CN113061111A - Method for preparing amino acid compound with photocrosslinking activity - Google Patents
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Abstract
The invention discloses a preparation method of amino acid compounds with photo-crosslinking activity, which relates to the technical field of biological medicine and comprises the steps of preparing 3- (3-butyn-1-yl) -3H-bisaziridine-3-ethanol from 1-hydroxy-3-ketoheptyne; further reacting with iodine and triphenylphosphine to give 3- (3-yne-1-butyl) -3- (2-iodoethyl) -3H-bisaziridine, further reacting with potassium cyanide to give 3- (3- (but-3-ynyl) -3H-bisaziridin-3-yl) propionitrile, reacting in aqueous sodium hydroxide solution to give 3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionic acid, and further reacting with 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride and N-hydroxysuccinimide to give 2, 5-dioxopyrrolidin-1-yl 3- (3- (but-3-yn-1-yl) -3H-bisaziridine -3-yl) propionate, and then respectively reacts with amino acid molecules to generate target products. The preparation process provided by the invention is simpler, and the amino acid compound contains a bis-aziridine group with higher photoaffinity activity.
Description
Technical Field
The invention relates to the technical field of biological medicines, in particular to a preparation method of an amino acid compound with photo-crosslinking activity.
Background
Photocrosslinkers are important tools for chemical biological research and typically comprise photoreactive groups and responsive groups, which, under uv irradiation, are activated to mediate the irreversible linkage between the protein and the ligand. The small molecule connecting photocrosslinking agent can promote the irreversible combination with the protein target, if the small molecule is an amino acid molecule, the amino acid small molecule can be promoted to be combined with the protein target at a specific site, and a chemically stable and crosslinked protein-probe compound is generated, so that the protein-probe compound can be used for various downstream biological activity tests and analyses.
Amino acid is a basic unit for constituting protein, and the preparation of the amino acid compound with photo-crosslinking activity has important application significance for the research in the field based on the special structure-activity relationship between amino acid molecules and protein structures, and can effectively probe the action condition of the amino acid compound on intracellular protein. Researchers at present have found and can prepare various groups containing photo-crosslinking activity, such as phenyl azide, benzophenone and the like, but the photo-crosslinking activity of the groups is not high, and few studies on amino acid compounds with photo-crosslinking activity are currently carried out, the preparation process is complicated, and some additional intermediate reagents need to be synthesized.
Disclosure of Invention
The invention aims to provide a preparation method of amino acid compounds with photo-crosslinking activity, which has simple preparation process and does not need to additionally synthesize some intermediate reagents, and the obtained amino acid compounds contain bis-aziridine groups with higher photo-crosslinking activity, so that the amino acid compounds have higher sensitivity in subsequent research and use. The technical effects that can be produced by the preferred technical scheme in the technical schemes provided by the invention are described in detail in the following.
In order to achieve the purpose, the invention provides the following technical scheme:
the invention provides a preparation method of amino acid compounds with photo-crosslinking activity, which comprises the following steps:
1) mixing 1-hydroxy-3-ketoheptyne with anhydrous ammonia under the condition of acetone-dry ice bath, stirring and reacting for 5h at the temperature of 35-40 ℃, cooling the mixed solution, adding an anhydrous methanol solution of hydroxylamine-O-sulfonic acid into the mixed solution within 30min, refluxing and stirring for 1h, evaporating the residual ammonia, filtering to obtain a suspension, evaporating the solvent, dissolving with dichloromethane, treating with triethylamine, slowly adding a dichloromethane solution of iodine until a persistent orange brown color appears, and separating by column chromatography to obtain a compound 1;
2) under the ice bath condition, imidazole and triphenylphosphine are added into dichloromethane and fully stirred and dissolved, then, iodine and dichloromethane solution of a compound 1 are added into the mixture, the mixture is stirred and reacted for 4 hours under the condition of keeping out of the sun, and Na is added for reaction2S2O3Quenching the aqueous solution, extracting the aqueous layer with ethyl acetate, washing the obtained mixed organic layer with saturated saline, drying with anhydrous sodium sulfate, and removing the solvent in vacuum to obtain a compound 2;
3) dissolving the compound 2 in DMF (N, N-dimethylformamide), adding potassium cyanide into the solution, stirring under heating for reaction, then quenching with water, extracting with ethyl acetate, washing the obtained organic layer with saturated saline solution, drying with anhydrous sodium sulfate, removing the solvent, and separating by column chromatography to obtain a compound 3;
4) adding compound 3 into aqueous solution of sodium hydroxide, adding ether, separating water layer, acidifying with aqueous solution of hydrochloric acid, extracting water layer with ethyl acetate, drying with anhydrous sodium sulfate, filtering, and evaporating under reduced pressure to obtain compound 4;
5) dissolving the compound 4 and N-hydroxysuccinimide in DMF, adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride under the conditions of nitrogen atmosphere and ice bath, gradually heating to room temperature for reaction, and washing and separating to obtain a compound 5;
6) mixing water and 1, 4-dioxane at a volume ratio of 1:1 as a solvent, adding sodium bicarbonate to make the solvent alkaline, adding compound 5 and histidine or isoleucine into the alkaline solvent to react to generate (3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionyl) histidine (X1) or (3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionyl) isoleucine (X2); triethylamine was added to the acetonitrile solvent to treat the reaction product, and then compound 5 was added to react with cysteine to produce (3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionyl) cysteine (X3).
