CN117069795A - Synthesis process of acetyl dipeptide-1 - Google Patents
Synthesis process of acetyl dipeptide-1 Download PDFInfo
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- CN117069795A CN117069795A CN202311005974.4A CN202311005974A CN117069795A CN 117069795 A CN117069795 A CN 117069795A CN 202311005974 A CN202311005974 A CN 202311005974A CN 117069795 A CN117069795 A CN 117069795A
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- acetyl dipeptide
- solvent
- reaction
- dipeptide
- synthesizing
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- GFLJSOROHICWQL-KBPBESRZSA-N (2s)-2-[[(2s)-2-acetamido-3-(4-hydroxyphenyl)propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@@H](NC(=O)C)CC1=CC=C(O)C=C1 GFLJSOROHICWQL-KBPBESRZSA-N 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 29
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 14
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims abstract description 11
- CAHKINHBCWCHCF-JTQLQIEISA-N N-acetyl-L-tyrosine Chemical compound CC(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 CAHKINHBCWCHCF-JTQLQIEISA-N 0.000 claims abstract description 11
- 229960003589 arginine hydrochloride Drugs 0.000 claims abstract description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims abstract description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 claims abstract description 11
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 239000012065 filter cake Substances 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 239000013078 crystal Substances 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 4
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 3
- 230000001276 controlling effect Effects 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000000967 suction filtration Methods 0.000 claims description 2
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims 8
- 239000000047 product Substances 0.000 abstract description 4
- 238000009776 industrial production Methods 0.000 abstract description 2
- 238000005580 one pot reaction Methods 0.000 abstract description 2
- 102000004196 processed proteins & peptides Human genes 0.000 abstract description 2
- 108090000765 processed proteins & peptides Proteins 0.000 abstract description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000001514 detection method Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000012467 final product Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 1
- 108090000932 Calcitonin Gene-Related Peptide Proteins 0.000 description 1
- 102100025588 Calcitonin gene-related peptide 1 Human genes 0.000 description 1
- 102000009025 Endorphins Human genes 0.000 description 1
- 108010049140 Endorphins Proteins 0.000 description 1
- 206010015866 Extravasation Diseases 0.000 description 1
- -1 HOSU Chemical compound 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- 102000003797 Neuropeptides Human genes 0.000 description 1
- 108090000189 Neuropeptides Proteins 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 230000036251 extravasation Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/0606—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
The application relates to a synthesis process of acetyl dipeptide-1, which belongs to the technical field of peptides and is characterized by comprising the following steps: adding Ac-Tyr-OH and HOSU into the solvent, controlling the temperature to be 5-10 ℃, dropwise adding DCC solution, and reacting after the dropwise adding is finished; then adding water, arginine hydrochloride and sodium bicarbonate for reaction; removing the solvent from the reaction product, and crystallizing to obtain acetyl dipeptide-1; the acetyl dipeptide-1 product with the purity of more than 99 percent can be prepared by the one-pot method, the process is simple, and the industrial production is easy.
Description
Technical Field
The application relates to the technical field of peptides, in particular to a synthesis process of acetyl dipeptide-1.
Background
The Acetyl Dipeptide-1 is named as Acetyl Dipeptide-1, and is a substance containing tyrosine and arginine. Acetyl dipeptide-1 is a neuropeptide which stimulates the production of endorphin and releases it around the nerve endings of the skin, reducing the pain and heat sensation, and making the skin comfortable and relaxed. Meanwhile, by inhibiting CGRP and SP media, the phenomena of plasma extravasation and microvascular expansion are controlled, and the phenomena of red blood streak and red swelling are inhibited. By dual regulation of neurotransmitters that stimulate muscle activity, muscles are relaxed, appearance of first wrinkles is prevented, depth and length of fine lines are improved, and dynamic, static and fine lines are smoothed.
At present, no related technology exists in the aspect of the synthesis process of the acetyl dipeptide-1, and the application aims to provide a novel synthesis method of the acetyl dipeptide-1 with simple process.
Disclosure of Invention
The application provides a synthesis process of acetyl dipeptide-1, which has simple process and is easy for industrial production, aiming at the problems existing in the prior art.
The technical scheme for solving the technical problems is as follows: the synthesis process of acetyl dipeptide-1 is characterized by comprising the following steps:
adding Ac-Tyr-OH and HOSU (N-hydroxysuccinimide) into a solvent, controlling the temperature to be 5-10 ℃, dropwise adding a DCC (dicyclohexylcarbodiimide) solution, and carrying out reaction after the dropwise adding is finished;
then adding water, arginine hydrochloride and sodium bicarbonate for reaction;
and removing the solvent from the reaction product, and crystallizing to obtain the acetyl dipeptide-1.
