CN115043744A - Preparation method of self-assembled amino acid nano material - Google Patents
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- CN115043744A CN115043744A CN202210711107.1A CN202210711107A CN115043744A CN 115043744 A CN115043744 A CN 115043744A CN 202210711107 A CN202210711107 A CN 202210711107A CN 115043744 A CN115043744 A CN 115043744A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
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- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
- C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto groups
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- C07—ORGANIC CHEMISTRY
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- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
Abstract
The invention discloses a preparation method of a self-assembly amino acid nano material, which takes amino acid as a main body and is formed by combining metal ions with amino and carboxyl of the amino acid, wherein the size of the nano material is 0.1-100 mu m. The preparation method adopts the combination of metal ions and amino and carboxyl of amino acid, effectively realizes self-assembly and forms a stable nano structure.
Description
Technical Field
The invention belongs to the technical field of biological materials, and particularly relates to a preparation method of a self-assembled amino acid nano material.
Background
Nanotechnology refers to the scientific technology of manufacturing substances with single atoms and molecules, and researches the properties and applications of materials with structure sizes in nanometer scale. When the material reaches the nanometer scale, the property of the material is mutated, and special properties appear. The material is a nano material which is composed of atoms and molecules with different compositions and special properties of macroscopic substances.
Amino acids are a generic term for a class of compounds containing both amino and carboxyl groups. It is the most basic substance that constitutes a biological protein and is involved in the life activity, is the basic unit of protein molecules in the body, has close relation with the life activity of the organism, and is one of the essential nutrients in the body. More than 300 natural amino acids have been found, of which 20 amino acids are required by the human body, including non-essential amino acids and essential amino acids (which cannot be synthesized by the human body itself). They can be classified into acidic, basic, neutral, heterocyclic and the like according to their chemical properties.
Self-assembly is the process by which assembly elements spontaneously undergo ordered aggregation through weak interaction forces and their synergistic effects to form assemblies of specific dimensions, structure and function. This process is ubiquitous in the biomass-free world and in the origin, formation, evolution and evolution of the biomass world, such as the formation of cell membranes, DNA double helix structure and protein folding, and is one of the essence of life science.
Molecular self-assembly is the formation of molecular aggregates with a specific order of arrangement by non-covalent interactions, using molecular recognition between molecules or between one fragment and another fragment of a molecule. The traditional polypeptide self-assembly can effectively realize molecular self-assembly by utilizing the hydrogen bond action among peptide bonds of the polypeptide, the hydrogen bond action among amino acid residues, the electrostatic action, the hydrophobic action, the pi-pi stacking action and the like to form the polypeptide nano-particles. Mainly forms structures such as alpha helix, beta sheet, beta turn, disulfide bond and the like which exist in some proteins, and constructs functions based on the structures. The traditional self-assembly method has the limitations that the number of materials which can be successfully self-assembled is small, and the product structure is single. For a single monomer, self-assembly is difficult to achieve, limiting the range of applications for single peptides.
Disclosure of Invention
The invention aims to provide a preparation method of a self-assembly amino acid nano material, which adopts the combination of metal ions and amino and carboxyl of amino acid to effectively realize self-assembly and form a stable nano structure.
The invention adopts the following technical scheme: a self-assembly amino acid nano material takes amino acid as a main body and is formed by combining metal ions with amino and carboxyl of the amino acid, and the size of the nano material is 0.1-100 mu m.
The invention also discloses a preparation method of the self-assembled amino acid nano material, which comprises the following steps:
step one, preparing a mixed solution of an amino acid monomer and metal ions;
step two, mixing the mixed solution in the step one with an organic solvent;
step three, heating the total mixed solution, stirring for reaction, and performing combined self-assembly reaction on the metal ions and amino and carboxyl of amino acid to obtain a nano material suspension;
and step four, centrifuging to remove the supernatant, and obtaining the assembled amino acid nano material.
Further, the mass ratio of the amino acid monomer to the metal ion is (1-10): (2-1).
Further, the amino acid monomer is glycine, alanine, valine, leucine, isoleucine, methionine, proline, tryptophan, serine, tyrosine, cysteine, phenylalanine, asparagine, glutamine, threonine, aspartic acid, glutamic acid, lysine, arginine or histidine.
Further, the metal ion is zinc ion, copper ion, iron ion, ferrous ion, cobalt ion or magnesium ion.