Preferably, the compound 3 and the aqueous solution of sodium hydroxide in the step 4) need to be refluxed after being mixed, and the refluxing time is 7 hours.
Preferably, the specific steps of washing and separating in the step 5) are as follows: and adding ethyl acetate into the mixture obtained by the reaction for dissolving, washing with water, washing with a hydrochloric acid aqueous solution, washing with saturated salt water, drying with anhydrous sodium sulfate, removing the solvent by rotation, and separating by adopting a column chromatography to obtain the compound 5.
In the technical scheme provided by the invention, the preparation method of the amino acid compound with the photo-crosslinking activity comprises the steps of mixing 1-hydroxy-3-ketoheptyne with anhydrous ammonia, adding hydroxylamine-O-sulfonic acid for reaction, treating an obtained product by triethylamine, adding iodine for reaction to generate a compound 1, adding imidazole and triphenylphosphine into dichloromethane, reacting with a dichloromethane solution of iodine and the compound 1 to generate a compound 2, reacting the compound 2 with potassium cyanide to generate a compound 3, adding a sodium hydroxide aqueous solution into the compound 3 to obtain a compound 4, dissolving the compound 4 and N-hydroxysuccinimide into DMF, adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride for reaction to generate a compound 5, and reacting the compound 5 with histidine or isoleucine or cysteine to obtain the corresponding amino acid compound with the photo-crosslinking activity. According to the arrangement, the preparation process is simple, some intermediate reagents do not need to be additionally synthesized, and the obtained amino acid compound contains the bis-aziridine group with high photo-crosslinking activity, so that the amino acid compound has higher sensitivity in subsequent research and use.
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In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a synthesis scheme of amino acid compounds having photocrosslinking activity according to an embodiment of the present invention.
In the figure: compound 1 is 3- (3-butyn-1-yl) -3H-bisaziridin-3-ethanol, compound 2 is 3- (3-yn-1-butyl) -3- (2-iodoethyl) -3H-bisaziridine, compound 3 is 3- (3- (but-3-ynyl) -3H-bisaziridin-3-yl) propionitrile, compound 4 is 3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionic acid, compound 5 is 2, 5-dioxopyrrolidin-1-yl 3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionate, x1 is (3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionyl) histidine, X2 is (3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionyl) isoleucine, and X3 is (3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionyl) cysteine.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without any inventive step, are within the scope of the present invention.
The purpose of the present embodiment is to provide a method for preparing an amino acid compound with photo-crosslinking activity, which solves the problems that the current preparation process is complicated, some intermediate reagents need to be additionally synthesized, and the photo-crosslinking activity of the contained photo-affinity groups is not high.
Hereinafter, embodiments will be described with reference to the drawings. The embodiments described below do not limit the contents of the invention described in the claims. The entire contents of the configurations shown in the following embodiments are not limited to those required as solutions of the inventions described in the claims.
Referring to fig. 1, the method for preparing amino acid compounds with photo-crosslinking activity includes the following steps.
