CN102627585A - Carbamyl glycine dipeptide chelated zinc and preparation method thereof - Google Patents
Carbamyl glycine dipeptide chelated zinc and preparation method thereof Download PDFInfo
- Publication number
- CN102627585A CN102627585A CN2012100818459A CN201210081845A CN102627585A CN 102627585 A CN102627585 A CN 102627585A CN 2012100818459 A CN2012100818459 A CN 2012100818459A CN 201210081845 A CN201210081845 A CN 201210081845A CN 102627585 A CN102627585 A CN 102627585A
- Authority
- CN
- China
- Prior art keywords
- zinc
- carbamoylglycine
- dipeptides
- preparation
- chelating
- 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
Landscapes
- Fodder In General (AREA)
- Peptides Or Proteins (AREA)
Abstract
The invention discloses a novel dipeptide chelate carbamyl glycine dipeptide chelated zinc, with a molecular formula of C6H10N4O6Zn and a structural formula shown as (I). The carbamyl glycine dipeptide chelated zinc shows high absorption rate and high absorption strength in animals, can be used as animal feed additives to supplement zinc element in dietary and improve the growth performance and immunization function of animals; besides, bioavailability of zinc is increased, so as to substantially save mineral resource and reduce environmental stress. The invention also provides a preparation method of the carbamoyl glycine dipeptide chelated zinc. 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 new peptide chelate complexes: carbamoylglycine dipeptides chelating zinc and preparation method thereof.
Background technology
Zinc is one of animal body trace elements necessary, is the moity of multiple metalloenzyme and Regular Insulin.Biochemical functions is called as " bioelement " because of having widely in vivo for it, but can play very important effect to the generation of the sexual development of body, sexual function, sexual cell.Experimentation on animals confirms that scarce zinc can influence the normal growth of animal and cause brain development bad, is embodied in poor growth, and food consumption reduces, apocleisis, and different food is sick, become thin, maldigestion, the sense of taste, baryo,dmia or unusual, degradation under the immunity of organisms.During tradition was raised, the zinc in the animal daily ration was that the form with inorganic salt provides, and the application of adding organic zinc and chelating zinc in recent years is increasingly extensive.Relative inorganic zinc, the organic zinc complex compound receives the protection of ligand, is not vulnerable to the influence that is unfavorable for the physical chemical factor that metal absorbs in the gi tract, has good chemicalstability and biochemical stability.
Organic zinc commonly used is a zinc-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 zinc-amino acid chelate.Thereby, research and develop that a kind of uptake rate is higher, the better organic zinc 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 new dipeptides chelating zn cpds: carbamoylglycine dipeptides chelating zinc.
Another object of the present invention provides the preparation method of above-mentioned carbamoylglycine dipeptides chelating zinc.
Another object of the present invention provides the application of carbamoylglycine dipeptides chelating zinc as fodder additives.
The technical scheme that the present invention adopted is:
Carbamoylglycine dipeptides chelating zinc, its molecular formula is C
6H
10N
4O
6Zn, structural formula is shown in (I):
The preparation method of carbamoylglycine dipeptides chelating zinc comprises the steps:
1) carbamoylglycine is added in the reactor drum, be dissolved in water;
2) add sodium hydroxide, heating for dissolving;
3) continue to add zinc sulfate, 70 ~ 90 ℃ were reacted 2 ~ 4 hours;
4) filter, filter cake obtains carbamoylglycine dipeptides chelating zinc after washing, oven dry.
Preferably, carbamoylglycine: sodium hydroxide: the mol ratio of zinc sulfate is 2 ~ 8:2 ~ 8:1 ~ 4.
Preferably, carbamoylglycine: sodium hydroxide: the mol ratio of zinc sulfate is 2:2:1.
Preferably, in the step 1), the mass volume ratio of carbamoylglycine and water is 1g:1 ~ 2ml.
Carbamoylglycine dipeptides chelating zinc of the present invention can be used as animal feedstuff additive, improves the growth performance and the immune performance of animal body.
Synthetic route of the present invention is following:
Carbamoylglycine dipeptides chelating zinc of the present invention is higher than the uptake rate of zinc-amino acid chelate, and absorption intensity is big, can be used as animal feedstuff additive, replenishes the zinc element in the daily ration, improves the growth performance and the immune performance of animal body.Preparing method's technology of the present invention is simple, and raw material is easy to get, and cost is low, and product purity is higher, steady quality, and technology is convenient to suitability for industrialized production.
