CN111004306A - Liquid phase synthesis method of palmitoyl tripeptide-5 - Google Patents
Liquid phase synthesis method of palmitoyl tripeptide-5 Download PDFInfo
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Abstract
The invention discloses a liquid-phase synthesis method of palmitoyl tripeptide-5, belonging to the technical field of biological medicine preparation methods and comprising the following steps: Pal-Lys (Boc) -OH synthesis, Pal-Lys (Boc) -OSu synthesis, Val-NCA synthesis, H-Val-Lys (Boc) -OH synthesis, Pal-Lys (Boc) Val-Lys (Boc) -OH synthesis, palmitoyl tripeptide-5 synthesis, and the product is dried in vacuum to obtain a white solid. According to the liquid phase synthesis method of palmitoyl tripeptide-5, the final product can be purified by a crystallization method, so that the final liquid phase purification required in solid phase synthesis is successfully avoided, the production cost is reduced, and the batch production capacity is increased.
Description
Technical Field
The invention belongs to the technical field of biological medicine preparation methods, and particularly relates to a liquid-phase synthesis method of palmitoyl tripeptide-5.
Background
Anti-aging palmitoyl tripeptide-5 (sequence: Pal-KVK) is a product of DSM, under the trade name SYN-COLL, a palmitoyl tripeptide, the sequence of which is similar to the mechanism of the human body itself, and collagen is produced by activating latent non-bioactive TGF- β (tissue growth factor). therefore, it can be used as a supplement to skin collagen deficiency to make skin younger, and can reduce any type of wrinkles.
The synthesis of the product is not reported in documents, and the product is synthesized by adopting a solid-phase synthesis method and purifying a preparation liquid phase after resin cutting, so that the cost is high and the pollution to the environment is large.
Disclosure of Invention
The invention aims to provide a liquid phase synthesis method of palmitoyl tripeptide-5, so as to solve the problems.
In order to achieve the purpose, the invention adopts the technical scheme that:
the liquid phase synthesis method of palmitoyl tripeptide-5 comprises the following steps:
1) synthesis of Pal-Lys (Boc) -OH:
adding water and NE- (tert-butoxycarbonyl) -L-lysine into a reaction device in sequence under stirring, adjusting the pH to 10 by using a 30% sodium hydroxide solution, controlling the pH to 10 by using a 30% sodium hydroxide solution while dropwise adding palmitoyl chloride, completely controlling the pH to 10, reacting at room temperature, adjusting the pH to 2 to precipitate a large amount of solid, filtering, and drying the solid in vacuum;
2) synthesis of Pal-Lys (Boc) -OSu:
sequentially adding tetrahydrofuran in a reaction device under stirring, sequentially adding Pal-Lys (Boc) -OH obtained in the step 1), cooling to 0-5 ℃, adding N-hydroxysuccinimide, stirring for 10min, adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride in batches, reacting at room temperature, filtering, concentrating under reduced pressure to obtain a white solid, pulping a filter cake with isopropanol, filtering, and drying the solid in vacuum;
3) Val-NCA Synthesis:
adding tetrahydrofuran, valine and triphosgene into a reaction device in turn under stirring, reacting for 2h at 50 ℃, concentrating under reduced pressure, adding petroleum ether after concentrating, pulping, filtering, and drying the solid in vacuum;
4) synthesis of H-Val-Lys (Boc) -OH:
adding water, tetrahydrofuran, sodium hydroxide and NE- (tert-butoxycarbonyl) -L-lysine into a reaction device in sequence under stirring, cooling by a cold trap, adding Val-NCA obtained in the step 3) while controlling the pH to be 11 by using a 30% sodium hydroxide solution, heating for reaction for 1-2h after dropwise addition, adjusting the pH to be 2, extracting by using n-butanol, washing by using brine, drying by using anhydrous magnesium sulfate, and concentrating under reduced pressure to obtain an oily substance;
5) synthesis of Pal-Lys (Boc) Val-Lys (Boc) -OH:
adding water, tetrahydrofuran, Pal-Lys-OSu obtained in the step 2) and H-Val-Lys (boc) -OH obtained in the step 4) into a reaction device, adjusting the pH to 8.5 with a 30% sodium hydroxide solution, reacting at room temperature for 2 hours, concentrating under reduced pressure, adjusting the pH to 2, extracting with ethyl acetate, washing with brine, and concentrating under reduced pressure to obtain a white solid;
6) synthesis of palmitoyl tripeptide-5:
and (3) sequentially adding trifluoroacetic acid and the Pal-Lys (Boc) -Val-Lys (Boc) -OH obtained in the step 5) into a reaction device under stirring, reacting for 2h at room temperature, dripping the material liquid into a crystallization reagent, filtering to obtain a qualified product, and drying the product in vacuum to obtain a white solid.
