation method thereof.
Background technology
Research shows that high-copper daily ration (100-250 mg/kg, copper sulfate) can promote the growth of pig, improves food consumption and improves very much the copper feed utilization ratio.High zinc (2000-3000 mg/kg, zinc oxide) can alleviate grice diarrhoea, promotes to grow.Therefore, high-copper, high zinc are to raise pigs at present to go up the nutrition regulation means comparatively widely of using.Yet use high-copper, high zinc, cause a large amount of copper (80%-95%) and zinc (90%-95%) to enter environment with ight soil, copper, zinc concentration increase in pig muscle and the liver simultaneously, bring direct harm to human and livestock health.Coffey (1994) is effect and the optimal dose of research Methionin chelated copper as growth stimulant; Carry out the test of 8 groups with 1301 weanling pigs; The result shows that low dosage Methionin chelated copper (100 mg/kg copper) does not have significant difference with the short fruit of coming into force of high dosage copper sulfate (250 mg/kg copper).Ward (1997a) has summed up the series of studies of associating nutrient research and technique center, and the copper that 100 mg/kg are provided with the Methionin chelated copper is to the growth promoting function of weanling pig and provide the copper of 200-250 mg/kg that same effect is arranged with copper sulfate.
Organic copper commonly used is a copper amino acid chelate in the feed at present, and it has satisfactory stability property in digestive tube, be beneficial to absorption.But, because amino acid mainly is through passive transport and depends on Na
+Active transport, shift from enteric cavity, between each seed amino acid of brush border transhipment the competition effect is arranged and pass, thereby has influenced the uptake rate and the absorption intensity of copper amino acid chelate.Thereby, research and develop that a kind of uptake rate is higher, the better organic copper of absorption intensity is the target that this area practitioner constantly makes great efforts.
Summary of the invention
The purpose of this invention is to provide a kind of two new peptide chelated copper compounds: carbamoylglycine two peptide chelated coppers.
Another object of the present invention provides the preparation method of above-mentioned carbamoylglycine two peptide chelated coppers.
Another object of the present invention provides the application of carbamoylglycine two peptide chelated coppers as fodder additives.
The technical scheme that the present invention adopted is:
Carbamoylglycine two peptide chelated coppers, its molecular formula are C
6H
10N
4O
6Cu is green powder, and is soluble in water, is insoluble to ethanol, methyl alcohol, acetone and other organic solvent, and structural formula is shown in (I):
The preparation method of carbamoylglycine two peptide chelated coppers comprises the steps
1) the carbamoylglycine dipeptides is put into reactor drum, be dissolved in water;
2) add the water hydrated barta under the stirring, be heated to 75 ~ 85 ℃;
3) continue to add copper sulfate, 70 ~ 90 ℃ were reacted 2 ~ 4 hours;
4) 70 ~ 90 ℃ of filtrations, filtrating concentrates, behind the crystallisation by cooling, drying carbamoylglycine two peptide chelated coppers.
Its synthetic route is as follows:
Preferably, in the preparation process, the mol ratio of carbamoylglycine dipeptides, hydrated barta, copper sulfate is 2 ~ 8:1 ~ 4:1 ~ 4.
Preferably, in the preparation process, carbamoylglycine dipeptides: hydrated barta: the mol ratio of copper sulfate is 2:1:1.
Preferably, the mass volume ratio of carbamoylglycine dipeptides and water is 1g:1 ~ 2ml in the step 1).
Above-described carbamoylglycine two peptide chelated coppers are as the application of fodder additives.
Beneficial effect of the present invention is:
The invention provides a kind of technical intelligence of synthesizing amino formylglycine two peptide chelated coppers, it is simple to have a synthesis technique, and raw material is easy to get; Cost is low, and product purity is higher, steady quality; Technology is convenient to advantages such as suitability for industrialized production, and resulting carbamoylglycine two peptide chelated coppers are higher than copper amino acid chelate uptake rate simultaneously, and absorption intensity is big; Can be used as animal feedstuff additive, replenish the copper in the daily ration, improve the growth performance and the immune performance of animal body.
Description of drawings
Fig. 1 is the infrared spectrogram of carbamoylglycine two peptide chelated coppers;
Fig. 2 is the infrared spectrogram of carbamoylglycine.
Embodiment
Below in conjunction with embodiment the present invention is further described, but is not limited thereto.
