CN104109190A - Method for preparing single polypeptide-Zn (II) complex - Google Patents

Method for preparing single polypeptide-Zn (II) complex Download PDF

Info

Publication number
CN104109190A
CN104109190A CN201410326200.6A CN201410326200A CN104109190A CN 104109190 A CN104109190 A CN 104109190A CN 201410326200 A CN201410326200 A CN 201410326200A CN 104109190 A CN104109190 A CN 104109190A
Authority
CN
China
Prior art keywords
polypeptide
title complex
solution
single polypeptide
zine ion
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.)
Granted
Application number
CN201410326200.6A
Other languages
Chinese (zh)
Other versions
CN104109190B (en
Inventor
曾庆祝
许庆陵
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.)
Guangzhou University
Original Assignee
Guangzhou University
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 Guangzhou University filed Critical Guangzhou University
Priority to CN201410326200.6A priority Critical patent/CN104109190B/en
Publication of CN104109190A publication Critical patent/CN104109190A/en
Application granted granted Critical
Publication of CN104109190B publication Critical patent/CN104109190B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Peptides Or Proteins (AREA)

Abstract

The invention discloses a method for preparing, separating and screening single polypeptide and performing oriented synthesis of a polypeptide and trace element zinc complex, namely a single polypeptide-Zn (II) complex. The method comprises the following steps: dissolving, emulsifying, cross-linking, activating, grafting ligand and chelating Zn<2+> to prepare a metal ion affinity medium. The method has not only scientific meaning in theory but also very high practical values.

