CN106749523A - A kind of method that utilization stapler self-assembling polypeptide forms nanotube - Google Patents
A kind of method that utilization stapler self-assembling polypeptide forms nanotube Download PDFInfo
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- CN106749523A CN106749523A CN201611061692.6A CN201611061692A CN106749523A CN 106749523 A CN106749523 A CN 106749523A CN 201611061692 A CN201611061692 A CN 201611061692A CN 106749523 A CN106749523 A CN 106749523A
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- C—CHEMISTRY; METALLURGY
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- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
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- B—PERFORMING OPERATIONS; TRANSPORTING
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Abstract
The invention provides a kind of method that utilization stapler self-assembling polypeptide forms nanotube, including the step of 2 carbon R of side chain for synthesizing Fmoc protections chiral alpha-non-natural amino acid；Alpha-non-natural amino acid is connected with resin using the method for solid-phase synthetic peptide; then proceed to connect 3 amino acid; cysteine is connected again; and the aminoterminal of cysteine is closed with acetyl group; the sulfhydryl protected base of cysteine is removed, then 2 polypeptide compounds of carbon chiral zinc porphyrin of side chain are obtained by intramolecular sulfydryl alkene reaction；Polypeptide is shear off from resin, purified, freezed, obtain white powdery solids；White powdery solids are disperseed with ultra-pure water, ultrasound obtains the peptide Nanotubes of self assembly.The invention provides a kind of new self-assembling polypeptide nanotube, the nanotube be noteworthy characterized by composition nanotube elementary cell be helical structure, the polypeptide spiral be by side chain accurately chiral centre regulation and control realize.
Description
Technical field：
The invention belongs to bioengineering field, it is related to a kind of nanotube, it is specifically a kind of to utilize stapler polypeptide certainly
The method that assembling forms nanotube.
Background technology：
Nano material refers at least one-dimensional in nano-scale (0.1-100nm) or by their conducts in three dimensions
The material that elementary cell is constituted.Nano material makes it have the thing dramatically different with macroscopic material due to unique architectural characteristic
Rationality matter, including：Surface and interfacial effect, small-size effect, quantum size effect, and macro quanta tunnel effect.Recently
Decades, the research of nano science achieves huge progress, and nanometer science and technology has penetrated into us and studied and live
Various aspects.Nanometer technology has become one of change most important technology of human lives.
With Graphene, CNT be the nano material of representative in materialogy, chemistry, biology, medical science etc. each
Ambit achieves good application and popularization.Although nanosecond science and technology achieve unprecedented huge advance, exploitation
New nano material, expands the application depth and range of nanosecond science and technology, is still the target that whole world scientist makes joint efforts.Return
Turn round and look at past 30 years, inorganic nano material is advanced by leaps and bounds, by contrast, the development phase shape of Bio-Nano-Materials is shown in
It is inadequate.Reason is many.First, the operability of biomaterial is more fragile than inorganic material.Biomaterial be usually by
Protein, nucleic acid, or carbohydrate decile is molecular, and the ability of these materials resistance extreme condition is weaker.Secondly, biomaterial
It is more difficult in synthesis.Therefore, enough quality progressive Quality Research to be obtained very difficult.3rd, biomaterial
Activity keep often related to specific condition, and the change of condition can cause the change of structure, cause property to change
Become.
Due to above reason, the research stagnation of Bio-Nano-Materials is result in indirectly.But, Bio-Nano-Materials tool
There is the property for being totally different from inorganic material.Bio-Nano-Materials have complicated space structure, unique electrical and optical property
Matter, and good bio-compatibility and degradability so that Bio-Nano-Materials are in photocatalysis, and electricity is biomedical,
Biomimetic material, and the various fields such as life science are showed one's capabilities.