1-hydroxy-3-ketoheptyne (2.52g, 20mmol) was charged into a round-bottomed flask, and anhydrous ammonia (20ml) was condensed in the round-bottomed flask under acetone-dry ice bath. The mixture was stirred at a temperature of 35-40 ℃ for 5 hours, the solution was cooled with dry ice and an anhydrous solution of hydroxylamine-O-sulfonic acid (2.59g, 23mmol) was added over 30 minutesMethanol (6ml) solution and the mixture was stirred at reflux for 1 hour at 35 ℃. Then, the remaining ammonia gas was evaporated overnight, filtered to give a suspension, and the filter cake was washed several times with methanol while filtering. The suspension was evaporated in vacuo to remove solvent and was taken up in dichloromethane (10ml) and treated with triethylamine (3.5ml) and a solution of iodine (3.7g, 28.8mmol) in dichloromethane (10ml) was added slowly with stirring until a persistent orange-brown colour appeared. The resulting mixture was chromatographed on a silica gel column through a dichloromethane-hexane (volume ratio 4:1) eluent, and the silica gel column was further washed with a 5% diethyl ether-containing dichloromethane phase to obtain compound 1. Wherein the structural formula of the 1-hydroxy-3-ketoheptyne is as follows:
compound 1 is 3- (3-butyn-1-yl) -3H-bisaziridine-3-ethanol, of the formula:
imidazole (359mg, 5.27mmol) and triphenylphosphine (509mg, 1.94mmol) were dissolved well in dichloromethane (15ml) under ice bath conditions (0 ℃ C.), and iodine (536mg, 2.11mmol) was added to the mixed solvent. The solution was stirred for 5 minutes and a solution of compound 1(242mg, 1.76mmol) in dichloromethane was added slowly. The mixture was stirred for 4 hours under protection from light. Adding Na2S2O3Was quenched, and the aqueous layer was extracted with ethyl acetate. The obtained mixed organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to give the crude product. The crude product was purified by flash column chromatography (hexane: ethyl acetate 20: 1) to afford compound 2 as a colorless oil. Compound 2 is 3- (3-yne-1-butyl) -3- (2-iodoethyl) -3H-bisaziridine, having the formula:
compound 2(1.23g, 5.0mmol) was dissolved in DMF, potassium cyanide (0.64g, 0.01mol) was added to the solution, and the mixture was stirred at 70 ℃The reaction was allowed to react for 10 hours and then quenched with water. Subsequently, the mixture was extracted with ethyl acetate to obtain an organic phase, which was washed with saturated brine and dried over anhydrous sodium sulfate. Removal of the solvent gave the crude product which was purified by flash column chromatography (hexane: ethyl acetate 5: 1) to give compound 3 as a colorless oil. Compound 3 is 3- (3- (but-3-ynyl) -3H-bisaziridin-3-yl) propionitrile, having the formula:
NaOH solution (10ml, 10%) was added to compound 3(0.88g, 6.0mmol), and after compound 3 was mixed with sodium hydroxide, the mixture was refluxed for 7 hours, and then diethyl ether was added to the mixture. The aqueous layer was separated and acidified with hydrochloric acid solution. The aqueous layer was extracted with ethyl acetate, and the resulting mixed organic phase was dried over anhydrous sodium sulfate, filtered, and evaporated to dryness under reduced pressure to give compound 4. Compound 4 is 3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionic acid, of the formula:
dissolving compound 4 and N-hydroxysuccinimide in DMF, adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride into the mixture under the condition of ice bath (0 ℃) by using nitrogen as a protective gas, and gradually raising the temperature to room temperature for reaction for 16 hours. Washing and separating to obtain the compound 5. Compound 5 is 2, 5-dioxopyrrolidin-1-yl 3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionate having the formula:
wherein, the specific steps of washing and separating are as follows: and adding ethyl acetate into the mixture obtained by the reaction to dissolve the mixture, washing the mixture with water, washing the mixture with hydrochloric acid aqueous solution for three times, washing the mixture with saturated salt water, drying the mixture with anhydrous sodium sulfate, removing the solvent by rotation, and purifying the mixture by a silica gel column chromatography to obtain the compound 5.
Dissolving histidine in waterAnd 1, 4-dioxane in a volume ratio of 1:1, adding sodium bicarbonate to make the solution alkaline, adding compound 5, and stirring at room temperature for reaction for at least 12 hr. The solvent was removed by rotary removal in vacuo, filtered and rinsed several times with methanol. The filtrate was collected, spun-dried in vacuo and purified by high performance liquid chromatography to give (3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionyl) histidine, of the formula:
isoleucine is dissolved in a mixed solvent of water and 1, 4-dioxane, the volume ratio of the water to the 1, 4-dioxane is 1:1, sodium bicarbonate is added to make the solution alkaline, then compound 5 is added, and the reaction is stirred at room temperature for at least 12 hours. The solvent was removed in vacuo and extracted with water and ethyl acetate, the organic phase was retained, the solvent was dried and purified by high performance liquid chromatography to give (3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionyl) isoleucine, of the formula:
cysteine, triethylamine and compound 5 were dissolved in 5ml of acetonitrile solvent and the reaction was stirred at room temperature for at least 12 hours. The solvent was removed by rotary removal in vacuo, filtered and rinsed several times with methanol. The filtrate was collected, spun-dried in vacuo and purified by high performance liquid chromatography to give (3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionyl) cysteine of the formula:
through the preparation process, three amino acid compounds with photo-crosslinking activity are obtained, and certainly, the amino acid is changed into other amino acid with the same reactive group as that of the amino acid in the invention, so that other amino acid compounds can be obtained. The preparation method is simple, other intermediate reactants do not need to be additionally synthesized, and the obtained amino acid compounds with photo-crosslinking activity all contain bisaziridine groups and have higher photo-reactivity.