Description

One is prepared the method for single polypeptide-Zn (II) title complex
Technical field
The screening and the purifying field that the present invention relates to protein polypeptide, specifically one is prepared the method for single polypeptide-Zn (II) title complex.
Background technology
Polypeptide-Zn complex is a kind of novel organometallic compound with composite bio-active function, is polypeptide aglucon and Zn 2+the coordination compound forming by mating reaction.Form wherein a kind of zinc of component of this title complex, as activator and the indispensable component of plurality of enzymes, the requisite trace elements of all biosystems (comprising bacterium, plant, animals and humans), have the title of " bioelement ", it has irreplaceable effect (from acid base equilibrium to immunologic function) to the elementary cell function in all cells system.Body lacks zinc can cause many-sided negative impact, as basal metabolism declines, impact is grown, protein utilization reduction and appetite and digestive function low inferior.According to statistics, there is in the world 17.3% crowd to be in and lack zinc state.Often use at present the zinc supplementation agent of the inorganic zincs such as zinc oxide, zinc sulfate or Zinc Gluconate as human or animal's body.Although metal-salt the most often uses, its bioavailability is in vivo low, and may have side effects.Research is in recent years found, compared with inorganic zinc, the biology utilization ratio that amino acid, polypeptide class and zinc chelating form organic zinc complex is in vivo than the height of inorganic zinc, only need to take in micro-organic zinc and just can reach good zinc supplementation effect, and can avoid inorganic zinc to cause zinc overdose at body internal cause malabsorption, and then produce the harm to human body and environment.At present, about manual method prepare polypeptide and and then the existing pertinent literature report of the research of synthetic polypeptide-Zn complex, it is higher that problem is that manual method is prepared the cost of polypeptide, and the biological activity of polypeptide is lower, even there is no biological activity.From natural product, produce polypeptide and come from natural animal-plant, and activity being higher, is the prior development direction of polypeptide products exploitation.
In the acquired granted patent of applicant (a kind of Zinc-polypeptides complexe and its preparation method and application ZL200810028217.8), set forth proteolysis polypeptide and coordinated the biological function activity and the application thereof that form polypeptide-zinc complex mixture with zinc, be still still open question but how to obtain highly purified polypeptide-Zn complex.
Summary of the invention
Primary and foremost purpose of the present invention is to propose one and prepares, separates, screens single polypeptide, and and then the title complex of a directed synthetic peptide species and trace element zinc be the method for single polypeptide-Zn (II) title complex, existing theoretic scientific meaning, has again very high practical value.The solution of the present invention is as follows for achieving the above object:
One is prepared the method for single polypeptide-Zn (II) title complex:
First metallic zinc ion is fixed on polymer carrier by crosslinked and sequestering action, prepare zine ion affinity column, and by chromatography column, the affinity interaction of protolysate polypeptide is filtered out to zine ion Binding peptide, then adopt eluent that affine polypeptide is eluted, reorientation is synthesized single polypeptide-Zn (II) title complex.
Preferably, described polymer carrier is dextran G-25, chitosan or agarose.
Preferably, preparing zine ion affinity column comprises the following steps:
Dissolve: take polymer carrier, join in the acetic acid solution of mass percent 1%, stir and microwave treatment, until CL, the macromolecular solution of acquisition mass percent 1.5%;
Emulsifying effect: add emulsifying agent in macromolecular solution, water bath with thermostatic control temperature 50-55 DEG C, with the speed continuously stirring 1.0h of 450rpm;
Crosslinked action: the glutaraldehyde of getting mass percent 50% is added drop-wise in above-mentioned solution, then add the NaOH solution of 2mol/L, the speed that continues 450rpm in 50-55 DEG C of water bath with thermostatic control stirs crosslinking reaction 2h, obtains high molecular particle;
Activation: take the high molecular particle after being cross-linked, and mix with epoxy chloropropane (ECH), add again the NaOH solution of 1.2mol/L, put into 50 DEG C, the water bath with thermostatic control vibrator of 130rpm, priming reaction 1.5h, take out with vacuum filtration pump suction filtration, rush and remove NaOH solution with distillation washing;
Access aglucon: take activation particulate, add wherein imino-oxalic acid (IDA) and 1.2mol/L NaOH solution and be positioned in 50 DEG C, 30rpm constant temperature oscillator and react 4h, again mixed solution is carried out to suction filtration, the IDA of microparticle surfaces is cleaned up with deionized water, obtain accessing the high molecular particle of aglucon IDA;