Description of drawings
Fig. 1 is the infrared spectrogram of carbamoylglycine dipeptides chelating zinc;
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 1 of carbamoylglycine dipeptides chelating zinc, its concrete steps are following:
Take by weighing 23.6g (0.2mol) carbamoylglycine, add water 40ml, sodium hydroxide 8.0g (0.2mol) is after the heating for dissolving; Add 28.7g (0.1mol) Zinc Sulphate Heptahydrate again, controlled temperature produces a large amount of white precipitates, suction filtration 70 ℃ of reactions 2 hours; Filter cake is with the water washing several, and the absolute ethanol washing solid several times is used in the back, and filter cake is dried; Obtain carbamoylglycine dipeptides chelating zinc 28.2g, detecting zinc content is 21.42%, and nitrogen content is 18.47%.
Embodiment 2
The preparation method 2 of carbamoylglycine dipeptides chelating zinc, its concrete steps are following:
Take by weighing 47.2g (0.4mol) carbamoylglycine, add water 80ml, sodium hydroxide 16.0g (0.4mol) is after the heating for dissolving; Add 57.4g (0.2mol) Zinc Sulphate Heptahydrate again, controlled temperature produces a large amount of white precipitates, suction filtration 80 ℃ of reactions 3 hours; Filter cake is with the water washing several, and the absolute ethanol washing solid several times is used in the back, and filter cake is dried; Obtain carbamoylglycine dipeptides chelating zinc 56.5g, detecting zinc content is 21.46%, and nitrogen content is 18.55%.
Embodiment 3
The preparation method 3 of carbamoylglycine dipeptides chelating zinc, its concrete steps are following:
Take by weighing 70.8g (0.6mol) carbamoylglycine, add water 120ml, sodium hydroxide 24.0g (0.6mol) is after the heating for dissolving; Add 86.1g (0.3mol) Zinc Sulphate Heptahydrate again, controlled temperature produces a large amount of white precipitates, suction filtration 90 ℃ of reactions 3 hours; Filter cake is with the water washing several, and the absolute ethanol washing solid several times is used in the back, and filter cake is dried; Obtain carbamoylglycine dipeptides chelating zinc 83.8g, detecting zinc content is 21.33%, and nitrogen content is 18.23%.
Embodiment 4
The preparation method 4 of carbamoylglycine dipeptides chelating zinc, its concrete steps are following:
Take by weighing 94.4g (0.8mol) carbamoylglycine, add water 160ml, sodium hydroxide 64.0g (0.8mol) is after the heating for dissolving; Add 114.8g (0.4mol) Zinc Sulphate Heptahydrate again, controlled temperature produces a large amount of white precipitates, suction filtration 90 ℃ of reactions 4 hours; Filter cake is with the water washing several, and the absolute ethanol washing solid several times is used in the back, and filter cake is dried; Obtain carbamoylglycine dipeptides chelating zinc 113.1g, detecting zinc content is 21.36%, and nitrogen content is 18.35%.
Embodiment 5
The preparation method 5 of carbamoylglycine dipeptides chelating zinc, its concrete steps are following:
Take by weighing 94.4g (0.8mol) carbamoylglycine, add water 94ml, sodium hydroxide 64.0g (0.8mol) is after the heating for dissolving; Add 114.8g (0.4mol) Zinc Sulphate Heptahydrate again, controlled temperature produces a large amount of white precipitates, suction filtration 80 ℃ of reactions 4 hours; Filter cake is with the water washing several, and the absolute ethanol washing solid several times is used in the back, and filter cake is dried; Obtain carbamoylglycine dipeptides chelating zinc 112.5g, detecting zinc content is 21.42%, and nitrogen content is 18.30%.
Embodiment 6
The preparation method 6 of carbamoylglycine dipeptides chelating zinc, its concrete steps are following:
Take by weighing 94.4g (0.8mol) carbamoylglycine, add water 188ml, sodium hydroxide 64.0g (0.8mol) is after the heating for dissolving; Add 64.4g (0.4mol) zinc sulfate again, controlled temperature produces a large amount of white precipitates, suction filtration 80 ℃ of reactions 3 hours; Filter cake is with the water washing several, and the absolute ethanol washing solid several times is used in the back, and filter cake is dried; Obtain carbamoylglycine dipeptides chelating zinc 113.3g, detecting zinc content is 21.28%, and nitrogen content is 18.38%.
The product that embodiment 1 obtains is used absolute ethanol washing, and oven dry can get the higher carbamoylglycine dipeptides chelating zinc of purity, and molecular formula is C
6H
10N
4O
6Zn is white 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 dipeptides chelating zinc sample presentation carries out ultimate analysis, and Zn, C, H, N content are respectively 21.67%, 23.92%, 2.72%, 18.77% (calculated value: Zn21.84%, C24.05%, H2.69%, N18.71%).Embodiment 2 ~ 6 products obtained therefroms all obtain white powder after same treatment, soluble in water, are insoluble to ethanol, methyl alcohol, acetone and other organic solvent, and sample presentation detects, and the gained infrared spectrogram is extremely similar with Fig. 1, is characterized by same compound.The content of Zn, C, H, N is near calculated value.