Further, in the second step, the volume ratio of the mixed solution to the organic solvent is 1 (1-9); the pH value of the total mixed solution is 4-11.
Further, the organic solvent is methanol, ethanol or acetic acid.
Further, the heating temperature is 40 ℃ to 90 ℃.
Furthermore, the size of the self-assembly amino acid nano material is 0.1-100 μm.
The invention has the beneficial effects that: in the invention, metal ions are combined with amino and carboxyl of amino acid to obtain the assembled amino acid nano material, so that the problem that a single monomer is not easy to assemble is solved, a complex manufacturing process and a long reaction time are not needed, the capacity can be rapidly improved, and the production cost is reduced.
Drawings
Fig. 1 is a morphology diagram of phenylalanine nanomaterial observed using a scanning electron microscope.
Fig. 2 is a morphological diagram of tryptophan nanomaterial observed using a scanning electron microscope.
Fig. 3 is a morphology of tyrosine nanomaterials observed using a scanning electron microscope.
Fig. 4 is a morphological diagram of leucine nanomaterial observed using a scanning electron microscope.
Fig. 5 is a morphological diagram of cysteine nanomaterial observed using a scanning electron microscope.
Fig. 6 is a morphological diagram of glutamic acid nanomaterial observed using a scanning electron microscope.
Fig. 7 is a morphological diagram of methionine nanomaterial observed using scanning electron microscope.
Fig. 8 is a morphology of asparagine nano-material observed using scanning electron microscope.
Detailed Description
The present invention will be described in detail below with reference to the accompanying drawings and specific embodiments.
When the amino acid is used as a raw material, the amino acid is mostly in a monomer form, or is combined with other molecules by a chemical synthesis method, and the amino acid is a monomer, so that the stability and the slow release property are improved. When the chemical synthesis method is adopted, new substances are introduced, side effects are generated when the chemical synthesis method is used, and the performance of the amino acid is influenced.
The invention discloses a self-assembly amino acid nano material, which is formed by combining metal ions with amino and carboxyl of amino acid; the amino acid is used as a main body, and the amino acid is formed by non-covalent acting forces such as p-pi conjugation, hydrogen bonds and the like between an amino acid monomer and metal ions, so that the amino acid structure is not influenced, and the side effect is avoided. The size of the nano material is 0.1-100 μm. The structural formula is as follows:
the amino acids are twenty kinds of amino acids required by human body, and are respectively glycine, alanine, valine, leucine, isoleucine, methionine (methionine), proline, tryptophan, serine, tyrosine, cysteine, phenylalanine, asparagine, glutamine, threonine, aspartic acid, glutamic acid, lysine, arginine or histidine.
The metal ion is zinc ion, copper ion, iron ion, ferrous ion, cobalt ion or magnesium ion. The metal ions all belong to positive valence metal ions, and can form effective metal ion coordination with amino acid so as to assemble different nano materials. The metal ions are mainly combined with amino and carboxyl of amino acid to realize self-assembly, so that all basic amino acid can be self-assembled into the nano material. The metal ions all belong to positive divalent metal ions, so that the metal ions and amino acid can form effective metal ion coordination to assemble different nano materials.
The preparation method of the self-assembled amino acid nano material comprises the following steps:
step one, preparing a mixed solution of an amino acid monomer and metal ions, wherein a solvent is ultrapure water;
the mass ratio of the amino acid monomer to the metal ion is (1-10): (2-1).
Step two, mixing the mixed solution in the step one with an organic solvent; adjusting the pH of the total mixed solution to 4-11;
the organic solvent is methanol, ethanol or acetic acid; the volume ratio of the mixed solution to the organic solvent is 1 (1-9).
Step three, heating the total mixed solution, stirring, and carrying out combined self-assembly reaction on the metal ions and amino and carboxyl of amino acid to obtain a nano material suspension; the heating temperature is 40-90 ℃; the synthesis time is 10-100 minutes.
And step four, centrifuging to remove the supernatant, and obtaining the assembled amino acid nano material. The centrifugal speed is 14000r/min, and the centrifugation times are 3.