The related materials and the reaction process are as follows:
further, the solvent adopts THF, ethyl acetate, butyl acetate, DMF, acetonitrile, dichloromethane, chloroform or NMP; the solvent in the DCC solution is the reaction solvent of the system.
Further, the reaction of Ac-Tyr-OH, HOSU and DCC solution is carried out at normal temperature.
Further, the reaction after adding water, arginine hydrochloride and sodium bicarbonate is carried out at normal temperature.
Further, the solvent is removed from the reaction product by concentrating, preferably by heating.
Further, the crystallization process is as follows:
and (3) regulating the pH value of the reaction product from which the solvent is removed to 1.8-2.2, extracting by adopting an organic solvent, cooling the water phase to 0-5 ℃, regulating the pH value to 4.0-4.4, adding seed crystal acetyl dipeptide-1 for crystallization, and finally carrying out suction filtration, and washing a filter cake to obtain the acetyl dipeptide-1.
Further, the organic solvent used for extraction is ethyl acetate, butyl acetate or tert-butyl acetate.
The beneficial effects of the application are as follows: the application takes Ac-Tyr-OH, HOSU, DCC, arginine hydrochloride and sodium bicarbonate as raw materials, and can prepare the acetyl dipeptide-1 by a one-pot method, the production process is simple, the product yield can reach about 70 percent, and the purity can reach more than 99 percent.
Detailed Description
The principles and features of the present application are described below with examples provided for the purpose of illustration only and are not intended to limit the scope of the application.
Example 1
The synthesis process of the acetyl dipeptide-1 in the embodiment comprises the following steps:
92.4g of DCC was dissolved in 100ml of THF and left at room temperature to prepare a DCC/THF solution.
Into a 2L three-necked flask, 500ml of THF, 100g of Ac-Tyr-OH and 51.6g of HOSU were added, the internal temperature was kept at 5-10℃and the prepared DCC/THF solution was added dropwise, and after completion of the reaction at 25℃for about 2 hours, 600ml of water, 94.4g of arginine hydrochloride and 45.2g of sodium hydrogencarbonate were added. The reaction at an internal temperature of 25 ℃ is carried out, and after TLC detection, no residual raw materials are left, the post-treatment is carried out.
Concentrating at 45 deg.C to remove THF, adjusting pH to 2.0, extracting with ethyl acetate for 3 times (200 ml each time), cooling the water phase to 0-5 deg.C, adjusting pH to 4.3, adding seed crystal acetyl dipeptide-1, vacuum filtering, washing the filter cake with ice water for 3 times (50 ml each time); the filter cake was dried at 55 degrees to give 121.7g of a white solid in 71.6% yield with 99.2% purity.
Example 2
The synthesis process of the acetyl dipeptide-1 in the embodiment comprises the following steps:
92.4g of DCC was dissolved in 100ml of ethyl acetate and left at room temperature to prepare a DCC/ethyl acetate solution.
Into a 2L three-necked flask, 500ml of ethyl acetate, 100g of Ac-Tyr-OH and 51.6g of HOSU were added, the internal temperature was kept at 5-10℃and the prepared DCC/ethyl acetate solution was added dropwise, and after completion of the reaction at 25℃for about 2 hours, 600ml of water, 94.4g of arginine hydrochloride and 45.2g of sodium hydrogencarbonate were added. The reaction at an internal temperature of 25 ℃ is carried out, and after TLC detection, no residual raw materials are left, the post-treatment is carried out.
Concentrating at 45 deg.C to remove solvent, adjusting pH to 2.0, extracting with butyl acetate for 3 times (200 ml each time), cooling the water phase to 0-5 deg.C, adjusting pH to 4.3, adding seed crystal acetyl dipeptide-1, vacuum filtering, washing the filter cake with ice water for 3 times (50 ml each time); the filter cake was dried at 55 degrees to give 119.8g of a white solid in 70.5% yield and 99.1% purity.
Example 3
The synthesis process of the acetyl dipeptide-1 in the embodiment comprises the following steps:
92.4g of DCC was dissolved in 100ml of DMF and left at room temperature to prepare a DCC/DMF solution.
