CN108359018B - A kind of modified cellulose and its preparation method and application of Rink Amide linker modification - Google Patents
A kind of modified cellulose and its preparation method and application of Rink Amide linker modification Download PDFInfo
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- CN108359018B CN108359018B CN201810350887.5A CN201810350887A CN108359018B CN 108359018 B CN108359018 B CN 108359018B CN 201810350887 A CN201810350887 A CN 201810350887A CN 108359018 B CN108359018 B CN 108359018B
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- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
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- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
- C07K1/042—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers characterised by the nature of the carrier
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Abstract
The present invention relates to a kind of modified celluloses and its preparation method and application of Rink Amide linker modification.One kind modified cellulose as shown in formula (I), the modified cellulose are modified to obtain after replacing the sugared hydroxyl in the position 6- in the cellulose as shown in formula (III) by the long-chain compound as shown in formula (II), , wherein n is 2 ~ 7.The present invention carries out substituting modification to cellulose by the long-chain compound with Amino End Group, and it is modified using Rink Amide linker so that modified cellulose has long chain space and more preferably reactivity, it can preferably realize manually and automatically solid state polypeptide synthesis, yield is high, condition is simple, at low cost；In addition the scanning for carrying out polypeptide active can not be cut after solid state polypeptide synthesis, the polypeptide synthesized after scanning can be cut from matrix, be carried out further synthesizing identification or quantitative analysis with mass spectrum.
Description
Technical field
The invention belongs to Peptide systhesis matrix fields, and in particular to a kind of improvement of Rink Amide linker modification is fine
Tie up element and its preparation method and application.
Background technique
Polypeptide is to be related to the bioactive substance of various cell functions in organism.It is molecular structure between amino acid and
A kind of compound between protein is formed according to certain putting in order by peptide linkage by a variety of amino acid.It is now right
In the research and utilization of polypeptide, there is a unprecedented prosperity scene.The chemical synthesising technology of polypeptide either liquid phase method is also
It is that solid phase method is all mature.Pass through the fully synthetic structure that can verify a new polypeptide of polypeptide；New polypeptide is designed, can be used for
The relationship of research structure and function provides important information for polypeptide biosynthesis reaction mechanism, establishes model enzyme and synthesis is new
Polypeptide drugs etc..The fully synthetic of polypeptide not only has critically important theory significance, but also has important application value.
By continuous improve and perfect, solid phase method has become a common technology in peptide and protein synthesis, table
The incomparable advantage of classical liquid phase synthesizing method is revealed.Such as: Solid phase synthesis polypeptide more with its time saving, laborsaving, material-saving, be convenient for
Computer control, outstanding advantage easy to popularize and become Peptide systhesis conventional method.Solid-phase synthetic peptide synthesis
Basic principle is the process that amino acid is added in a repetition, synthesis from the end C (c-terminus) to N-terminal (aminoterminal) synthesis: first by institute
It synthesizes the hydroxyl of the hydroxyl end amino acid of peptide chain to be connected with the same insoluble macromolecule linker of the structure of covalent bond, so
The amino acid on solid phase carrier is incorporated in as moiety by sloughing amino protecting group and with excessive activation carboxylic using this afterwards
Base component reaction, spreading peptide chain.(condensation → washing → deprotection → neutralization and washing → next round condensation) operation is repeated, is reached
Peptide chain is finally cleaved by the peptide chain length to be synthesized from resin, by the processing such as purifying to get desired polypeptide.
Wherein alpha-amido BOC(tertbutyloxycarbonyl) protection be known as BOC solid-phase synthesis, alpha-amido FMOC(9- fluorenes methoxy carbonyl
Base) protection be known as FMOC solid-phase synthesis.
But a large amount of polypeptide is synthesized, Chemical Screening such as, which is carried out, using polypeptide chain identifies polygamy body protein affinity reagent,
Establishing the standard Solid phase peptide synthssis technology on macromolecule resin seems slow and expensive；Because of polypeptide needed for Chemical Screening
Quality is small, but enormous amount.In recent years, Solid phase peptide synthssis traditional resin (such as Wanglinker and
Rinkerlinker in principle), several different modifying matrix has been developed and have carried out Peptide systhesis.It is synthesized including tealeaves
(tea-bag), digital photolithography, needle (pin) synthesis and SPOT synthesis on cellulose.These improved technologies are with highly effective
Mode using standard peptide synthesis of chemicals and building module, and avoid the purifying and analysis of peptide.With standard solid-phase polypeptide
Synthesis is compared, and the cost of SPOT Peptide systhesis sharply declines.SPOT synthesis wherein on cellulose is easily operated, can hold manually
Row, also can be used semi-automatic or full-automatic machine people, the quality and quantity of peptide can be modified freely, peptide-ligand phase interaction
Detection is easy to operate.SPOT method follows standard Fmoc chemistry, based on the Solid phase peptide synthesis on cellulose filter disc.Fiber
The use of element itself has the advantages that several compared with other materials: it is cheap and is resistant to have used in peptide synthesis process
Solvent and acid.In addition, cellulose is stable in aqueous solution, because it is nontoxic, suitable screening biological sample,
Although optimum range is between 6 to 18 amino acid.