Chelating Zn 2+prepare zine ion affinity media: take the particulate that has connected IDA, add wherein the ZnSO of 0.25mol/L 4solution, the 3h of concussion reaction at normal temperatures, pour mixed solution into Büchner funnel and carry out suction filtration, obtain polymer zine ion affinity chromatography glue with deionized water wash microballoon, by filtrate collection and be diluted to 50000 times, by the zinc ion content in atomic absorption spectroscopy determination filtrate, calculate the amount of chromatography glue chelated zinc ion according to the difference of zinc ion concentration in zinc ion concentration and filtrate before reaction.
Preferably, described emulsifying agent is glycerine or paraffin.
Preferably, filter out zine ion Binding peptide, adopt eluent that affine polypeptide wash-out is comprised the following steps:
The zine ion affinity media of preparation is packed in chromatography column, then the tilapia hydrolysis protein polypeptide liquid of implantation quality per-cent 20% makes it through chromatography column wherein, adopts 0.1mol/L EDTA solution as elutriant, collects the polypeptide fraction of being combined with zine ion.
Preferably, directed synthetic single polypeptide-Zn (II) title complex refers to collects the polypeptide of being combined with zine ion, synthetic polypeptide-Zn (II) title complex.
Preferably, the Zn quality proportioning of polypeptide N and zinc acetate is 4:1, and pH is 4.5, and temperature of reaction is 45 DEG C, and the reaction times is 40min, with this understanding, and polypeptide and Zn 2+there is mating reaction and generate polypeptide-Zn complex.
Prepare specific polypeptide-Zn complex, first must prepare single polypeptide aglucon, be a domestic and international problem that has a difficult point but how to obtain single protein polypeptide always, need to set up special technological method and could realize the preparation of single polypeptide.The method of preparing single polypeptide-Zn (II) title complex provided by the invention has following beneficial effect:
(1) technical parameter prepared by clear and definite zine ion affinity media, set up a kind of zine ion affinity media by preparation screens from the polypeptide mixture of fish-protein hydrolysate, isolate a kind of effective ways that zine ion had to the polypeptide of stronger avidity, and analyze disclosed obtain single polypeptide from N hold to the aminoacid sequence of C end be (being formed by 12 amino acid): Thr-Phe-Pro-Gly-Phe-Gln-Gly-Pro-Val-Gly-Pro-Arg (Threonine-phenylalanine-proline(Pro)-Gly-Phe-glutamine-Gly-Pro-α-amino-isovaleric acid-Gly-Pro-arginine).
(2) method of obtaining the affine polypeptide of single zine ion from hydrolyzed fish protein mixture that adopts this invention to provide, prepares the single polypeptide being made up of 12 amino acid, and and then has synthesized polypeptide-Zn (II) title complex.
(3) adopt this method to obtain single polypeptide-Zn (II) title complex, lay the foundation for further probing into its structure activity relationship and manually designing synthetic such title complex.
Brief description of the drawings
Fig. 1 is embodiment of the present invention preparation technology schema;
Fig. 2 is embodiment of the present invention high molecular particle isolated polypeptide collection of illustrative plates;
Fig. 3 is embodiment of the present invention high molecular particle immobilization zine ion chromatographic separation polypeptide collection of illustrative plates;
Fig. 4 is embodiment of the present invention polypeptide and polypeptide-Zn complex infrared spectrogram.
Embodiment
Object of the present invention realizes the method for a kind of directional preparation polypeptide-Zn (II) title complex by following proposal, preparation technology's flow process as shown in Figure 1:
1, polymer carrier refers to dextran G-25, agarose, chitosan, first-selected dextran G-25.
2, dissolve: take 1.5g polymer carrier, join in the acetic acid solution of mass percent 1%, stir and microwave treatment, until CL, the macromolecular solution of acquisition mass percent 1.5%.
3, emulsifying effect: add 25mL glycerine or paraffin as emulsifying agent in macromolecular solution, water bath with thermostatic control temperature 50-55 DEG C, with the speed continuously stirring 1.0h of 450rpm.
4, crosslinked action: the glutaraldehyde of getting 0.5mL mass percent 50% is added drop-wise in above-mentioned solution, then add the NaOH solution 2mL of 2mol/L, the speed that continues 450rpm in 50-55 DEG C of water bath with thermostatic control stirs crosslinking reaction 2h, obtains high molecular particle.
5, activation: take the high molecular particle after 2g is cross-linked, and mix with 10mL epoxy chloropropane (ECH), add again the NaOH solution of 20mL1.2mol/L, put into the water bath with thermostatic control vibrator of 50 DEG C of 130rpm, priming reaction 1.5h, take out with vacuum filtration pump suction filtration, rush and remove NaOH solution with distillation washing.