Inside common Bio-Nano-Materials, the material with polypeptide as representative is most paid attention to.Polypeptide is a class by amino
The biomolecule that acid is connected by amido link.Due to the rich and peptide modified diversity of amino acid so that polypeptide
Composition form is extremely abundant.Usually contained in peptide molecule in the donor and acceptor, and side chain of abundant hydrogen bond comprising conjugation
Electron system, meanwhile, the salt bridge that acid and amino are formed so that the spontaneous form for being assembled into supermolecule of peptide molecule is quite general
Time.This kind of system includes Amphiphilic peptide, and beta folds class polypeptide, the alternate polypeptide of D, L, the collagen bodies of spiral composition
System, and based on dipeptides FF etc..At present, this kind of self-assembling polypeptide nano material is achieved in above-mentioned field and widely should
With.
How polypeptide backbone is based on, builds more complicated, the more special nano material of property, become scientist's effort
A target.By trickle structural change, the control in time and space is accurately carried out to material assembling, obtain structure equal
One, controllable effect is an emphasis and difficult point in self-assembling polypeptide field.
The content of the invention：
For above-mentioned technical problem of the prior art, formed using stapler self-assembling polypeptide the invention provides one kind
The method of nanotube, the method that described this utilization stapler self-assembling polypeptide forms nanotube will solve to adopt in the prior art
The method for preparing nanotube with the method for biology is difficult, the technical problem of the Character instability of nanotube.
The invention provides a kind of method that utilization stapler self-assembling polypeptide forms nanotube, it is characterised in that including such as
Lower step：
1) the step of alpha-non-natural amino acid of 2 carbon R chiralitys of a side chain for synthesis-Fmoc protections, described-Fmoc is protected
The structural formula of 2 alpha-non-natural amino acids of carbon R chiralitys of side chain of shield is as follows,Wherein X is
2) using the method for solid-phase synthetic peptide by step 1) alpha-non-natural amino acid be connected with resin, then proceed to connect
3 amino acid, described amino acid is arbitrary natural amino acid, then connects cysteine, and by the aminoterminal of cysteine
Closed with acetyl group；
3) by step 2) product removal cysteine sulfydryl on protection group, then obtained by intramolecular sulfydryl-alkene reaction
2 polypeptide compounds of carbon chiral zinc porphyrin of side chain are obtained, the position of the carbon chiral side chain coupling amino acid is i/i+4；
4) polypeptide is shear off from resin, is purified with high performance liquid chromatography；
5) polypeptide sample after purification is freezed on freeze dryer, obtains white powdery solids；
6) polypeptide sample of white powder is disperseed with ultra-pure water, is placed in ultrasound in Ultrasound Instrument, obtain many of self assembly
Peptide nanotube.
Further, step 2), step 3) and step 4) reaction equation it is as follows：
Wherein, Y1、Y2、Y3、Y4Selected from any one natural amino acid or the alpha-non-natural amino acid by modification
Side chain, X is
The elementary cell polypeptide that the present invention forms nanotube is, with the polypeptide for stablizing helical structure, to use the stapler of stabilization
Used as monomer, by the regulation and control of peptide side chain accurately chiral centre, synthesize side chain by solid phase synthesis process has machine polypeptide
γ pentapeptide of R type chiral centres of carbon teminal alpha-non-natural amino acid, (2mg/ml) is disperseed by polypeptide with ultra-pure water, is placed in Ultrasound Instrument
Ultrasound 10 minutes, has simply efficiently obtained the peptide Nanotubes that size is homogeneous, structure is special, and the peptide Nanotubes of solution can
So that further by freezing, the mode such as volatilization removes solvent in air, obtains required peptide Nanotubes solid powder.
The present invention is compared with prior art, and its technological progress is significant.The present invention is by the use of stapler polypeptide as basic
Material, is simply and efficiently prepared for the tubulose compound with nanometer property, and the novel polypeptide nanotube for preparing is in material
Learn, the aspect such as biomedicine has a wide range of applications.
Brief description of the drawings：
Fig. 1 is the flow chart that utilization stapler self-assembling polypeptide of the invention forms nanotube.
Fig. 2 is the polypeptide that obtains of embodiment 1 shape appearance figure under a scanning electron microscope.