The reaction time in the step 1) is controlled to be 2-3 hours.
In the step 2), the reaction time is controlled to be 14-16 hours at room temperature.
And 4) cooling the cold trap to 0-5 ℃, and heating to 25 +/-2 ℃ after the dropwise addition.
In steps 1), 4) and 5), 6M hydrochloric acid was used to adjust pH 2.
The crystallization reagent adopted in the step 6) is ethyl acetate.
The invention has the beneficial effects that: according to the liquid phase synthesis method of palmitoyl tripeptide-5, the final product can be purified by a crystallization method, so that the final liquid phase purification required in solid phase synthesis is successfully avoided, the production cost is reduced, and the batch production capacity is increased.
Detailed Description
Example 1
The liquid phase synthesis method of palmitoyl tripeptide-5 comprises the following steps:
1) synthesis of Pal-Lys (Boc) -OH
In a 500ml three-necked flask equipped with a thermometer and a stirrer, 200ml of water, 21.51g (87.31mmol) of NE- (tert-butoxycarbonyl) -L-lysine, was added under stirring, the pH was adjusted to 10 with a 30% sodium hydroxide solution, 20g (72.76mmol) of palmitoyl chloride was added dropwise under stirring, the pH was adjusted to 10 with a 30% sodium hydroxide solution, the reaction was completed at room temperature for 2 hours, a large amount of solid was precipitated by adjusting the pH to 2 with 6M hydrochloric acid, the resulting solution was filtered, and the cake was vacuum-dried to obtain 33.61g of a white solid with a molar yield of 95.3%;
2) synthesis of Pal-Lys (Boc) -OSu in a 250ml three-necked flask equipped with a thermometer and a stirrer, 60ml of tetrahydrofuran and 4.75g (24.76mmol) of 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride are added in portions into a 250ml three-necked flask with a stirrer under stirring, the temperature is reduced to 0-5 ℃, 2.62g (22.69mmol) of N-hydroxysuccinimide is added, the 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride is added in portions and reacted for 14 hours at room temperature, the mixture is filtered, decompressed and concentrated to obtain a white solid, the filter cake is pulped with 20ml of isopropanol and then filtered, the filter cake is dried in vacuum to obtain 11.65g of the white solid, and the molar yield is 97.1%;
3) synthesis of Val-NCA
Adding 100ml of tetrahydrofuran, 10g (85.36mmol) of valine and 12.67g (42.68mmol) of triphosgene into a 250ml three-necked bottle with a thermometer and a stirrer under stirring, reacting at 50 ℃ for 2h, concentrating under reduced pressure, adding 100ml of petroleum ether after concentrating, pulping for half an hour, filtering, and drying a filter cake in vacuum to obtain 11.62g of white solid with the molar yield of 95.1%;
4) synthesis of H-Val-Lys (Boc) -OH
50ml of water, 40ml of tetrahydrofuran, 2.51g (62.87mmol) of sodium hydroxide and 13.77g (55.89mmol) of LNE- (tert-butoxycarbonyl) -L-lysine ys (Boc) are stirred and dissolved in a 250ml three-necked flask with a thermometer and a stirrer, a cold trap is cooled to 0-5 ℃, Val-NCA10g (69.86mmol) is added while controlling the pH to 10 with a 30% sodium hydroxide solution, the temperature is controlled to 0-5 ℃, after dropping, the temperature is raised to 25 ℃ for reaction for 1 hour, then the pH is adjusted to 2 with 6M hydrochloric acid, 20ml of n-butanol is used for extraction, 20ml of saline is washed with 20ml of 3, magnesium sulfate is added for 5g, the mixture is filtered after stirring for half an hour, and the mixture is concentrated under reduced pressure to obtain 23.26g of oily matter with 96.47 mol yield;
5) synthesis of Pal-Lys (Boc) -Val-Lys (Boc) -OH
50ml of water, 50ml of tetrahydrofuran, 50ml of Pal-lys (boc) -OSu10g (17.19mmol), and H-Val-lys (boc) -Oh7.12g (20.63mmol) were added to a 250ml three-necked flask equipped with a thermometer and a stirrer with stirring, the pH was adjusted to 8.5 with a 30% sodium hydroxide solution, and after 2 hours of reaction, the mixture was concentrated under reduced pressure, adjusted to 2 with 6M hydrochloric acid, extracted with ethyl acetate at 50ml 1, washed with brine at 15ml 3, and concentrated under reduced pressure to give 13.56g of a white solid with a molar yield of 97.2%;
6) synthesis of palmitoyl tripeptide-5
30ml of trifluoroacetic acid, Pal-Lys (Boc) -Val-Lys (Boc) -OH10g (12.53mmol) was added to a 250ml three-necked flask equipped with a thermometer and a stirrer under stirring, and after stirring at room temperature for 2 hours, the resulting mixture was dropped into glacial ethyl ether and filtered to obtain a satisfactory product, and the filter cake was vacuum-dried to obtain a pure white solid (9.68 g) in a molar yield of 92%.