Because of the polysaccharide that cellulose is made of the hundreds of D-Glucose units connected to tens of thousands of a β (1 → 4) of straight line chain,
Its sugared hydroxyl (- OH) and short chain space lead to the directly stringent and low yield using it as the Solid phase peptide synthssis condition of matrix.
Therefore, it develops a kind of modified cellulose and makes Solid phase peptide synthssis anti-as the matrix of solid state polypeptide synthetic reaction
Product yield is high and is easy to carry out the research significance and promotional value that have important.
Summary of the invention
Condition is harsh when it is an object of the invention to overcome matrix of the existing cellulose as solid state polypeptide synthetic reaction, produces
The low defect of rate provides a kind of modified cellulose of Rink Amide linker modification.Modified cellulose benefit provided by the invention
Long-chain with end with amino replaces sugared hydroxyl, overcomes the problem of sugared hydroxyl and short chain space are brought in cellulose, can reduce
SPOT Solid phase peptide synthssis condition improves yield, greatly reduces Solid phase peptide synthssis cost；In addition Rink Amide is recycled
Linker is modified, and using the cellulose that this is modified as the Solid phase peptide synthssis of matrix, not cutting can be used as polypeptide active
It scans (bioactive peptide screening)；After activity scanning simultaneously, the polypeptide of synthesis can be from Rink Amide
It is cut in the matrix of linkerlinker, is carried out further synthesizing identification or quantitative analysis with mass spectrum.Although Rink
The end C- of polypeptide under Amide linker cutting is amide (- CONH2), and really with carboxylic acid group (- COOH) for C- end
The polypeptide (such as Wang linker) of synthesis has the difference of 1Da；But the reactivity of Rink Amide linker is stronger, yield
It is higher, the purity is high of reaction product.
Another object of the present invention is to provide the preparation methods of above-mentioned modified cellulose.
Application another object of the present invention is to provide above-mentioned modified cellulose as matrix in solid state polypeptide synthesis.
For achieving the above object, the present invention adopts the following technical scheme:
The modified cellulose of one kind Rink Amidelinker as shown in formula (I) modification, the modified cellulose is by such as
Long-chain compound shown in formula (II) containing Amino End Group carries out after replacing the sugared hydroxyl in the position 6- in the cellulose as shown in formula (III)
Rink Amide linker modifies to obtain,
,
Wherein, n is 2 ~ 7.
The present inventor attempts through long-chain compound come the short chain space of increased fiber element to improve cellulose
Performance, the functional group of long-chain compound and the selection of chain length are key factors.Through repeatedly the study found that when holding functional group both ends all
When for amino, an aminoterminal replaces the sugared hydroxyl of cellulose, realizes the connection of long-chain；Another amino is in long-chain
End provides the space with the synthesis of the hydroxyl of amino acid, while also realizing the same reaction conditions of homopolypeptide synthesis, makes automatic more
Peptide synthesis is easier to carry out；On the other hand, when the simple degree and multiplicity of the repetitive structure for choosing long-chain compound are to performance
Improvement it is also extremely important, when chain length too short (such as n=1) limit polypeptide length；As chain length is too long (as (n > 7) cause polypeptide to close
At low yield.On the other hand, it is further modified using Rink Amide linker, using the cellulose that this is modified as base
The Solid phase peptide synthssis of matter can be used as scanning (the bioactive peptide for carrying out polypeptide active without cutting
Screening)；After activity scanning simultaneously, the polypeptide of synthesis can be cut from Rink Amide linker matrix, use matter
Spectrum carries out further synthesis identification or quantitative analysis.