Experimentation on animals
Carry out experimentation on animals with embodiment 1 resulting carbamoylglycine dipeptides chelating zinc below.
Will be even with a collection of 400 sizes; Athletic 160 age in days Luo Man hens are raised a week in advance; Therefrom select out product age in days 360 healthy hens identical, that body weight is close and be divided into 6 groups at random, 4 experimental group (being respectively that basal diet adds 20ppm, 40ppm, 60ppm, 80ppm carbamoylglycine dipeptides chelating zinc), a negative control group (basal diet); A positive control group (basal diet adds the 80ppm zinc glycinate), every group of 60 chickens.
This experiment is carried out in the semi open model hen house, and trial period was 6 weeks.Duration of test is fed powder, free choice feeding drinking-water; Keep illumination in 16 hours every day, temperature is at 20-28 ℃, and humidity is at 60-70%.The crude protein content of basal diet is 16.5%, and metabolizable energy is 2750 Kcal/kg, and calcium contents is 3.5%, and phosphorus content is 0.62%.
Performance test: every day time recording each repeat egg number and egg size; Measure each weekly and repeat feed consumption rate and laying hen individual weight; Add up egg size, laying rate, feed consumption rate and feedstuff-egg ratio weekly.
Egg product matter is measured: each repeats to randomly draw 5 pieces of eggs and measures egg shape index and shell thickness weekly.
Slaughter determining: randomly draw 9 hens and butcher, carotid artery is got the hematometry zinc concentration, the quantity of residual zinc in zinc concentration and the ight soil in the shin bone ash content.
Experimental result shows; All experimental group death rates that add carbamoylglycine dipeptides chelating zinc all are lower than positive and negative control group; Wherein negative control group death rate the highest (P < 0.05); It is maximum to have reached on the treatment group numeral that 3.8%. added 40ppm egg number, but with positive control group difference not significantly (P>0.05).The zinc glycinate that adds 80ppm is compared in this explanation, and the carbamoylglycine dipeptides chelating zinc that adds 40ppm not only can reach same effect, and has improved the bioavailability of zinc, can practice thrift Mineral resources greatly, alleviates environmental stress.In experimental group, the laying hen individual weight of negative control group the lightest (P < 0.05), egg productivity is few, and egg shape index is poorer than other experimental group, and broken egg number is maximum.Positive control group and each treatment group difference not remarkable (P>0.05) on the feedstuff-meat ratio, but all with negative control group significant difference (P < 0.05).Zinc concentration can be found out from blood plasma, and the treatment group of 80ppm is the highest, and taking second place is the treatment group and positive control group of 60ppm; Zinc concentration is minimum in the negative control group blood.The quantity of residual zinc is opposite in the similar and ight soil of this deposition situation of zinc from the shin bone ash content.
More than experiment shows, in animal body, carbamoylglycine dipeptides chelating zinc is higher than the uptake rate of zinc-amino acid chelate, and absorption intensity is big, can be used as animal feedstuff additive, replenishes the zinc element in the daily ration, improves the growth performance and the immune performance of animal body.
Claims (6)
1. carbamoylglycine dipeptides chelating zinc, its molecular formula is C
6H
10N
4O
6Zn, structural formula is shown in (I):
2. the preparation method of carbamoylglycine dipeptides chelating zinc comprises the steps:
1) carbamoylglycine is added in the reactor drum, be dissolved in water;
2) add sodium hydroxide, heating for dissolving;
3) continue to add zinc sulfate, 70 ~ 90 ℃ were reacted 2 ~ 4 hours;
4) filter, filter cake obtains carbamoylglycine dipeptides chelating zinc after washing, oven dry.
3. preparation method according to claim 2 is characterized in that carbamoylglycine: sodium hydroxide: the mol ratio of zinc sulfate is 2 ~ 8:2 ~ 8:1 ~ 4.
4. preparation method according to claim 2 is characterized in that carbamoylglycine: sodium hydroxide: the mol ratio of zinc sulfate is 2:2:1.
5. preparation method according to claim 2 is characterized in that, in the step 1), the mass volume ratio of carbamoylglycine and water is 1g:1 ~ 2ml.