Example 2
1) Synthesis of Pal-Lys (Boc) -OH
In a 500ml three-necked flask equipped with a thermometer and a stirrer, 200ml of water and 21.51g (87.31mmol) of NE- (tert-butoxycarbonyl) -L-lysine were added under stirring, the pH was adjusted to 10 with a 30% sodium hydroxide solution, 20g (72.76mmol) of palmitoyl chloride was added dropwise under stirring, the pH was adjusted to 10 with a 30% sodium hydroxide solution, the reaction was completed at room temperature for 2.5 hours, a large amount of solid was precipitated by adjusting the pH to 2 with 6M hydrochloric acid, the resulting solution was filtered, and the cake was vacuum-dried to obtain 33.57g of a white solid with a molar yield of 95.2%;
2) synthesis of Pal-Lys (Boc) -OSu
Adding 60ml of tetrahydrofuran and 60ml of Pal-Lys (Boc) -OH10g (20.63mmol) into a 250ml three-necked bottle with a thermometer and a stirrer under stirring, cooling to 0-5 ℃, adding HOSu2.62g (22.69mmol), adding 4.75g (24.76mmol) of 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride in batches, reacting for 15 hours at room temperature, filtering, concentrating under reduced pressure to obtain a white solid, pulping a filter cake with 20ml of isopropanol, filtering, and drying the filter cake under vacuum to obtain 11.66g of the white solid with 97.2 mol percent yield;
3) synthesis of Val-NCA
Adding 100ml of tetrahydrofuran, 10g (85.36mmol) of valine and 12.67g (42.68mmol) of triphosgene into a 250ml three-necked bottle with a thermometer and a stirrer under stirring, reacting at 50 ℃ for 2h, concentrating under reduced pressure, adding 100ml of petroleum ether after concentrating, pulping for half an hour, filtering, and drying a filter cake in vacuum to obtain 11.63g of white solid with the molar yield of 95.2%;
4) synthesis of H-Val-Lys (Boc) -OH
50ml of water, 40ml of tetrahydrofuran, 2.51g (62.87mmol) of sodium hydroxide and 13.77g (55.89mmol) of NE- (tert-butoxycarbonyl) -L-lysine are added into a 250ml three-necked flask with a thermometer and a stirrer under stirring, the mixture is stirred to dissolve the clear solution, a cold trap is cooled to 0-5 ℃, H-Val-NCA10g (69.86mmol) is added while controlling the pH to 10 with a 30% sodium hydroxide solution, the mixture is controlled to 0-5 ℃, the mixture is heated to 25 ℃ after dropping, the mixture is reacted for 1.5 hours, then the pH is adjusted to 2 with 6M hydrochloric acid, 20ml of n-butanol is used for extraction, 20ml of brine is washed with 20ml of 3, magnesium sulfate is added for 5g, the mixture is stirred for half an hour and filtered, and the mixture is concentrated under reduced pressure to obtain 23.28g of oily matter with the molar yield of 96.5%;
5) synthesis of Pal-Lys (Boc) -Val-Lys (Boc) -OH
50ml of water, 50ml of tetrahydrofuran, 50ml of Pal-lys (boc) -OSu10g (17.19mmol), and H-Val-lys (boc) -Oh7.12g (20.63mmol) were added to a 250ml three-necked flask equipped with a thermometer and a stirrer with stirring, the pH was adjusted to 8.5 with a 30% sodium hydroxide solution, and after 2 hours of reaction, the mixture was concentrated under reduced pressure, adjusted to 2 with 6M hydrochloric acid, extracted with ethyl acetate at 50ml 1, washed with brine at 15ml 3, and concentrated under reduced pressure to give 13.54g of a white solid with a molar yield of 97.0%;
6) synthesis of palmitoyl tripeptide-5
30ml of trifluoroacetic acid, Pal-Lys (Boc) -Val-Lys (Boc) -OH10g (12.53mmol) was added to a 250ml three-necked flask equipped with a thermometer and a stirrer with stirring, and after stirring at room temperature for 2 hours, the resulting mixture was dropped into glacial ethyl ether and filtered to obtain a satisfactory product, and the filter cake was vacuum-dried to obtain a pure white solid (9.70 g) with a molar yield of 92.2%.