6, access aglucon: take activation particulate 2g, add wherein imino-oxalic acid (IDA) and the 20ml1.2mol/L NaOH solution of 1.8g and be positioned in 50 DEG C of 130rpm constant temperature oscillators and react 4h.Again mixed solution is poured into and in Büchner funnel, carried out suction filtration, the IDA of microparticle surfaces is cleaned up with deionized water, obtain accessing the high molecular particle of aglucon IDA.
7, chelating Zn 2+prepare zine ion affinity media: take the particulate that 1.0g has connected IDA, add wherein the ZnSO of 25ml0.25mol/L 4solution, the 3h of concussion reaction at normal temperatures.Pour mixed solution into Büchner funnel and carry out suction filtration, obtain polymer zine ion affinity chromatography glue with deionized water wash microballoon.By filtrate collection and be diluted to 50000 times.By the zinc ion content in atomic absorption spectroscopy determination filtrate, calculate the amount of chromatography glue chelated zinc ion according to the difference of zinc ion concentration in zinc ion concentration and filtrate before reaction.
8, polypeptide chromatography and wash-out: the polymer zine ion affinity media of preparation is packed in chromatography column, then add wherein the tilapia hydrolysis protein polypeptide liquid of 2ml mass percent 20% to make it through chromatography column; Adopt 0.1mol/L EDTA solution as elutriant, under wavelength 280nm, detect polypeptide fraction, the polypeptide fraction (the second peak of wash-out) that collection is combined with zine ion, freeze concentration drying for standby with ultraviolet tomographic map spectra system.Detect collection of illustrative plates as shown in Figure 2 and Figure 3.
9, the purifying of polypeptide and amino acid sequence analysis: the lyophilize polypeptide of above-mentioned preparation passes through RPLC purifying and amino acid sequence analysis again, determines that the amino acid composition of polypeptide is Arg, Gln, Gly 3, Phe 2, Pro 3, Thr, Val, polypeptide from N hold to the aminoacid sequence of C end be Thr-Phe-Pro-Gly-Phe-Gln-Gly-Pro-Val-Gly-Pro-Arg (Threonine-phenylalanine-proline(Pro)-Gly-Phe-glutamine-Gly-Pro-α-amino-isovaleric acid-Gly-Pro-arginine).
10, mating reaction: the Zn quality proportioning of polypeptide N and zinc acetate is 4:1, and pH is 4.5, and temperature of reaction is 45 DEG C, and the reaction times is 40min, with this understanding, polypeptide and Zn 2+there is mating reaction and generate polypeptide-Zn complex.
11, as shown in Figure 4, polypeptide and the structural analysis of polypeptide-Zn complex: can find out from infrared spectrogram, polypeptide is at 3349cm -1there is a wide absorption peak at place, and this is to be caused by the stretching vibration of the N-H of acid amides, and in the absorption band of polypeptide-Zn complex, this spectrum peak moves to compared with lower wave number 3294cm -1place, red shift 54.50cm -1.Polypeptide is at 2959cm -1the absorption peak at place, this is by-CH 3group stretching vibration causes, is converted to 2964cm in polypeptide-Zn complex -1place, blue shift 5.30cm -1, intensity has also weakened, and polypeptide-Zn complex is at 3077cm -1place has occurred Zn being described absorption peak 2+after being combined with polypeptide, there is change in the node configuration of polypeptide.Polypeptide is at 1650cm- 1near have the characteristic spectrum peak of stretching vibration acid amides I band, this is to be caused by the C=O stretching vibration of acid amides.Polypeptide and Zn 2+in conjunction with after, this band position has transformed to 1655cm -1, blue shift 5.30cm -1.Polypeptide is at 1596cm -1there is an absorption peak at place, may be caused by C=N, C=C stretching vibration, with Zn 2+disappear in conjunction with rear this peak.Polypeptide is at polypeptide absorption band 1400cm -1near the characteristic spectrum peak that has stretching vibration acid amides III band place has, this is to be caused by the N-H flexural vibration of acid amides or the stretching vibration of C-N, transforms to 1398cm at the absorption band of polypeptide-Zn complex -1, red shift 2.27cm -1.Then the fingerprint region of observing spectrum, polypeptide is at 1113cm -1and 1048cm -1there is respectively a characteristic peak at place, and this is caused by C-O stretching vibration, but these two spectrum peaks of polypeptide-Zn complex have all disappeared.At polypeptide absorption band 652cm -1there is a wide absorption peak at place near having, and this causes by the outer formation vibration of N-H face, and polypeptide is combined rear this band position and is transformed to 669cm with zinc -1, blue shift 16.65cm -1.These results show Zn above 2+with the cooperation position of polypeptide may be on the Sauerstoffatom of the nitrogen-atoms of N-H and C=O or C-O.
Embodiment recited above is described the preferred embodiment of the present invention, not the spirit and scope of the present invention is limited.Do not departing under the prerequisite of design concept of the present invention; various modification and improvement that this area ordinary person makes technical scheme of the present invention; all should drop into protection scope of the present invention, the technology contents of request protection of the present invention, has all been documented in claims.