Into a 2L three-necked flask, 500ml of DMF, 100g of Ac-Tyr-OH and 51.6g of HOSU were added, the internal temperature was kept at 5-10℃and the prepared DCC/DMF solution was added dropwise, and after completion of the reaction at 25℃for about 2 hours, 600ml of water, 94.4g of arginine hydrochloride and 45.2g of sodium hydrogencarbonate were added. The reaction at an internal temperature of 25 ℃ is carried out, and after TLC detection, no residual raw materials are left, the post-treatment is carried out.
Concentrating at 45 deg.C to remove solvent, adjusting pH to 2.0, extracting with dichloromethane for 3 times (200 ml each time), cooling the water phase to 0-5 deg.C, adjusting pH to 4.3, adding seed crystal acetyl dipeptide-1, vacuum filtering, washing the filter cake with ice water for 3 times (50 ml each time); the filter cake was dried at 55 degrees to give 118.1g of a white solid. The yield thereof was found to be 69.5% and the purity thereof was found to be 98.7%.
Comparative example 1
The synthesis process of this comparative example was essentially the same as in example 1, except that the extraction solvent ethyl acetate was replaced with dichloromethane. The final product quality was 90.4g, the product yield was 53.2% and the purity was 97.8%.
Comparative example 2
The synthesis process of this comparative example was essentially the same as in example 1, except that the extraction solvent ethyl acetate was replaced with methyl tertiary ether. The final product quality is 76.5g, the product yield is 45% and the purity is 95.4%.
Comparative example 3
184.8g of DCC was dissolved in 200ml of DMF and left at room temperature to prepare a DCC/DMF solution.
1000ml of DMF, 200g of Ac-Tyr-OH and 103.2g of HOSU are added into a 5L three-necked flask, the internal temperature is kept at 5-10 ℃, the prepared DCC/DMF solution is dripped, and after the dripping is completed, the internal temperature is reacted for about 2 hours at 25 ℃, 1200ml of water, 188.8g of arginine hydrochloride and 90.4g of sodium bicarbonate are added. The reaction at an internal temperature of 25 ℃ is carried out, and after TLC detection, no residual raw materials are left, the post-treatment is carried out.
Concentrating at 45 deg.C to remove solvent, adjusting pH to 2.0, extracting with ethyl acetate for 3 times (400 ml each time), cooling the water phase to 0-5 deg.C, adjusting pH to 3.8, adding seed crystal acetyl dipeptide-1, vacuum filtering, washing the filter cake with ice water for 3 times (100 ml each time); the filter cake was dried at 55 degrees to give 222g of a white solid. The yield thereof was found to be 65.3% and the purity thereof was found to be 97.7%.
Comparative example 4
184.8g of DCC was dissolved in 200ml of DMF and left at room temperature to prepare a DCC/DMF solution.
1000ml of DMF, 200g of Ac-Tyr-OH and 103.2g of HOSU are added into a 5L three-necked flask, the internal temperature is kept at 5-10 ℃, the prepared DCC/DMF solution is dripped, and after the dripping is completed, the internal temperature is reacted for about 2 hours at 25 ℃, 1200ml of water, 188.8g of arginine hydrochloride and 90.4g of sodium bicarbonate are added. The reaction at an internal temperature of 25 ℃ is carried out, and after TLC detection, no residual raw materials are left, the post-treatment is carried out.
Concentrating at 45 deg.C to remove solvent, adjusting pH to 2.0, extracting with ethyl acetate for 3 times (400 ml each time), cooling the water phase to 0-5 deg.C, adjusting pH to 4.5, adding seed crystal acetyl dipeptide-1, vacuum filtering, washing the filter cake with ice water for 3 times (100 ml each time); the filter cake was dried at 55 degrees to give 214.8g of a white solid. The yield thereof was found to be 63.2% and the purity thereof was found to be 97.3%.
Claims (10)
1. The synthesis process of acetyl dipeptide-1 is characterized by comprising the following steps:
adding Ac-Tyr-OH and HOSU into the solvent, controlling the temperature to be 5-10 ℃, dropwise adding DCC solution, and reacting after the dropwise adding is finished;
then adding water, arginine hydrochloride and sodium bicarbonate for reaction;
and removing the solvent from the reaction product, and crystallizing to obtain the acetyl dipeptide-1.
2. The process for synthesizing acetyl dipeptide-1 according to claim 1, wherein the solvent is THF, ethyl acetate, butyl acetate, DMF, acetonitrile, dichloromethane, chloroform or NMP.