Example 1
16.5mg of phenylalanine monomer was dissolved in 1mL of ultrapure water, and 6.8mg of ZnCl was added 2 Dissolved in 1mL of methanol, the ratio of the amounts of phenylalanine to zinc ion species was 2: 1, mixing the two solutions, adding 8mL of methanol to make the total volume 10mL, and adjusting the pH to 10 with 1M NaOH solution. And (3) putting the reaction solution into a room-temperature water bath kettle, stirring and heating to 85 ℃, evaporating methanol until the volume of the system is 1mL, and cooling to room temperature. Room temperature refers to the temperature of the environment in which the reaction is conducted, and is typically 25 ℃. Centrifuging at 14000rpm for 10min, discarding supernatant, adding 1mL ultrapure water for resuspending, and repeating for three times. As a result of observation by a Scanning Electron Microscope (SEM), as shown in FIG. 1, phenylalanine and zinc ions are combined to form a rod-like nanomaterial having a diameter of 0.5 to 5 μm and a length of 20 to 80 μm.
Example 2
This example differs from example 1 in that copper ions were selected, 16.5mg of phenylalanine monomer was dissolved in 1mL of ultrapure water, and 3.2mg of CuSO was added 4 Dissolved in 1mL of methanol, the ratio of the amounts of carnosine to zinc ion species was 5: 1, mixing the two solutions, adding 8mL of methanol to make the total volume 10mL, and adjusting the pH to 8 with 1M NaOH solution. And (3) putting the reaction solution into a room-temperature water bath kettle, stirring and heating to 60 ℃, evaporating methanol until the volume of the system is 1mL, and cooling to room temperature. Room temperature refers to the temperature of the environment in which the reaction is conducted, and is typically 25 ℃. Centrifuging at 14000rpm for 10min, discarding the supernatant, adding 1mL of ultrapure water for resuspension, and repeating for three times to obtain the final product.
Example 3
This example differs from example 1 in that tryptophan was selected and 10.2mg of tryptophan monomer was dissolvedIn 1mL of ultrapure water, 6.8mg of ZnCl was added 2 Dissolved in 1mL of methanol, the ratio of the amounts of carnosine to copper ion species was 1: 1, mixing the two, adding 4mL of methanol to make the total volume be 6mL, adjusting the pH value to 8 by using 1M NaOH solution, putting the reaction solution into a room-temperature water bath kettle, stirring and heating to 90 ℃, evaporating the methanol until the system is 1mL, cooling to room temperature, and centrifuging to obtain the product. As a result of observation by a Scanning Electron Microscope (SEM), as shown in FIG. 2, tryptophan was combined with zinc ions to form a rod-like nanomaterial having a diameter of 0.3 to 3 μm and a length of 10 to 40 μm.
Example 4
This example differs from example 1 in that tyrosine was chosen, 18.1mg of tyrosine monomer was dissolved in 1mL of ultra pure water, and 1.36mg of ZnCl was added 2 The ratio of the amount of tyrosine to the amount of zinc ion in 1mL of ethanol was 10: 1, mixing the two solutions uniformly to make the total volume be 2mL, adjusting the pH value to 8 by using a 1M NaOH solution, putting the reaction solution into a room-temperature water bath kettle, stirring and heating to 60 ℃, evaporating ethanol until the system is 1mL, cooling to room temperature, and centrifuging to obtain the compound. As a result of observation by using a Scanning Electron Microscope (SEM), as shown in FIG. 3, tyrosine was combined with zinc ions to form a rod-like nanomaterial having a diameter of 0.3 to 10 μm and a length of 10 to 150 μm
Example 5
This example differs from example 1 in that iron ions were selected, 16.5mg of phenylalanine monomer was dissolved in 1mL of ultrapure water, and 4.1mg of FeCl was added 3 Dissolved in 1mL of methanol, the ratio of the amounts of carnosine to zinc ion species was 4: 1, mixing the two solutions, adding 8mL of methanol to make the total volume 10mL, and adjusting the pH to 9 with 1M NaOH solution. And (3) putting the reaction solution into a room-temperature water bath kettle, stirring and heating to 90 ℃, evaporating methanol until the volume of the system is 1mL, and cooling to room temperature. Centrifuging at 14000rpm for 10min, discarding the supernatant, adding 1mL of ultrapure water for resuspension, and repeating for three times to obtain the final product.