Example 3
1) Synthesis of Pal-Lys (Boc) -OH
In a 500ml three-necked flask equipped with a thermometer and a stirrer, 200ml of water, 21.51g (87.31mmol) of NE- (tert-butoxycarbonyl) -L-lysine, was added under stirring, the pH was adjusted to 10 with a 30% sodium hydroxide solution, 20g (72.76mmol) of palmitoyl chloride was added dropwise under stirring, the pH was adjusted to 10 with a 30% sodium hydroxide solution, the reaction was completed at room temperature for 3 hours, a large amount of solid was precipitated by adjusting the pH to 2 with 6M hydrochloric acid, the resulting solution was filtered, and the cake was vacuum-dried to obtain 33.52g of a white solid with a molar yield of 95.0%;
2) synthesis of Pal-Lys (Boc) -OSu
Adding 60ml of tetrahydrofuran and 60ml of Pal-Lys (Boc) -OH10g (20.63mmol) into a 250ml three-necked bottle with a thermometer and a stirrer under stirring, cooling to 0-5 ℃, adding 2.62g (22.69mmol) of N-hydroxysuccinimide, adding 4.75g (24.76mmol) of 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride in batches, reacting for 16 hours at room temperature, filtering, concentrating under reduced pressure to obtain a white solid, pulping a filter cake with 20ml of isopropanol, filtering, and drying the filter cake under vacuum to obtain 11.64g of the white solid with the molar yield of 97.0 percent;
3) synthesis of Val-NCA
Adding 100ml of tetrahydrofuran, 10g (85.36mmol) of valine and 12.67g (42.68mmol) of triphosgene into a 250ml three-necked bottle with a thermometer and a stirrer under stirring, reacting at 50 ℃ for 2h, concentrating under reduced pressure, adding 100ml of petroleum ether after concentrating, pulping for half an hour, filtering, and drying a filter cake in vacuum to obtain 11.67g of white solid with the molar yield of 95.5%;
4) synthesis of H-Val-Lys (Boc) -OH
50ml of water, 40ml of tetrahydrofuran, 2.51g (62.87mmol) of sodium hydroxide and 13.77g (55.89mmol) of NE- (tert-butoxycarbonyl) -L-lysine are added into a 250ml three-necked flask with a thermometer and a stirrer under stirring, the mixture is stirred to dissolve the clear solution, a cold trap is cooled to 0-5 ℃, Val-NCA10g (69.86mmol) is added while controlling the pH to 10 with 30% sodium hydroxide solution, the material temperature is controlled to 0-5 ℃, the temperature is increased to 25 ℃ after the dropwise addition, the reaction is carried out for 2 hours, then the pH is adjusted to 2 with 6M hydrochloric acid, 20ml of n-butanol is used for extraction, 20ml of brine is washed, 5g of magnesium sulfate is added, the mixture is filtered after stirring for half an hour, and the oily substance is obtained by concentration under reduced pressure, and the molar yield is 96.6 percent;
5) synthesis of Pal-Lys (Boc) -Val-Lys (Boc) -OH
50ml of water, 50ml of tetrahydrofuran, 50ml of Pal-lys (boc) -OSu10g (17.19mmol), and H-Val-lys (boc) -Oh7.12g (20.63mmol) were added to a 250ml three-necked flask equipped with a thermometer and a stirrer with stirring, the pH was adjusted to 8.5 with a 30% sodium hydroxide solution, and after 2 hours of reaction, the mixture was concentrated under reduced pressure, adjusted to 2 with 6M hydrochloric acid, extracted with ethyl acetate to 50ml 1, washed with brine to 15ml 3, and concentrated under reduced pressure to give 13.58g of a white solid with a molar yield of 97.3%;
6) synthesis of palmitoyl tripeptide-5
30ml of tetrahydrofuran, Pal-Lys (Boc) -Val-Lys (Boc) -OH10g (12.53mmol) was added to a 250ml three-necked flask equipped with a thermometer and a stirrer with stirring, and after stirring at room temperature for 2 hours, the resulting mixture was dropped into glacial ethyl ether and filtered to obtain a satisfactory product, and the filter cake was vacuum-dried to obtain 9.71g of a white solid having a purity and a molar yield of 92.3%.