Fig. 3 is shape appearance figure of the polypeptide that obtains of embodiment 1 under transmission electron microscope.A, B are respectively to be put in different
The surface topography of peptide Nanotubes under big multiple.
Fig. 4 is that the polypeptide that the polypeptide that obtains of embodiment 1 shape appearance figure (A) under an atomic force microscope and measurement are obtained is high
Degree figure (B).
Fig. 5 is the grain size distribution that the polypeptide that embodiment 1 is obtained is obtained through dynamic light scattering measurement.
Fig. 6 is the IR Characterization data of the peptide Nanotubes that embodiment 1 is obtained.A, B are illustrated respectively in different wavenumber regions
The INFRARED ABSORPTION of peptide Nanotubes.
Fig. 7 is the Raman spectrum data of the peptide Nanotubes that embodiment 1 is obtained.
Fig. 8 is the solid powder diffraction data of the peptide Nanotubes that embodiment 1 is obtained.
Fig. 9 is the Mass Spectrometric Identification data of the polypeptide nano material that embodiment 1 is obtained.
Figure 10 is the circular dichroism spectra data of the peptide Nanotubes that embodiment 1 is obtained.
Specific embodiment：
The invention provides a kind of method that utilization stapler self-assembling polypeptide forms nanotube, comprise the following steps：
2 alpha-non-natural amino acids of carbon R chiralitys of side chain of (I) synthesis-Fmoc protections；Structural formula is as follows：Wherein X is phenyl ring or group as follows；
Be connected to alpha-non-natural amino acid on resin with the method for solid-phase synthetic peptide by (II), continues to connect 3 amino acid
Cysteine is connected again and the aminoterminal of polypeptide is closed with acetyl group；
Acetylation closed reagent is by acetic anhydride, N, N- diisopropylethylamine (DIEA), 1-METHYLPYRROLIDONE (NMP) group
Into, acetic anhydride, the mass percent of DIPEA (DIEA) 1-METHYLPYRROLIDONE (NMP) be respectively 4.25%,
15.75%th, 80%；
(III) is by the protection group of sulfydryl on the product removal cysteine of step (II) then anti-by intramolecular sulfydryl-alkene
2 polypeptide compounds of carbon chiral zinc porphyrin of side chain should be obtained, the position of the carbon chiral side chain coupling amino acid is i/i+4；Reaction
Process is as follows：
Wherein X is phenyl ring or group as follows, Y1、Y2、Y3、Y4Including 20 kinds of natural amino acids or by modification
Alpha-non-natural amino acid side chain.
The reagent of sulfhydryl protected base is by trifluoroacetic acid (TFA), tri isopropyl silane (TIS) and (two on removing cysteine
Chloromethanes) composition, the mass percent of trifluoroacetic acid (TFA) is 3%, and the mass percent of tri isopropyl silane (TIS) is
The mass percent of 5%, DCM (dichloromethane) is 92%.
Intramolecular sulfydryl-alkene reaction condition is：Acetanisole (MAP) (1.0eq), 2- hydroxyls -4'- (2- hydroxyl second
Epoxide) -2- methyl phenyl ketones (MNP) (1.0eq), with anhydrous dimethyl formamide (DMF) be solvent in ultraviolet light 365nm conditions
Lower reaction 3h.
(IV) shear offs polypeptide from resin, is purified with high performance liquid chromatography.
V () freezes polypeptide sample after purification on freeze dryer, obtain white powdery solids.
(vi) polypeptide sample of white powder is disperseed into (2mg/ml) with ultra-pure water, is placed in 10 points of ultrasound in Ultrasound Instrument
Clock, obtains the peptide Nanotubes of self assembly.
The present invention using stabilization stapler polypeptide obtained in novel polypeptide nanotube there is specific structure and potential
Application in terms of biomedical and nano photoelectric, scanned electron microscope (SEM), transmission electron microscope (TEM), atom
Force microscope (AFM), infrared spectrum (FTIR), Raman spectrum (Raman), solid powder diffractive technology (XRD) and dynamic optical
Scattering (DLS) characterization technique, detailed sign has been carried out to nano tube structure.