Example 6
This example differs from example 1 in that leucine was selected, 13.1mg of leucine monomer was dissolved in 1mL of ultra pure water, and 13.6mg of ZnCl was added 2 Dissolved in 1mL of acetic acid, the ratio of the amounts of leucine to zinc ion is1: 1, mixing the two, adding 2mL of acetic acid to make the total volume be 4mL, adjusting the pH value to be 6 by using a 1M NaOH solution, putting the reaction solution into a room-temperature water bath kettle, stirring and heating to 75 ℃, evaporating the acetic acid until the volume of the system is 1mL, and cooling to room temperature. And (5) centrifuging to obtain the product. As a result of observation with a Scanning Electron Microscope (SEM), as shown in FIG. 4, leucine was combined with zinc ions to produce a sheet-like nanomaterial having a diameter of 10 to 50 μm.
Example 7
This example differs from example 1 in that cysteine was selected, 12.1mg of cysteine monomer was dissolved in 1mL of ultrapure water, and 4.4mg of ZnCl was added 2 Dissolved in 1mL of methanol, the ratio of the amounts of cysteine to zinc ion substances was 3: 1, mixing the two, adding 6mL of methanol to make the total volume be 8mL, adjusting the pH value to 9 by using 1M NaOH solution, putting the reaction solution into a room-temperature water bath kettle, stirring and heating to 80 ℃, evaporating the methanol until the system is 1mL, cooling to room temperature, and centrifuging to obtain the product. As a result of observation using a Scanning Electron Microscope (SEM), as shown in FIG. 5, cysteine was combined with zinc ions to produce spherical nanomaterials having diameters of 0.2 to 2 μm.
Example 8
This example differs from example 1 in that aspartic acid was selected, 13.2mg of the aspartic acid monomer was dissolved in 1mL of ultrapure water, and 13.6mg of ZnCl was added 2 The ratio of the amount of aspartic acid to zinc ion in 1mL of ethanol was 1: 1, mixing the two solutions uniformly to make the total volume be 2mL, adjusting the pH value to 10 by using a 1M NaOH solution, putting the reaction solution into a room-temperature water bath kettle, stirring and heating to 60 ℃, evaporating ethanol until the system is 1mL, cooling to room temperature, and centrifuging to obtain the compound.
Example 9
This example differs from example 1 in that glutamic acid was selected, 14.7m glutamic acid monomer was dissolved in 1mL ultrapure water, and 3.4mg ZnCl was added 2 The ratio of the amount of glutamic acid to zinc ion dissolved in 1mL of methanol was 4: 1, mixing the two, adding 8mL of methanol, adjusting the pH value to 8 by using a 1M NaOH solution, putting the reaction solution into a room-temperature water bath kettle, stirring and heating to 85 ℃, evaporating the methanol until the concentration of the system is 1mL, cooling to room temperature,and (4) centrifuging to obtain the product. As a result of observation with a Scanning Electron Microscope (SEM), as shown in FIG. 6, glutamic acid was combined with zinc ions to produce a particulate nanomaterial having a diameter of 0.5 to 3 μm.
Example 10
This example differs from example 1 in that lysine was selected, 14.6mg of lysine monomer was dissolved in 1mL of ultrapure water, and 20.4mg of ZnCl was added 2 The ratio of the amount of glutamic acid to zinc ion dissolved in 1mL of methanol was 1: 1.5, mixing the two, adding 8mL of methanol, adjusting the pH to 6.5 by using a 1M NaOH solution, putting the reaction solution into a room-temperature water bath kettle, stirring and heating to 50 ℃, evaporating the methanol until the system is 1mL, cooling to room temperature, and centrifuging to obtain the product.
Example 11
This example differs from example 1 in that methionine was chosen, 14.9mg of methionine monomer was dissolved in 1mL of ultrapure water, 6.8mg of ZnCl2 was dissolved in 1mL of ethanol, and the ratio of the amounts of methionine to zinc ion species was 2: 1, mixing the two, adding 6mL of ethanol, adjusting the pH value to 10 by using a 1M NaOH solution, putting the reaction solution into a room-temperature water bath kettle, stirring and heating to 60 ℃, evaporating the ethanol until the volume of the system is 1mL, cooling to room temperature, and centrifuging to obtain the compound. As a result of observation by a Scanning Electron Microscope (SEM), as shown in FIG. 7, methionine was combined with zinc ions to produce a sheet-like nanomaterial having a length of 20 to 60 μm and a width of 3 to 10 μm.