Claims (7)

1. a method of preparing single polypeptide-Zn (II) title complex, is characterized in that:
First metallic zinc ion is fixed on polymer carrier by crosslinked and sequestering action, prepare zine ion affinity column, and by chromatography column, the affinity interaction of protolysate polypeptide is filtered out to zine ion Binding peptide, then adopt eluent that affine polypeptide is eluted, reorientation is synthesized single polypeptide-Zn (II) title complex.
2. the method for preparing single polypeptide-Zn (II) title complex as claimed in claim 1, is characterized in that: described polymer carrier is dextran G-25, chitosan or agarose.
3. the method for preparing single polypeptide-Zn (II) title complex as claimed in claim 1, is characterized in that preparing zine ion affinity column and comprises the following steps:
Dissolve: take polymer carrier, join in the acetic acid solution of mass percent 1%, stir and microwave treatment, until CL, the macromolecular solution of acquisition mass percent 1.5%;
Emulsifying effect: add emulsifying agent in macromolecular solution, water bath with thermostatic control temperature 50-55 DEG C, with the speed continuously stirring 1.0h of 450rpm;
Crosslinked action: the glutaraldehyde of getting mass percent 50% is added drop-wise in above-mentioned solution, then add the NaOH solution of 2mol/L, the speed that continues 450rpm in 50-55 DEG C of water bath with thermostatic control stirs crosslinking reaction 2h, obtains high molecular particle;
Activation: take the high molecular particle after being cross-linked, and mix with epoxy chloropropane (ECH), add again the NaOH solution of 1.2mol/L, put into 50 DEG C, the water bath with thermostatic control vibrator of 130rpm, priming reaction 1.5h, take out with vacuum filtration pump suction filtration, rush and remove NaOH solution with distillation washing;
Access aglucon: take activation particulate, add wherein imino-oxalic acid (IDA) and 1.2mol/L NaOH solution and be positioned in 50 DEG C, 30rpm constant temperature oscillator and react 4h, again mixed solution is carried out to suction filtration, the IDA of microparticle surfaces is cleaned up with deionized water, obtain accessing the high molecular particle of aglucon IDA;
Chelating Zn 2+prepare zine ion affinity media: take the particulate that has connected IDA, add wherein the ZnSO of 0.25mol/L 4solution, the 3h of concussion reaction at normal temperatures, pour mixed solution into Büchner funnel and carry out suction filtration, obtain polymer zine ion affinity chromatography glue with deionized water wash microballoon, by filtrate collection and be diluted to 50000 times, by the zinc ion content in atomic absorption spectroscopy determination filtrate, calculate the amount of chromatography glue chelated zinc ion according to the difference of zinc ion concentration in zinc ion concentration and filtrate before reaction.
4. the method for preparing single polypeptide-Zn (II) title complex as claimed in claim 3, is characterized in that: described emulsifying agent is glycerine or paraffin.
5. the method for preparing single polypeptide-Zn (II) title complex as claimed in claim 1, is characterized in that filtering out zine ion Binding peptide, adopts eluent that affine polypeptide wash-out is comprised the following steps:
The zine ion affinity media of preparation is packed in chromatography column, then the tilapia hydrolysis protein polypeptide liquid of implantation quality per-cent 20% makes it through chromatography column wherein, adopts 0.1mol/LEDTA solution as elutriant, collects the polypeptide fraction of being combined with zine ion.
6. the method for preparing single polypeptide-Zn (II) title complex as claimed in claim 1, is characterized in that:
Directed synthetic single polypeptide-Zn (II) title complex refers to collects the polypeptide of being combined with zine ion, synthetic polypeptide-Zn (II) title complex.
7. the method for preparing single polypeptide-Zn (II) title complex as claimed in claim 6, is characterized in that:
The Zn quality proportioning of polypeptide N and zinc acetate is 4:1, and pH is 4.5, and temperature of reaction is 45 DEG C, and the reaction times is 40min, with this understanding, and polypeptide and Zn 2+there is mating reaction and generate polypeptide-Zn complex.
CN201410326200.6A 2014-07-09 2014-07-09 It is a kind of to prepare single polypeptide-Zn(Ⅱ)The method of complex Active CN104109190B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201410326200.6A CN104109190B (en) 2014-07-09 2014-07-09 It is a kind of to prepare single polypeptide-Zn(Ⅱ)The method of complex

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201410326200.6A CN104109190B (en) 2014-07-09 2014-07-09 It is a kind of to prepare single polypeptide-Zn(Ⅱ)The method of complex

Publications (2)