The preparation method of carbamoylglycine two peptide chelated coppers, its concrete steps are following:
Take by weighing 23.6g (0.2mol) carbamoylglycine dipeptides, add water 40ml, ten water hydrated barta 35.1g (0.1mol); After the heating for dissolving, add 24.9g (0.1mol) cupric sulfate pentahydrate again, controlled temperature was 70 ℃ of reactions 1 hour; Suction filtration while hot, filtrating repetition suction filtration is not to there being obvious sediment (necessary time filter), and filtrating has been concentrated into epitaxial and has occurred on rotatory evaporator; Under agitation be cooled to and separate out solid, suction filtration, solid is dried to constant weight under 105 ℃ earlier; Get carbamoylglycine two peptide chelated copper 28.7g, detecting copper content is 21.23%, and nitrogen content is 18.87%.
Embodiment 2
The preparation method of carbamoylglycine two peptide chelated coppers, its concrete steps are following:
Take by weighing 47.2g (0.4mol) carbamoylglycine dipeptides, add water 80ml, ten water hydrated barta 70.2g (0.2mol); After the heating for dissolving, add 49.8g (0.2mol) cupric sulfate pentahydrate again, controlled temperature was 80 ℃ of reactions 2 hours; Suction filtration while hot, filtrating repetition suction filtration is not to there being obvious sediment (necessary time filter), and filtrating has been concentrated into epitaxial and has occurred on rotatory evaporator; Under agitation be cooled to and separate out solid, suction filtration, solid is dried to constant weight under 105 ℃ earlier; Get carbamoylglycine two peptide chelated copper 57.6g, detecting copper content is 21.16%, and nitrogen content is 18.76%.
Embodiment 3
The preparation method of carbamoylglycine two peptide chelated coppers, its concrete steps are following:
Take by weighing 70.8g (0.6mol) carbamoylglycine dipeptides, add water 120ml, ten water hydrated barta 105.3g (0.3mol); After the heating for dissolving, add 74.7g (0.3mol) cupric sulfate pentahydrate again, controlled temperature was 90 ℃ of reactions 4 hours; Suction filtration while hot, filtrating repetition suction filtration is not to there being obvious sediment (necessary time filter), and filtrating has been concentrated into epitaxial and has occurred on rotatory evaporator; Under agitation be cooled to and separate out solid, suction filtration, solid is dried to constant weight under 105 ℃ earlier; Get carbamoylglycine two peptide chelated copper 85.4g, detecting copper content is 21.17%, and nitrogen content is 18.82%.
Embodiment 4
The preparation method of carbamoylglycine two peptide chelated coppers, its concrete steps are following:
Take by weighing 94.4g (0.8mol) carbamoylglycine dipeptides, add water 160ml, ten water hydrated barta 140.4g (0.4mol); After the heating for dissolving, add 99.6g (0.4mol) cupric sulfate pentahydrate again, controlled temperature was 90 ℃ of reactions 4 hours; Suction filtration while hot, filtrating repetition suction filtration is not to there being obvious sediment (necessary time filter), and filtrating has been concentrated into epitaxial and has occurred on rotatory evaporator; Under agitation be cooled to and separate out solid, suction filtration, solid is dried to constant weight under 105 ℃ earlier; Get carbamoylglycine two peptide chelated copper 113.6g, detecting copper content is 21.14%, and nitrogen content is 18.69%.
Embodiment 5
The preparation method of carbamoylglycine two peptide chelated coppers, its concrete steps are following:
Take by weighing 47.2g (0.4mol) carbamoylglycine dipeptides, add water 94.4ml, hydrated barta 34.2g (0.2mol); After the heating for dissolving, add 49.8g (0.2mol) cupric sulfate pentahydrate again, controlled temperature was 70 ℃ of reactions 2 hours; Suction filtration while hot, filtrating repetition suction filtration is not to there being obvious sediment (necessary time filter), and filtrating has been concentrated into epitaxial and has occurred on rotatory evaporator; Under agitation be cooled to and separate out solid, suction filtration, solid is dried to constant weight under 105 ℃ earlier; Get carbamoylglycine two peptide chelated copper 57.4g, detecting copper content is 21.19%, and nitrogen content is 18.77%.
The product that embodiment 1 obtains is used absolute ethanol washing, and oven dry can get the higher carbamoylglycine of purity two peptide chelated coppers, and molecular formula is C
6H
10N
4O
6Cu is green powder, and is soluble in water, is insoluble to ethanol, methyl alcohol, acetone and other organic solvent.Sample presentation is surveyed infrared spectrogram, the gained collection of illustrative plates as
Fig. 1Shown in, the infrared spectrogram of corresponding carbamoylglycine as
Fig. 2Shown in.This two peptide chelated coppers sample presentation carries out ultimate analysis, and Cu, C, H, N content are respectively 21.47%, 24.29%, 3.50%, 18.87% (calculated value: Cu21.50%, C24.36%, H3.41%, N18.95%).Embodiment 2 ~ 5 resulting products all obtain green powder after same treatment, soluble in water, are insoluble to ethanol, methyl alcohol, acetone and other organic solvent.Sample presentation detects, and gained infrared light collection of illustrative plates is extremely similar with Fig. 1, is characterized by same compound.The content of Cu, C, H, N is near calculated value.