Example 12
This example differs from example 1 in that asparagine was chosen, 13.2mg of asparagine monomer was dissolved in 1mL of ultrapure water, and 13.6mg of ZnCl was added 2 Dissolved in 1mL of acetic acid, the ratio of the amount of asparagine to the amount of zinc ion material is 1: 1, mixing the two solutions uniformly to make the total volume be 2mL, adjusting the pH value to 8 by using a 1M NaOH solution, putting the reaction solution into a room-temperature water bath kettle, stirring and heating to 40 ℃, evaporating acetic acid until the system is 1mL, cooling to room temperature, and centrifuging to obtain the compound. As a result of observation by using a Scanning Electron Microscope (SEM), as shown in FIG. 8, asparagine is combined with zinc ions to form a flaky nanomaterial with a length of 5 to 15 μm and a width of 0.3 to 3 μm.
Example 13
This example differs from example 1 in that glutamine was chosen, 14.6mg of glutamine monomer was dissolved in 1mL of ultrapure water, and 2.72mg of ZnCl was added 2 Dissolved in 1mL of methanol, the ratio of the amount of the substance of glutamine and zinc ions was 5: 1, mixing the two, adding 4mL of methanol, adjusting the pH value to 7 by using a 1M NaOH solution, putting the reaction solution into a room-temperature water bath kettle, stirring and heating to 80 ℃, evaporating the methanol until the volume of the system is 1mL, cooling to room temperature, and centrifuging to obtain the catalyst.
Example 14
This example differs from example 1 in that arginine was selected, 17.4mg of arginine monomer was dissolved in 1mL of ultra pure water, and 6.8mg of ZnCl was added 2 The ratio of the amount of arginine to the amount of zinc ions in 1mL of ethanol was 2: 1, mixing the two, adding 8mL of ethanol, adjusting the pH value to 10 by using a 1M NaOH solution, putting the reaction solution into a room-temperature water bath kettle, stirring and heating to 90 ℃, evaporating the ethanol until the volume of the system is 1mL, cooling to room temperature, and centrifuging to obtain the compound.
Because the self-assembly of peptide has requirements on sequence, the amino acid structure is simple, the reaction sites of single amino acid are few, and the peptide is not easy to assemble, in the invention, the nano material is formed by non-covalent acting forces such as p-pi conjugation, hydrogen bonds and the like between amino acid monomers and metal ions.
Claims (9)
1. The self-assembly amino acid nano material is characterized in that amino acid is taken as a main body, and is formed by combining metal ions with amino groups and carboxyl groups of the amino acid, and the size of the nano material is 0.1-100 mu m.
2. The method for preparing a self-assembled amino acid nanomaterial as claimed in claim 1, wherein the method comprises the following steps:
step one, preparing a mixed solution of an amino acid monomer and metal ions;
step two, mixing the mixed solution in the step one with an organic solvent;
step three, heating the total mixed solution, stirring for reaction, and carrying out combined self-assembly reaction on the metal ions and amino and carboxyl of amino acid to obtain a nano material suspension;
and step four, centrifuging to remove the supernatant, and obtaining the assembled amino acid nano material.
3. The method for preparing the self-assembled amino acid nano material as claimed in claim 2, wherein the mass ratio of the amino acid monomer to the metal ion is (1-10): (2-1).
4. The method for preparing a self-assembled amino acid nanomaterial according to claim 2 or 3, wherein the amino acid monomer is glycine, alanine, valine, leucine, isoleucine, methionine, proline, tryptophan, serine, tyrosine, cysteine, phenylalanine, asparagine, glutamine, threonine, aspartic acid, glutamic acid, lysine, arginine, or histidine.
5. An X according to claim 4, wherein said metal ions are zinc ions, copper ions, iron ions, ferrous ions, cobalt ions or magnesium ions.
6. The method for preparing the self-assembled amino acid nano material as claimed in claim 5, wherein in the second step, the volume ratio of the mixed solution to the organic solvent is 1 (1-9); the pH value of the total mixed solution is 4-11.
7. The method of claim 6, wherein the organic solvent is methanol, ethanol or acetic acid.
8. The method for preparing self-assembled amino acid nanomaterial of claim 7, wherein the heating temperature is 40 ℃ to 90 ℃.
9. The method for preparing the self-assembled amino acid nano material as claimed in claim 8, wherein the size of the self-assembled amino acid nano material is 0.1-100 μm.
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