It is understood that the same or similar parts in the above embodiments may be mutually referred to, and the same or similar parts in other embodiments may be referred to for the content which is not described in detail in some embodiments. The multiple schemes provided by the invention comprise basic schemes, are independent from each other and are not restricted with each other, but can be combined with each other under the condition of no conflict, so that multiple effects are realized together.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.
Claims (3)
1. A method for preparing amino acid compounds with photocrosslinking activity is characterized by comprising the following steps:
1) mixing 1-hydroxy-3-ketoheptyne with anhydrous ammonia under the condition of acetone-dry ice bath, stirring and reacting for 5h at the temperature of 35-40 ℃, cooling the mixed solution, adding an anhydrous methanol solution of hydroxylamine-O-sulfonic acid into the mixed solution within 30min, refluxing and stirring for 1h, evaporating the residual ammonia, filtering to obtain a suspension, evaporating the solvent, dissolving with dichloromethane, treating with triethylamine, slowly adding a dichloromethane solution of iodine until a persistent orange brown color appears, and separating by column chromatography to obtain a compound 1;
2) under the ice bath condition, imidazole and triphenylphosphine are added into dichloromethane and fully stirred and dissolved, then, iodine and dichloromethane solution of a compound 1 are added into the mixture, the mixture is stirred and reacted for 4 hours under the condition of keeping out of the sun, and Na is added for reaction2S2O3Quenching the aqueous solution, extracting the aqueous layer with ethyl acetate, washing the obtained mixed organic layer with saturated saline, drying with anhydrous sodium sulfate, and removing the solvent in vacuum to obtain a compound 2;
3) dissolving the compound 2 in DMF, adding potassium cyanide into the solution, stirring under heating for reaction, then quenching with water, extracting with ethyl acetate, washing the obtained organic layer with saturated saline solution, drying with anhydrous sodium sulfate, removing the solvent, and separating by column chromatography to obtain a compound 3;
4) adding compound 3 into aqueous solution of sodium hydroxide, adding ether, separating water layer, acidifying with aqueous solution of hydrochloric acid, extracting water layer with ethyl acetate, drying with anhydrous sodium sulfate, filtering, and evaporating under reduced pressure to obtain compound 4;
5) dissolving the compound 4 and N-hydroxysuccinimide in DMF, adding 1-ethyl- (3-dimethylaminopropyl) carbodiimide hydrochloride under the conditions of nitrogen atmosphere and ice bath, gradually heating to room temperature for reaction, and washing and separating to obtain a compound 5;
6) mixing water and 1, 4-dioxane at a volume ratio of 1:1 as a solvent, adding sodium bicarbonate to make the solvent alkaline, adding compound 5 and histidine or isoleucine into the alkaline solvent to react to generate (3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionyl) histidine (X1) or (3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionyl) isoleucine (X2); triethylamine was added to the acetonitrile solvent to treat the reaction product, and then compound 5 was added to react with cysteine to produce (3- (3- (but-3-yn-1-yl) -3H-bisaziridin-3-yl) propionyl) cysteine (X3).
2. The method for producing an amino acid compound having a photocrosslinking activity according to claim 1, wherein the compound 3 and the aqueous solution of sodium hydroxide are mixed in the step 4) and then refluxed, and the back-refluxing time is 7 hours.
3. The method for preparing amino acids with photocrosslinking activity according to claim 1, wherein the specific washing and separating step in step 5) is: and adding ethyl acetate into the mixture obtained by the reaction for dissolving, washing with water, washing with a hydrochloric acid aqueous solution, washing with saturated salt water, drying with anhydrous sodium sulfate, removing the solvent by rotation, and separating by adopting a column chromatography to obtain the compound 5.
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