Publication Number Publication Date
CN104109190A true CN104109190A (en) 2014-10-22
CN104109190B CN104109190B (en) 2018-11-09

Family

ID=51706193

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201410326200.6A Active CN104109190B (en) 2014-07-09 2014-07-09 It is a kind of to prepare single polypeptide-Zn(Ⅱ)The method of complex

Country Status (1)

Country Link
CN (1) CN104109190B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107219177A (en) * 2017-05-31 2017-09-29 浙江海洋大学 The method of zinc, copper, total chrome content in METHOD FOR CONTINUOUS DETERMINATION hemipelagic sediment
CN109675535A (en) * 2018-12-18 2019-04-26 杨小丽 Immobilization zinc ion affinity chromatographic material and its preparation method and application
CN114634882A (en) * 2022-03-25 2022-06-17 广州大学 Method for promoting yeast growth and fermentation

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1525165A (en) * 2003-02-25 2004-09-01 上海实业科华生物技术有限公司 Preparation method of metal chelation chromatography stuffing
CN103626847A (en) * 2013-11-15 2014-03-12 江南大学 Wheat germ protein source zinc phytochelatin and preparation method thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1525165A (en) * 2003-02-25 2004-09-01 上海实业科华生物技术有限公司 Preparation method of metal chelation chromatography stuffing
CN103626847A (en) * 2013-11-15 2014-03-12 江南大学 Wheat germ protein source zinc phytochelatin and preparation method thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
SHI Y C,JIANG Y M,SUI D X,ET AL.: "Affinity chromatography of trypsin using chitosan as ligand support", 《JOURNAL OF CHROMATOGRAPHY A》 *
许庆陵: "罗非鱼多肽 - 锌配合物的制备及其生物活性", 《食品科学》 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107219177A (en) * 2017-05-31 2017-09-29 浙江海洋大学 The method of zinc, copper, total chrome content in METHOD FOR CONTINUOUS DETERMINATION hemipelagic sediment
CN109675535A (en) * 2018-12-18 2019-04-26 杨小丽 Immobilization zinc ion affinity chromatographic material and its preparation method and application
CN109675535B (en) * 2018-12-18 2021-10-22 杨小丽 Immobilized zinc ion affinity chromatography material and preparation method and application thereof
CN114634882A (en) * 2022-03-25 2022-06-17 广州大学 Method for promoting yeast growth and fermentation
CN114634882B (en) * 2022-03-25 2023-06-20 广州大学 Method for promoting yeast growth and fermentation

Also Published As

Publication number Publication date
CN104109190B (en) 2018-11-09

Similar Documents

Publication Publication Date Title
CN104710525B (en) Tuna bone collagen source zinc chelated collagen peptide and preparation method and application thereof
CN104109190A (en) Method for preparing single polypeptide-Zn (II) complex
CN102603869B (en) Synthetic method of hexapeptide
CN104117345A (en) Hydrophobic charge-induced chromatography media with difunctional group and preparation method of hydrophobic charge-induced chromatography media with difunctional group
CN101824085B (en) Method for separating alpha s-casein
JP6147340B2 (en) Cleaning composition, protein purification method, and protein
CN103626847A (en) Wheat germ protein source zinc phytochelatin and preparation method thereof
CN102241754A (en) Method for separating and purifying phycoerythrin from bangia fusco-purpurea
CN1865280A (en) Solid phase polypeptide synthesis preparation method for leuprorelin
CN102550824A (en) Method for producing small peptide amino acid microelement chelate by way of acid hydrolysis of protein
RU2013137811A (en) CLEANING INSULIN
CN1907086A (en) Active organic chromium feed addictive preparation method
CN103705539A (en) Preparation method of pig spleen transfer factor
CN103936828A (en) Preparation method of carfilzomib intermediate and carfilzomib
CN104610446A (en) Jerk filefish skin collagen antioxidative peptide and preparation method thereof
CN102775471B (en) Method for synthesizing cholecystokinin octapeptide by combining solid phase method and liquid phase method
CN102960850B (en) The manufacture method of modification extract and the method for reducing tobacco sheets by paper making method heavy metal ion content
CN101230089A (en) Solid-phase synthesis of glycyl histidyl lycine
CN113912673A (en) Low-bitter ACE inhibitory peptide derived from sesame, and preparation method and application thereof
CN1733796A (en) Thymus gland pentapeptide synthesis technique
CN110818771A (en) Carbonyl sulfide mediated polypeptide synthesis using amino acid ionic liquids
CN107876017B (en) Preparation method of hydrophobic charge induction chromatography medium with bifunctional groups
CN101302008B (en) Solid phase synthesis method of single addition fullerene aminoacid derivate
CN103724420B (en) A kind of Swine spleen transfer factor extracting method
CN101906131B (en) Phosphorylation peptide gathering method based on metal hybridization mesoporous material