Embodiment 1
The invention provides stapler cyclic peptide Ac-cyclo (1,5)-CAAAS5(2-phenyl)-NH2What is be self-assembly of is more
The preparation method of peptide nanotube,
The alpha-non-natural amino acid S of R configurations Fmoc protections5The structural formula of (2-phenyl) is：
First it is to synthesize NH with Fmoc solid phase polypeptide synthesis2-CAAAS5(2-phenyl)-mbha resin, specific route is such as
Under：
Concrete operations are：
1. first amino acid is connect：1.0g mbha resins are weighed in 100ml connects peptide pipe, 20ml N- methylpyrroles are added
The swelling 30min of alkanone (NMP) drum nitrogen；The nmp solution that solvent adds volume ratio to be 25% morpholine is filtered, nitrogen 30min is roused,
Washing；Coupled reaction：Addition Fmoc-S5 (2-phenyl)-OH (0.4M in NMP) solution, HCUT (0.38M in NMP),
DIEA presses 5.0ml/5.0ml/0.71ml and mixes drum nitrogen 120min in addition resin, filters reaction solution.Washing：In connecing peptide pipe
Solvent drain, resin is washed three times, every time one minute with NMP (10ml*3)；
2. second amino acid is connect：Deprotection：The nmp solution that volume ratio is 25% morpholine is added, nitrogen 30min is roused,
Washing；Coupled reaction：Fmoc-Ala-OH (the 0.4M in NMP) solution, 6- Chloro-Benzotriazole -1,1,3,3- that will be prepared
Tetramethylurea hexafluorophosphoric acid ester (HCUT) (0.38M in NMP), DIEA presses 7.5ml/7.5ml/1ml and mixes drum in addition resin
Nitrogen 50min；Reaction solution is filtered, then washing carries out next step operation.
3. the 3rd amino acid is connect：Operation meets the 3rd Ala with 2.
4. the 4th amino acid is connect：Operation meets the 4th Ala with 2.Deprotection：It is 25% morpholine to add volume ratio
Nmp solution, drum nitrogen 30min, washs 3 times.
5. five amino acid Cys is met：Deprotection：Add the nmp solution that volume ratio is 25% morpholine, drum nitrogen
30min, washing；Coupled reaction：Fmoc-Cys (Trt)-OH (the 0.4M in NMP) solution that will be prepared, 6- chlorobenzenes and three nitrogen
Azoles -1,1,3,3- tetramethylurea hexafluorophosphoric acids ester (HCUT) (0.38M in NMP), DIEA presses 7.5ml/7.5ml/1ml and mixes and adds
Enter drum nitrogen 50min in resin；Reaction solution is filtered, then washing carries out next step operation.
The acetylation closing of 6.N ends：Deprotection：The nmp solution that volume ratio is 25% morpholine, drum nitrogen 30min is added to wash
Wash；N-terminal acetylation is closed：Acetylation closed reagent (the acetic anhydride that will be prepared：DIEA：NMP=4.25%：15.7%：80%)
Mix and add drum nitrogen 120min in resin；Reaction solution is filtered, then washing carries out next step operation.
7.-Trt the protection groups of sulfydryl on cysteine are removed：Removing-Trt the groups that will be prepared reagent (3%TFA,
5%TIS and 92%DCM) mix and add in resin after drum nitrogen 20min, reaction solution is filtered, wash, removing-Trt is added again
The reagent drum nitrogen 20min of group, filters reaction solution, washs, and then carries out next step operation.
8. reaction solution is filtered, resin is used into NMP (10ml), dichloromethane (DCM) (10ml), methyl alcohol (MeOH) successively
(10ml) is alternately washed, and drains preservation or for next step reaction.
(sulfydryl-alkene reaction) is reacted by thiol-ene to complete side chain structure.