Therefore the modified cellulose of Rink Amide linker modification provided by the invention passes through with the long of Amino End Group
Object is closed to carry out Rink Amide linker modification after replacing to cellulose, so that cellulose has long chain space
More preferably reactivity can be used as matrix and preferably realize manually and automatically solid state polypeptide synthesis, and yield is high, and condition is easy.
Preferably, the cellulose is paper fiber element.
It is further preferable that the cellulose is filter paper.
Preferably, 3 n.
The present invention provides a kind of preparation method of above-mentioned modified cellulose, and described method includes following steps:
S1: the pyridine solution of cellulose and paratoluensulfonyl chloride is mixed, and oscillation air-dries after washing；
S2: being added long-chain compound shown in formula (II), after being vibrated to fully reacting, washs, air-dries；
S3: Rink Amide linker and activator is added and is dissolved in solvent, is washed after reaction up to the improvement
Cellulose.
Preferably, in the pyridine solution of paratoluensulfonyl chloride described in S1 paratoluensulfonyl chloride mass concentration be 350 ~
400g/L。
It is further preferable that the mass concentration of toluene sulfochloride is 380g/ in the pyridine solution of paratoluensulfonyl chloride described in S1
L。
Preferably, activator described in S3 be HOBt hydroxybenzotriazole and DIC N, N '-diisopropyl carbon imines, or
For HOSu n-hydroxysuccinimide and DIC N, N '-diisopropyl carbon imines；The temperature of the reaction is 50 ~ 80 DEG C, instead
It is 10 ~ 40 min between seasonable.
It is further preferable that the temperature of the reaction is 70 DEG C, the time of reaction is 15min.
Preferably, further include the steps that carrying out Non-aqueous processing to cellulose before S1 step.
Preferably, the solvent washed in S2 is dimethylformamide and methylene chloride.
Preferably, solvent is DMF in S3.
Above-mentioned modified cellulose is also within the scope of the present invention as application of the matrix in solid state polypeptide synthesis.
Compared with prior art, the invention has the following beneficial effects:
The modified cellulose of Rink Amide linker modification provided by the invention passes through the long-chain chemical combination with Amino End Group
Object carries out Rink Amide linker modification after replacing to cellulose so that cellulose have long chain space and
More preferably reactivity can be used as matrix and preferably realize manually and automatically solid state polypeptide synthesis, and yield is high, and condition is easy, drop
Low synthesis cost.It is further modified using Rink Amide linker, using the cellulose that this is modified as the solid phase of matrix
Peptide systhesis does not cut the scanning (bioactive peptide screening) that can carry out polypeptide active；Activity scanning simultaneously
Afterwards, the polypeptide of synthesis can be cut from Rink Amide linker matrix, be carried out further synthesizing identification with mass spectrum,
Or quantitative analysis.
Detailed description of the invention
Fig. 1 is the sugared structure of paper fiber element；
Fig. 2 is the modified cellulose and its preparation process signal for the Rink Amide linker modification that embodiment 1 provides
Figure；
Fig. 3 is Solid phase peptide synthssis step schematic diagram；
Fig. 4 is liquid chromatography-mass spectrography detection synthesis polypeptide (valine-valine-valine-valine-lysine)
Result figure.
Specific embodiment
Below with reference to embodiment, the present invention is further explained.These embodiments are merely to illustrate the present invention rather than limitation
The scope of the present invention.Test method without specific conditions in lower example embodiment usually according to this field normal condition or is pressed
The condition suggested according to manufacturer；Used raw material, reagent etc., unless otherwise specified, being can be from the business such as conventional market
The raw materials and reagents that approach obtains.The variation for any unsubstantiality that those skilled in the art is done on the basis of the present invention
And replacement belongs to scope of the present invention.