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
EE01 Entry into force of recordation of patent licensing contract
EE01 Entry into force of recordation of patent licensing contract

Application publication date: 20141022

Assignee: Guangzhou Aimu Cosmetics Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022440000155

Denomination of invention: A method for preparing single polypeptide-Zn(II) complex

Granted publication date: 20181109

License type: Common License

Record date: 20220921

EE01 Entry into force of recordation of patent licensing contract
EE01 Entry into force of recordation of patent licensing contract

Application publication date: 20141022

Assignee: Foshan Junfu Door and Window Technology Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022440000184

Denomination of invention: A Method for Preparing Single Polypeptide Zn (II) Complex

Granted publication date: 20181109

License type: Common License

Record date: 20220926

Application publication date: 20141022

Assignee: Guangzhou Lifan Enterprise Service Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022440000177

Denomination of invention: A Method for Preparing Single Polypeptide Zn (II) Complex

Granted publication date: 20181109

License type: Common License

Record date: 20220923

Application publication date: 20141022

Assignee: Guangzhou fashion bazaar International Biotechnology Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022440000188

Denomination of invention: A Method for Preparing Single Polypeptide Zn (II) Complex

Granted publication date: 20181109

License type: Common License

Record date: 20220926

Application publication date: 20141022

Assignee: GUANGZHOU JINSHI PLASTIC PRODUCTS CO.,LTD.

Assignor: Guangzhou University

Contract record no.: X2022440000187

Denomination of invention: A Method for Preparing Single Polypeptide Zn (II) Complex

Granted publication date: 20181109

License type: Common License

Record date: 20220926

Application publication date: 20141022

Assignee: GUANGZHOU YOUAN GIVIL ENGINEERING TECHNOLOGY Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022440000186

Denomination of invention: A Method for Preparing Single Polypeptide Zn (II) Complex

Granted publication date: 20181109

License type: Common License

Record date: 20220926

Application publication date: 20141022

Assignee: GUANGZHOU JIERUN RUBBER AND PLASTIC CO.,LTD.

Assignor: Guangzhou University

Contract record no.: X2022440000185

Denomination of invention: A Method for Preparing Single Polypeptide Zn (II) Complex

Granted publication date: 20181109

License type: Common License

Record date: 20220926

Application publication date: 20141022

Assignee: Foshan fast Goldman Sachs Packaging Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022440000178

Denomination of invention: A Method for Preparing Single Polypeptide Zn (II) Complex

Granted publication date: 20181109

License type: Common License

Record date: 20220923

Application publication date: 20141022

Assignee: Guangzhou Lize Cosmetics Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022440000183

Denomination of invention: A Method for Preparing Single Polypeptide Zn (II) Complex

Granted publication date: 20181109

License type: Common License

Record date: 20220926

Application publication date: 20141022

Assignee: Inspiration (Guangzhou) Food Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022440000182

Denomination of invention: A Method for Preparing Single Polypeptide Zn (II) Complex

Granted publication date: 20181109

License type: Common License

Record date: 20220926

Application publication date: 20141022

Assignee: Shenzhen Dingtian Steel Structure Engineering Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022440000181

Denomination of invention: A Method for Preparing Single Polypeptide Zn (II) Complex

Granted publication date: 20181109

License type: Common License

Record date: 20220926

Application publication date: 20141022

Assignee: Guangzhou anzhuo Sealing Technology Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022440000180