Concrete operations are：Weigh 1.0g AcHN-CAAAS5(2-phenyl)-mbha resin in 100ml flasks, successively
Add 70mg MAP, 105mg MNP and 50ml DMF；The oxygen removed in solvent for three times with argon gas ventilation；The flask is placed in light
Lower reaction 3h is stirred in reactor；Then reacting resin is transferred in connecing peptide pipe, reaction solution is filtered, with DMF (10ml), DCM
(10ml), alternately washs, and drains to obtain Ac-cyclo (1,5)-CAAAS5(2-phenyl)-NH2Resin.
Use shearing liquid (trifluoroacetic acid:Tri isopropyl silane:Water=95：2.5：2.5) under polypeptide being sheared from resin
Come, filter resin, use N2The drying of shearing liquid, with (the ether of cooling：N-hexane=1：1) precipitate, precipitation adds water molten with acetonitrile
Purified with HPLC after solution, 460nm*2.5mm C18 reverse-phase chromatographies, A liquid：0.1% trifluoroacetic acid/water, B liquid：0.1% trifluoro second
Acid/acetonitrile；Solvent Gradient：0-10min 5-15%；10-30min 15-55%；Rt=26.00min.As for jelly after MS detections
Freezed on dry machine, obtain white powdery solids, its structural formula is：
Molecular formula is：C27H40N6O6S。
9. the polypeptide sample of lyophilized white powder is disperseed into (2mg/ml) with ultra-pure water, be placed in ultrasound 10 in Ultrasound Instrument
Minute, obtain the peptide Nanotubes of self assembly.
10. polypeptide is suctioned out, be equably applied on silicon chip, be placed in the environment of well-ventilated, treat that solvent is evaporated completely
Finish, peptide Nanotubes form equably film layer on silicon chip.
11. carry out table using SEM or techniques mentioned above means to the pattern of peptide Nanotubes
Levy.
Embodiment 1 obtains preparation and the characterize data of peptide Nanotubes：
The preparation flow figure of peptide Nanotubes is as shown in Figure 1.Fig. 2 is peptide Nanotubes below Scanning Electron microscope
Pattern, peptide Nanotubes are square tubular structure.Further by transmission electron microscope (as shown in Figure 3), and atom
Force microscope is characterized to the structure of polypeptide.(as shown in Figure 4) is can be seen that from the analysis of AFM, polypeptide
It is highly 200nm or so, width is about 1-2um, and length is 10-100um.(as shown in Figure 4), dynamic light scattering has obtained polypeptide
Particle diameter distribution, it is illustrated that indicate polypeptide the aqueous solution average grain diameter be 1um (as shown in Figure 5).Fig. 6 is what embodiment 1 was obtained
The IR Characterization data of peptide Nanotubes.Show that polypeptide is helical structure (A) in the strong INFRARED ABSORPTIONs of 1654cm-1.
Absworption peak at 3266cm-1 and 3319cm-1 is indicated strong hydrogen bond network (B) inside polypeptide pipe.Fig. 7 is embodiment 1
The Raman spectrum data of the peptide Nanotubes for obtaining, as illustrated, polypeptide nano material has very strong Raman to inhale in 1652cm-1
Receive, further illustrate polypeptide for helical structure.Fig. 8 is the solid powder diffraction data of the peptide Nanotubes that embodiment 1 is obtained, and is led to
The figure is crossed, illustrates that peptide Nanotubes have very regular internal structure.Fig. 9 is the circular dichroism spectra of the polypeptide that embodiment 1 is obtained
Data.As illustrated, there is stronger absorption at 205nm and 220nm, display polypeptide is helical structure.Figure 10 is embodiment 1
The Mass Spectrometric Identification data of the polypeptide nano material for obtaining.Mass spectrometric data shows that the molecular weight of polypeptide is 576g/mol.Show its point
Minor is：C27H40N6O6S。
The above, only presently preferred embodiments of the present invention, it is not any to the present invention in form and substantial limitation,
It should be pointed out that for one of ordinary skill in the art, on the premise of the inventive method is not departed from, can also make some
Improve and supplement, these are improved and supplement also should be regarded as protection scope of the present invention.All those skilled in the art, not
Depart from the spirit and scope of the present invention in the case of, when a little change made using disclosed above technology contents,
Modification and the equivalent variations for developing, are Equivalent embodiments of the invention；Meanwhile, it is all according to substantial technological of the invention to above-mentioned
The variation, modification and evolution of any equivalent variations that embodiment is made, still fall within the range of technical scheme.