Carbamoylglycine two peptide chelated coppers that the inventive method prepares can be used as animal feedstuff additive, replenish the copper in the daily ration.
Experimentation on animals:
Carry out experimentation on animals with embodiment 1 resulting carbamoylglycine two peptide chelated coppers below.
1, experiment is provided with
60 close batch, body weight 35 age in days weanling pigs close, that be in a good state of health are raised a week in advance; Be divided into 5 groups at random; 3 experimental group (adding 100ppm, 150ppm, 200ppm carbamoylglycine two peptide chelated coppers in the basal diet respectively), a negative control group (basal diet), a positive control group (basal diet adds the 200ppm glycocoll-copper); Every group of 3 repetitions, each repeats 4 pigs.
This experiment is carried out in the insulation pig house, and trial period was 8 weeks.Duration of test, free choice feeding drinking-water; Natural lighting, temperature is at 22-28 ℃, and humidity is at 60-70%.The crude protein content of basal diet is 18.0%, and metabolizable energy is 3400 Kcal/kg, and calcium contents is 0.8%, and available phosphorus content is 0.35%.
2, production performance test
Food consumption, the ight soil index of the every hurdle of time recording every day piglet; Measure the individual weight of each piglet weekly; Add up feedstuff-meat ratio weekly, calculate all food consumptions, day weight gain.
3, experimental result
Experimental result shows that the experimental group ight soil index of all interpolation carbamoylglycine two peptide chelated coppers is higher, and diarrhea piglet number is all far below negative control group, and wherein negative control group is in piglet death of duration of test.The day weight gain rate of experimental group piglet all is significantly higher than positive and negative control group (P ﹤ 0.05); The weight gain of piglets that adds 150ppm in the experimental group is the fastest, and its average growth rate is 118% of a positive control group for 137% of negative control group; Be illustrated in production performance and immune performance that carbamoylglycine two peptide chelated coppers that add 150ppm in the feed can significantly improve piglet; And improved the bioavailability of copper, and can practice thrift Mineral resources greatly, alleviate environmental stress.
More than experiment shows that in animal body, carbamoylglycine two peptide chelated coppers are higher than copper amino acid chelate uptake rate, and absorption intensity is big, can be used as animal feedstuff additive, replenishes the copper in the daily ration, improves the growth performance and the immune performance of animal body.
Claims (6)
1. carbamoylglycine two peptide chelated coppers, its molecular formula is C
6H
10N
4O
6Cu, structural formula is shown in (I):
2. the preparation method of carbamoylglycine two peptide chelated coppers comprises the steps:
1) the carbamoylglycine dipeptides is put into reactor drum, be dissolved in water;
2) stir adding hydrated barta down, be heated to 75 ~ 85 ℃;
3) continue to add copper sulfate, 70 ~ 90 ℃ were reacted 2 ~ 4 hours;
4) 70 ~ 90 ℃ of filtrations, filtrating concentrates, behind the crystallisation by cooling, drying carbamoylglycine two peptide chelated coppers.
3. preparation method according to claim 2 is characterized in that, carbamoylglycine dipeptides: hydrated barta: the mol ratio of copper sulfate is 2 ~ 8:1 ~ 4:1 ~ 4.
4. preparation method according to claim 2 is characterized in that, carbamoylglycine dipeptides: hydrated barta: the mol ratio of copper sulfate is 2:1:1.
5. preparation method according to claim 2 is characterized in that, the mass volume ratio of carbamoylglycine dipeptides and water is 1g:1 ~ 2ml in the step 1).