Denomination of invention: A Method for Preparing Single Polypeptide Zn (II) Complex

Granted publication date: 20181109

License type: Common License

Record date: 20220926

Application publication date: 20141022

Assignee: Guangzhou Huarui Wenchuang Technology Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022440000179

Denomination of invention: A Method for Preparing Single Polypeptide Zn (II) Complex

Granted publication date: 20181109

License type: Common License

Record date: 20220926

EE01 Entry into force of recordation of patent licensing contract
EE01 Entry into force of recordation of patent licensing contract

Application publication date: 20141022

Assignee: GUANGZHOU YINGKE CHEMICAL TECHNOLOGY Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022980021672

Denomination of invention: A Method for Preparing Single Polypeptide Zn (II) Complex

Granted publication date: 20181109

License type: Common License

Record date: 20221114

EE01 Entry into force of recordation of patent licensing contract
EE01 Entry into force of recordation of patent licensing contract

Application publication date: 20141022

Assignee: Guangdong Xinjing Traditional Chinese Medicine Development Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022980027251

Denomination of invention: A Method for Preparation of Single Peptide Zn (II) Complexes

Granted publication date: 20181109

License type: Common License

Record date: 20230103

EE01 Entry into force of recordation of patent licensing contract
EE01 Entry into force of recordation of patent licensing contract

Application publication date: 20141022

Assignee: Guangdong Zhongyao Pharmaceutical Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022980028709

Denomination of invention: A Method for Preparation of Single Peptide Zn (II) Complexes

Granted publication date: 20181109

License type: Common License

Record date: 20230105

Application publication date: 20141022

Assignee: Guangzhou Zhengsheng teaching equipment Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022980028530

Denomination of invention: A Method for Preparation of Single Peptide Zn (II) Complexes

Granted publication date: 20181109

License type: Common License

Record date: 20230105

Application publication date: 20141022

Assignee: Dongguan Xuanpin Mold Technology Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022980028563

Denomination of invention: A Method for Preparation of Single Peptide Zn (II) Complexes

Granted publication date: 20181109

License type: Common License

Record date: 20230105

Application publication date: 20141022

Assignee: CIDA (Guangzhou) Biotechnology Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022980028405

Denomination of invention: A Method for Preparation of Single Peptide Zn (II) Complexes

Granted publication date: 20181109

License type: Common License

Record date: 20230105

Application publication date: 20141022

Assignee: GUANGZHOU RUIHAO ENVIRONMENTAL TECHNOLOGY CO.,LTD.

Assignor: Guangzhou University

Contract record no.: X2022980028030

Denomination of invention: A Method for Preparation of Single Peptide Zn (II) Complexes

Granted publication date: 20181109

License type: Common License

Record date: 20230105

Application publication date: 20141022

Assignee: Guangzhou Jinhai YOUPIN Biotechnology Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022980028424

Denomination of invention: A Method for Preparation of Single Peptide Zn (II) Complexes

Granted publication date: 20181109

License type: Common License

Record date: 20230105

Application publication date: 20141022

Assignee: Zhongbo Medical Supplies (Guangdong) Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022980028416

Denomination of invention: A Method for Preparation of Single Peptide Zn (II) Complexes

Granted publication date: 20181109

License type: Common License

Record date: 20230106

EE01 Entry into force of recordation of patent licensing contract
EE01 Entry into force of recordation of patent licensing contract

Application publication date: 20141022

Assignee: Guangzhou aozhide Chemical Technology Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2022980028050

Denomination of invention: A Method for Preparation of Single Peptide Zn (II) Complexes

Granted publication date: 20181109

License type: Common License

Record date: 20230110

EE01 Entry into force of recordation of patent licensing contract
EE01 Entry into force of recordation of patent licensing contract

Application publication date: 20141022

Assignee: Foshan Maiding Heat Resistant Material Co.,Ltd.

Assignor: Guangzhou University

Contract record no.: X2023980031825

Denomination of invention: A Method for Preparation of Single Peptide Zn (II) Complexes

Granted publication date: 20181109

License type: Common License

Record date: 20230208