Claims (6)
1. A liquid phase synthesis method of palmitoyl tripeptide-5 is characterized by comprising the following steps:
1) synthesis of Pal-Lys (Boc) -OH:
adding water and NE- (tert-butoxycarbonyl) -L-lysine into a reaction device in sequence under stirring, adjusting the pH to 10 by using a 30% sodium hydroxide solution, controlling the pH to 10 by using a 30% sodium hydroxide solution while dropwise adding palmitoyl chloride, completely controlling the pH to 10, reacting at room temperature, adjusting the pH to 2 to precipitate a large amount of solid, filtering, and drying the solid in vacuum;
2) synthesis of Pal-Lys (Boc) -OSu:
sequentially adding tetrahydrofuran in a reaction device under stirring, sequentially adding Pal-Lys (Boc) -OH obtained in the step 1), cooling to 0-5 ℃, adding N-hydroxysuccinimide, stirring for 10min, adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride in batches, reacting at room temperature, filtering, concentrating under reduced pressure to obtain a white solid, pulping a filter cake with isopropanol, filtering, and drying the solid in vacuum;
3) Val-NCA Synthesis:
adding tetrahydrofuran, valine and triphosgene into a reaction device in turn under stirring, reacting for 2h at 50 ℃, concentrating under reduced pressure, adding petroleum ether after concentrating, pulping, filtering, and drying the solid in vacuum;
4) synthesis of H-Val-Lys (Boc) -OH:
adding water, tetrahydrofuran, sodium hydroxide and NE- (tert-butoxycarbonyl) -L-lysine into a reaction device in sequence under stirring, cooling by a cold trap, adding Val-NCA obtained in the step 3) while controlling the pH to be 11 by using a 30% sodium hydroxide solution, heating for reaction for 1-2h after dropwise addition, adjusting the pH to be 2, extracting by using n-butanol, washing by using brine, drying by using anhydrous magnesium sulfate, and concentrating under reduced pressure to obtain an oily substance;
5) synthesis of Pal-Lys (Boc) Val-Lys (Boc) -OH:
adding water, tetrahydrofuran, Pal-Lys-OSu obtained in the step 2) and H-Val-Lys (boc) -OH obtained in the step 4) into a reaction device, adjusting the pH to 8.5 with a 30% sodium hydroxide solution, reacting at room temperature for 2 hours, concentrating under reduced pressure, adjusting the pH to 2, extracting with ethyl acetate, washing with brine, and concentrating under reduced pressure to obtain a white solid;
6) synthesis of palmitoyl tripeptide-5:
and (3) sequentially adding trifluoroacetic acid and the Pal-Lys (Boc) -Val-Lys (Boc) -OH obtained in the step 5) into a reaction device under stirring, reacting for 2h at room temperature, dripping the material liquid into a crystallization reagent, filtering to obtain a qualified product, and drying the product in vacuum to obtain a white solid.
2. The liquid-phase synthesis method of palmitoyl tripeptide-5 according to claim 1, characterized in that the reaction time in step 1) is controlled to 2-3 hours.
3. The liquid-phase synthesis method of palmitoyl tripeptide-5 according to claim 1, characterized in that the reaction time at room temperature in step 2) is controlled to be 14-16 hours.
4. The liquid-phase synthesis method of palmitoyl tripeptide-5 according to claim 1, characterized in that, in step 4), the temperature of the cold trap is reduced to 0-5 ℃, and after the dropwise addition, the temperature is increased to 25 ± 2 ℃.
5. The method for synthesizing palmitoyl tripeptide-5 according to claim 1, wherein 6M hydrochloric acid is used for adjusting pH 2 in steps 1), 4) and 5).
6. The liquid-phase synthesis method of palmitoyl tripeptide-5 according to claim 1, characterized in that the crystallization reagent used in step 6) is ethyl glacial ether.
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| KR102652375B1 (en) * | 2024-01-15 | 2024-03-28 | 김헌준 | Method for producing magnesium tripeptide-1 |
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