6. carbamoylglycine two peptide chelated coppers are as the application of fodder additives.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210081843XA CN102627584A (en) | 2012-03-26 | 2012-03-26 | Carbamyl glycine dipeptide chelated copper and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210081843XA CN102627584A (en) | 2012-03-26 | 2012-03-26 | Carbamyl glycine dipeptide chelated copper and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102627584A true CN102627584A (en) | 2012-08-08 |
Family
ID=46586010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210081843XA Pending CN102627584A (en) | 2012-03-26 | 2012-03-26 | Carbamyl glycine dipeptide chelated copper and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102627584A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113841795A (en) * | 2021-09-18 | 2021-12-28 | 广州康瑞德饲料科技有限公司 | Self-assembled small peptide chelated copper feed additive and preparation method thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4830716A (en) * | 1986-07-03 | 1989-05-16 | Albion International, Inc. | Preparation of pharmaceutical grade amino acid chelates |
| US6407138B1 (en) * | 2000-10-11 | 2002-06-18 | Albion International, Inc. | Composition and method for preparing electrically neutral amino acid chelates free of interfering ions |
| US6458981B1 (en) * | 2000-10-11 | 2002-10-01 | Albion International, Inc. | Composition and method for preparing amino acid chelate hydroxides free of interfering ions |
| CN101302171A (en) * | 2008-06-30 | 2008-11-12 | 瑞发医药股份有限公司 | Production process of pure amino acid chelate and use thereof |
| CN101671263A (en) * | 2009-10-12 | 2010-03-17 | 北京中国科学院老专家技术中心 | Method for preparing novel amino acid chelate |
| CN102093467A (en) * | 2010-11-02 | 2011-06-15 | 中国科学院亚热带农业生态研究所 | Dipeptide iron chelate for feed additives and preparation method thereof |
-
2012
- 2012-03-26 CN CN201210081843XA patent/CN102627584A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4830716A (en) * | 1986-07-03 | 1989-05-16 | Albion International, Inc. | Preparation of pharmaceutical grade amino acid chelates |
| US4830716B1 (en) * | 1986-07-03 | 1999-12-07 | Albion Int | Preparation of pharmaceutical grade amino acid chelates |
| US6407138B1 (en) * | 2000-10-11 | 2002-06-18 | Albion International, Inc. | Composition and method for preparing electrically neutral amino acid chelates free of interfering ions |
| US6458981B1 (en) * | 2000-10-11 | 2002-10-01 | Albion International, Inc. | Composition and method for preparing amino acid chelate hydroxides free of interfering ions |
| CN101302171A (en) * | 2008-06-30 | 2008-11-12 | 瑞发医药股份有限公司 | Production process of pure amino acid chelate and use thereof |
| CN101671263A (en) * | 2009-10-12 | 2010-03-17 | 北京中国科学院老专家技术中心 | Method for preparing novel amino acid chelate |
| CN102093467A (en) * | 2010-11-02 | 2011-06-15 | 中国科学院亚热带农业生态研究所 | Dipeptide iron chelate for feed additives and preparation method thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113841795A (en) * | 2021-09-18 | 2021-12-28 | 广州康瑞德饲料科技有限公司 | Self-assembled small peptide chelated copper feed additive and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103224461B (en) | Preparation method of large granule crystal form methionine metal chelate and application thereof | |
| CN102415505B (en) | Functional pellet feed for high yield cows in lactation period | |
| CN101139299B (en) | Method for preparing copper zinc aminoacetic acid complex by ball milling solid state | |
| CN101948402A (en) | Method for preparing D-calcium pantothenate | |
| CN108349871B (en) | N, N-dimethyl glycine organic acid composite salt, composition and application thereof | |
| CN101289412B (en) | Method for preparing chelates of zinc threonine | |
| CN102754739A (en) | Preparation method of composite peptide-copper chelate by utilizing meat processing byproduct | |
| CN101744139A (en) | Fattening cattle full nutrition feed | |
| CN101941938A (en) | Tryptophan chelate and preparation method and application thereof | |
| CN102948620B (en) | Preparation method of modified methionine hydroxy analog-calcium feed additive | |
| CN102603778A (en) | N-carbamyl-L-glutamic zinc complex and preparation method of N-carbamyl-L-glutamic zinc complex | |
| CN102450400A (en) | Forage for hen laying eggs in spring, and preparation method thereof | |
| CN101289411B (en) | Method for preparing zinc threonine | |
| CN106188200B (en) | The preparation method of sucrose zinc complex | |
| CN102627585A (en) | Carbamyl glycine dipeptide chelated zinc and preparation method thereof | |
| CN102627584A (en) | Carbamyl glycine dipeptide chelated copper and preparation method thereof | |
| CN101623049A (en) | Confection of organic green feed additive and using method | |
| CN108218739B (en) | Butyrylglutamic acid derivative, and composition and application thereof | |
| CN103224546A (en) | Hydration amino formyl glycine dipeptide chelating iron and preparation method thereof | |
| CN111072508A (en) | Preparation method and application of zinc valine | |
| CN102894191A (en) | Nutritive feed for supplying vitamins, amino acids and oligosaccharides for pigs | |
| CN102669441A (en) | Spring laying hen edible feed and preparation method thereof | |
| CN105254683A (en) | Alpha-type xylooligosaccharide and preparation method and applications thereof | |
| CN111132962A (en) | Tryptophan derivative and application thereof | |
| CN109221820A (en) | A kind of auxiliary feeding hybridized prussian carp expanded pellet diet of intensive culture mullet and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20120808 |