6. carbamoylglycine dipeptides chelating zinc is as the application of fodder additives.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012100818459A CN102627585A (en) | 2012-03-26 | 2012-03-26 | Carbamyl glycine dipeptide chelated zinc and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012100818459A CN102627585A (en) | 2012-03-26 | 2012-03-26 | Carbamyl glycine dipeptide chelated zinc and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102627585A true CN102627585A (en) | 2012-08-08 |
Family
ID=46586011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2012100818459A Pending CN102627585A (en) | 2012-03-26 | 2012-03-26 | Carbamyl glycine dipeptide chelated zinc and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102627585A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102942506A (en) * | 2012-11-16 | 2013-02-27 | 长沙道勤生物科技有限公司 | Preparation method for feed additive of N-carbamyl glutamate chelated zinc |
| CN104096229A (en) * | 2014-07-03 | 2014-10-15 | 中国医学科学院医学生物学研究所 | Glycine zinc adjuvant and vaccine containing glycine zinc adjuvant |
| CN108077609A (en) * | 2018-01-16 | 2018-05-29 | 湖南农业大学 | A kind of ruminant domestic animal mixed feed and its application based on zinc-glycine chelate |
| CN113796461A (en) * | 2021-09-18 | 2021-12-17 | 广州康瑞德饲料科技有限公司 | Self-assembled small peptide chelated zinc feed additive and preparation method thereof |
Citations (5)
| 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 |
| 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 CN2012100818459A patent/CN102627585A/en active Pending
Patent 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 |
| US4830716B1 (en) * | 1986-07-03 | 1999-12-07 | Albion Int | Preparation of pharmaceutical grade amino acid chelates |
| 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 (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102942506A (en) * | 2012-11-16 | 2013-02-27 | 长沙道勤生物科技有限公司 | Preparation method for feed additive of N-carbamyl glutamate chelated zinc |
| CN102942506B (en) * | 2012-11-16 | 2015-04-22 | 长沙道勤生物科技有限公司 | Preparation method for feed additive of N-carbamyl glutamate chelated zinc |
| CN104096229A (en) * | 2014-07-03 | 2014-10-15 | 中国医学科学院医学生物学研究所 | Glycine zinc adjuvant and vaccine containing glycine zinc adjuvant |
| CN104096229B (en) * | 2014-07-03 | 2016-08-24 | 中国医学科学院医学生物学研究所 | Zinc glycinate adjuvant and the vaccine containing zinc glycinate adjuvant |
| CN108077609A (en) * | 2018-01-16 | 2018-05-29 | 湖南农业大学 | A kind of ruminant domestic animal mixed feed and its application based on zinc-glycine chelate |
| CN113796461A (en) * | 2021-09-18 | 2021-12-17 | 广州康瑞德饲料科技有限公司 | Self-assembled small peptide chelated zinc feed additive and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1064371C (en) | Seaweed polysaccharide trace-element complex and its preparation method and usage | |
| CN103224461A (en) | Preparation method of large granule crystal form methionine metal chelate and application thereof | |
| CN102524540B (en) | Saving trace element compound packet as well as preparation method and application thereof | |
| CN101139299B (en) | Method for preparing copper zinc aminoacetic acid complex by ball milling solid state | |
| CN102627585A (en) | Carbamyl glycine dipeptide chelated zinc and preparation method thereof | |
| CN102754739A (en) | Preparation method of composite peptide-copper chelate by utilizing meat processing byproduct | |
| CN103431223A (en) | Pollution-free laying hen feed | |
| CN111072508B (en) | Preparation method and application of zinc valine | |
| CN103989018B (en) | Pheasant is raised with auxotype growth promotion preparation and preparation method thereof | |
| CN101289412B (en) | Method for preparing chelates of zinc threonine | |
| CN102603778A (en) | N-carbamyl-L-glutamic zinc complex and preparation method of N-carbamyl-L-glutamic zinc complex | |
| CN101786961A (en) | Chromium threonine, preparation method and application thereof | |
| CN105076722A (en) | Application of alpha-ketoglutaric acid disodium in preparation of poultry feeds | |
| CN102550830B (en) | Method for applying and preparing gamma-aminobutyric acid complex compound | |
| CN103892099A (en) | High-nutrition duck feed additive | |
| CN101289411B (en) | Method for preparing zinc threonine | |
| CN103892097A (en) | High-nutrition chicken feed additive | |
| CN103224546A (en) | Hydration amino formyl glycine dipeptide chelating iron and preparation method thereof | |
| CN102578386A (en) | Compound glycine multi-mineral product as well as preparation method and application thereof | |
| CN109123101A (en) | The application of a kind of preparation method and niacin manganese of niacin manganese in animal feed | |
| CN101139300A (en) | Method for preparing copper zinc aminoacetic acid complex by grinding solid phase | |
| CN103892093A (en) | High-nutrition goose feed additive | |
| CN103005165A (en) | Preparation method of lactobionic acid microelement complex and application of complex as animal feed additive | |
| CN111087318A (en) | Preparation method of zinc serine and application of zinc serine in field of animal feed | |
| CN102627584A (en) | Carbamyl glycine dipeptide chelated copper 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 |