Claims (2)
1. a kind of method that utilization stapler self-assembling polypeptide forms nanotube, it is characterised in that comprise the following steps：
1) the step of alpha-non-natural amino acid of 2 carbon R chiralitys of a side chain for synthesis-Fmoc protections, what described-Fmoc was protected
The structural formula of 2 carbon R of side chain chiral alpha-non-natural amino acid is as follows,
Wherein X isOrOrOrOrOrOrOrOrOrOrOrOrOrOrOr
2) using the method for solid-phase synthetic peptide by step 1) alpha-non-natural amino acid be connected with resin, then proceed to connect 3
Amino acid, described amino acid is arbitrary natural amino acid, then connects cysteine, and by the aminoterminal second of cysteine
Acyl group is closed；
3) by step 2) product removal cysteine sulfydryl on protection group, then obtain side by intramolecular sulfydryl-alkene reaction
2 polypeptide compounds of carbon chiral zinc porphyrin of chain, the position of the carbon chiral side chain coupling amino acid is i/i+4；
4) polypeptide is shear off from resin, is purified with high performance liquid chromatography；
5) polypeptide sample after purification is freezed on freeze dryer, obtains white powdery solids；
6) polypeptide sample of white powder is disperseed with ultra-pure water, is placed in ultrasound in Ultrasound Instrument, the polypeptide for obtaining self assembly is received
Mitron.
2. the method that a kind of utilization stapler self-assembling polypeptide according to claim 1 forms nanotube, it is characterised in that
Step 2), step 3) and step 4) reaction equation it is as follows：
Wherein, Y1、Y2、Y3、Y4Selected from any one natural amino acid or the side chain of the alpha-non-natural amino acid for passing through modification, X isOrOrOrOrOrOrOrOrOrOrOrOrOrOrOr
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112245593A (en) * | 2020-10-30 | 2021-01-22 | 西南交通大学 | Stabilized cell penetrating peptide with hydrophobic side chain, preparation method and application |
| CN114456229A (en) * | 2021-12-16 | 2022-05-10 | 北京大学深圳研究生院 | S-configuration cyclic pentapeptide, self-assembly material thereof and preparation method |
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| CN101917959A (en) * | 2006-12-01 | 2010-12-15 | 安特里奥公司 | Peptide nanoparticles and uses therefor |
| CN103608354A (en) * | 2011-04-25 | 2014-02-26 | 大鹏药品工业株式会社 | Nanoparticles containing pH-responsive peptide |
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| CN101917959A (en) * | 2006-12-01 | 2010-12-15 | 安特里奥公司 | Peptide nanoparticles and uses therefor |
| CN103608354A (en) * | 2011-04-25 | 2014-02-26 | 大鹏药品工业株式会社 | Nanoparticles containing pH-responsive peptide |
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| YUAN TIAN等: ""Stapling of unprotected helical peptides via photoinduced intramolecular thiol–yne hydrothiolation"", 《CHEMICAL SCIENCE》 * |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112245593A (en) * | 2020-10-30 | 2021-01-22 | 西南交通大学 | Stabilized cell penetrating peptide with hydrophobic side chain, preparation method and application |
| CN114456229A (en) * | 2021-12-16 | 2022-05-10 | 北京大学深圳研究生院 | S-configuration cyclic pentapeptide, self-assembly material thereof and preparation method |
| CN114456229B (en) * | 2021-12-16 | 2023-09-01 | 北京大学深圳研究生院 | S-configuration cyclic pentapeptide, self-assembly material and preparation method thereof |
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