Embodiment 1
The present embodiment provides a kind of modified cellulose of Rink Amide linker modification, structural formula is as follows:
。
Such as Fig. 2, modified cellulose provided in this embodiment is prepared by the following procedure method and is prepared:
(1) the laboratory filter paper (Whatman 50, structural formula such as Fig. 1) of certain size is got out, stainless steel is put into
In container, enough dimethylformamides (DMF) (washing step) is added into rustless steel container, gently concussion 1 hour, then
Pour into solvent (being repeated 3 times)；Then enough methylene chloride (DCM) are added into rustless steel container, gently concussion 10 minutes, so
After pour into solvent (being repeated 3 times), air-dry；
(2) air-dried papery cellulose membrane is placed in rustless steel container, is added into rustless steel container enough to toluene sulphur
The pyridine solution (380g toluene sulfochloride is dissolved in 1 L pyridine) of acyl chlorides gently shakes 15 minutes, at room temperature to rustless steel container
It is middle that enough DMF(washing steps are added), it gently shakes 20 minutes, is subsequently poured into solvent (being repeated 3 times)；Enough DCM are added not
It becomes rusty in steel container, gently shakes 10 minutes, be subsequently poured into solvent (being repeated 3 times), air-dry papery cellulose；
(3) air-dried papery cellulose membrane is placed in rustless steel container, enough 4,7,10 three oxygen -1,13- 13 is added
Alkane diamines (TTDDA) gently shakes overnight at room temperature；Enough dimethylformamides (DMF) is added into rustless steel container
(washing step) gently shakes 1 hour, is subsequently poured into solvent (being repeated 3 times)；Enough methylene chloride (DCM) is added to stainless steel
It in container, gently shakes 10 minutes, is subsequently poured into solvent (being repeated 3 times), air-dry；
(4) the paper fiber element after air-drying step (3) is placed in rustless steel container, and 0.7mol Rink Amide is added
Linker(structural formula are as follows:), 0.7mol hydroxybenzotriazole (HOBt), 0.7mol
N, N '-diisopropyl carbon imines DIC and solvent DMF shake 15 minutes at 70 DEG C, then successively use DMF, ethyl alcohol (2 times) and DCM
Washing air-dries to obtain the final product.
Embodiment 2
The present embodiment provides a kind of modified cellulose, structural formula is as follows:
。
Modified cellulose provided by the invention is prepared by the following procedure method and is prepared:
(1) the laboratory filter paper (Whatman 50) of certain size is got out, is put into rustless steel container, to stainless steel
Enough dimethylformamides (DMF) (washing step) is added in container, gently shakes 1 hour, is subsequently poured into solvent and (repeats 3
It is secondary)；Then enough methylene chloride (DCM) are added into rustless steel container, gently shake 10 minutes, is subsequently poured into solvent and (repeats
3 times), it air-dries；
(2) air-dried papery cellulose membrane is placed in rustless steel container, is added into rustless steel container enough to toluene sulphur
The pyridine solution (350g toluene sulfochloride is dissolved in 1 L pyridine) of acyl chlorides gently shakes 15 minutes, at room temperature to rustless steel container
It is middle that enough DMF(washing steps are added), it gently shakes 20 minutes, is subsequently poured into solvent (being repeated 3 times)；Enough DCM are added not
It becomes rusty in steel container, gently shakes 10 minutes, be subsequently poured into solvent (being repeated 3 times), air-dry papery cellulose；
(3) air-dried papery cellulose membrane is placed in rustless steel container, enough bis- (3- amino propoxyl group) ethane is added
(Bis (3-Aminopropoxy) ethane) gently shakes overnight at room temperature；Enough diformazans are added into rustless steel container
Base formamide (DMF) (washing step) gently shakes 1 hour, is subsequently poured into solvent (being repeated 3 times)；Enough methylene chloride are added
(DCM) it into rustless steel container, gently shakes 10 minutes, is subsequently poured into solvent (being repeated 3 times), air-dry；
(4) the paper fiber element after air-drying step (3) is placed in rustless steel container, and 0.7mol Rink Amide is added
Linker(structural formula are as follows:), 0.7mol hydroxybenzotriazole (HOBt), 0.7mol N,
N '-diisopropyl carbon imines DIC and solvent DMF, 50 DEG C gently shake 40 minutes, then successively with DMF, ethyl alcohol (2 times) and
DCM washing, air-dries to obtain the final product.