3. The process for synthesizing acetyl dipeptide-1 according to claim 1 or 2, wherein the solvent in DCC solution is THF, ethyl acetate, butyl acetate, DMF, acetonitrile, dichloromethane, chloroform or NMP.
4. The process for synthesizing acetyl dipeptide-1 according to claim 1 or 2, wherein the reaction of Ac-Tyr-OH, HOSU and DCC solution is carried out at room temperature.
5. The process for synthesizing acetyl dipeptide-1 according to claim 1 or 2, wherein the reaction after adding water, arginine hydrochloride and sodium bicarbonate is carried out at room temperature.
6. The process for the synthesis of acetyl dipeptide-1 according to claim 1 or 2, wherein the solvent removal of the reaction product is performed by concentration.
7. The process for synthesizing acetyl dipeptide-1 according to claim 6, wherein the reaction product is concentrated by heating to remove the solvent.
8. The process for synthesizing acetyl dipeptide-1 according to claim 1, wherein the crystallization process is:
and (3) regulating the pH value of the reaction product from which the solvent is removed to 1.8-2.2, extracting by adopting an organic solvent, cooling the water phase to 0-5 ℃, regulating the pH value to 4.0-4.4, adding seed crystals for crystallization, and finally carrying out suction filtration, and washing a filter cake to obtain the acetyl dipeptide-1.
9. The process for synthesizing acetyl dipeptide-1 according to claim 8, wherein the organic solvent used for extraction is ethyl acetate, butyl acetate or tert-butyl acetate.
10. The process for synthesizing acetyl dipeptide-1 according to claim 8, wherein the seed crystal is acetyl dipeptide-1.
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| CN202311005974.4A CN117069795A (en) | 2023-08-10 | 2023-08-10 | Synthesis process of acetyl dipeptide-1 |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202311005974.4A CN117069795A (en) | 2023-08-10 | 2023-08-10 | Synthesis process of acetyl dipeptide-1 |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0311057A2 (en) * | 1987-10-07 | 1989-04-12 | Ajinomoto Co., Inc. | Process for the production of glutamine derivatives |
| CN105713073A (en) * | 2016-03-31 | 2016-06-29 | 济南康和医药科技有限公司 | Method for liquid phase preparation of atosiban |
| CN107629111A (en) * | 2017-10-26 | 2018-01-26 | 陕西慧康生物科技有限责任公司 | A kind of liquid-phase synthesis process of acetyl group tetrapeptide 2 |
| CN113121673A (en) * | 2021-04-08 | 2021-07-16 | 润辉生物技术（威海）有限公司 | Method for preparing elcatonin by solid-liquid combination method |
| CN113150066A (en) * | 2021-05-06 | 2021-07-23 | 山东济肽生物科技有限公司 | Synthetic method of blue copper peptide |
| CN113845586A (en) * | 2021-11-14 | 2021-12-28 | 汉肽生物医药集团有限公司 | Method for liquid-phase synthesis of acetyl hexapeptide-8 |
-
2023
- 2023-08-10 CN CN202311005974.4A patent/CN117069795A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0311057A2 (en) * | 1987-10-07 | 1989-04-12 | Ajinomoto Co., Inc. | Process for the production of glutamine derivatives |
| CN105713073A (en) * | 2016-03-31 | 2016-06-29 | 济南康和医药科技有限公司 | Method for liquid phase preparation of atosiban |
| CN107629111A (en) * | 2017-10-26 | 2018-01-26 | 陕西慧康生物科技有限责任公司 | A kind of liquid-phase synthesis process of acetyl group tetrapeptide 2 |
| CN113121673A (en) * | 2021-04-08 | 2021-07-16 | 润辉生物技术（威海）有限公司 | Method for preparing elcatonin by solid-liquid combination method |
| CN113150066A (en) * | 2021-05-06 | 2021-07-23 | 山东济肽生物科技有限公司 | Synthetic method of blue copper peptide |
| CN113845586A (en) * | 2021-11-14 | 2021-12-28 | 汉肽生物医药集团有限公司 | Method for liquid-phase synthesis of acetyl hexapeptide-8 |
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| Title |
|---|
| FERNANDO ALBERICIO等: "New treads in peptide coupling reagents", ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, vol. 33, no. 3, 30 June 2001 (2001-06-30), pages 203 - 313 * |
| KAZUO OKUMURA等: "Total synthesis of a macrocyclic antibiotic, Micrococcin P", BULL. CHEM. SOC. JPN., vol. 72, 31 December 1999 (1999-12-31), pages 1561 - 1569 * |
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