Embodiment 3
The present embodiment provides a kind of modified cellulose, structural formula is as follows:
。
Modified cellulose provided by the invention is prepared by the following procedure method and is prepared:
(1) the laboratory filter paper (Whatman 50) of certain size is got out, is put into rustless steel container, to stainless steel
Enough dimethylformamides (DMF) (washing step) is added in container, gently shakes 1 hour, is subsequently poured into solvent and (repeats 3
It is secondary)；Then enough methylene chloride (DCM) are added into rustless steel container, gently shake 10 minutes, is subsequently poured into solvent and (repeats
3 times), it air-dries；
(2) air-dried papery cellulose membrane is placed in rustless steel container, is added into rustless steel container enough to toluene sulphur
The pyridine solution (400gg toluene sulfochloride is dissolved in 1 L pyridine) of acyl chlorides gently shakes 15 minutes, at room temperature to rustless steel container
It is middle that enough DMF(washing steps are added), it gently shakes 20 minutes, is subsequently poured into solvent (being repeated 3 times)；Enough DCM are added not
It becomes rusty in steel container, gently shakes 10 minutes, be subsequently poured into solvent (being repeated 3 times), air-dry papery cellulose；
(3) air-dried papery cellulose membrane is placed in rustless steel container, bis- (3- ammonia third in enough heptan (ethylene glycol) is added
Base) (Hepta (ethylene glycol) bis (3-aminopropyl) gently shakes overnight at room temperature；Hold to stainless steel
Enough dimethylformamides (DMF) (washing step) is added in device, gently shakes 1 hour, is subsequently poured into solvent and (repeats 3
It is secondary)；Enough methylene chloride (DCM) are added into rustless steel container, gently shake 10 minutes, is subsequently poured into solvent and (repeats 3
It is secondary), it air-dries；
(4) the paper fiber element after air-drying step (3) is placed in rustless steel container, and 0.7mol Rink Amide is added
Linker(structural formula are as follows:), 0.7mol hydroxybenzotriazole (HOBt), 0.7mol N,
N '-diisopropyl carbon imines DIC and solvent DMF are shaken 10 minutes at 80 DEG C, are then successively washed with DMF, ethyl alcohol (2 times) and DCM
It washs, air-dries to obtain the final product.
Application examples
By taking the modified cellulose for the Rink Amide linker modification that embodiment 1 provides as an example, the modified cellulose is tested
Performance.
The modified cellulose of the Rink Amide linker modification provided using embodiment 1 carries out solid state polypeptide conjunction as matrix
At, and the polypeptide of synthesis is tested.Step has: blocking group and Rink Amide are cut in automatic synthesizer synthesis
It is cut in the modified cellulose of linker modification, mass spectral analysis composite result.
It is synthesized from C-terminal to N-terminal using Peptide synthesizer.The schematic process of synthesis is as shown in Figure 3.With automatic synthesizer
Synthesis polypeptide valine-valine-valine-valine-lysine (Ver-Ver-Ver-Ver-Lys) for: first use DMF
With the modified cellulose of ethanol wet and cleaning Rink Amide linker modification, Fmoc is gone to protect with pyridine solution, the first step
C-terminal amino acid -- lysine (Lys) is added in synthesis, then repeats deprotection and synthesis step, until polypeptide needed for synthesis；Finally
It is deprotected with pyridine.It is cut out polypeptide (such as Ver-Ver- synthesized in the modified cellulose of Rink Amide linker modification
Ver-Ver-Lys), the cutting of every SPOT polypeptide 90% trifluoroacetic acid of 100ul, 3% tri isopropyl silane, 2% water and
5% methylene chloride gently shakes 2 hours.
The polypeptide (valine-valine-valine-valine-lysine) synthesized with liquid chromatography-mass spectrography detection,
Molecular weight is 541.3, main compound is shown as in liquid chromatography-mass spectrography figure (Fig. 4) in retention time at 8.64 minutes,
Proton ion peak is 542.4, for the target polypeptides of synthesis.As shown in Figure 4, polypeptide (valine-valine-figured silk fabrics is successfully synthesized
Propylhomoserin-valine-lysine), which has good performance, can be used as the matrix of solid state polypeptide synthesis, has
Good reactivity and synthesis purity.
Claims (9)
1. the modified cellulose of one kind Rink Amide linker as shown in formula (I) modification, which is characterized in that the improvement is fine
Dimension element replaces the position the 6- sugar in the cellulose as shown in formula (III) by the long-chain compound as shown in formula (II) containing Amino End Group
Rink Amide linker is carried out after hydroxyl to modify to obtain,
Wherein, n is 2 ~ 7.
2. modified cellulose according to claim 1, which is characterized in that the cellulose is paper fiber element.
3. modified cellulose according to claim 2, which is characterized in that the cellulose is filter paper.
4. modified cellulose according to claim 1, which is characterized in that n 3.
5. the preparation method of any modified cellulose of claim 1 ~ 4, which is characterized in that the method includes walking as follows
It is rapid:
S1: the pyridine solution of cellulose and paratoluensulfonyl chloride is mixed, and oscillation air-dries after washing；
S2: being added long-chain compound shown in formula (II), after being vibrated to fully reacting, washs, air-dries；
S3: Rink Amide linker and activator is added and is dissolved in solvent, is washed after reaction up to the improvement fiber
Element.
6. the preparation method of modified cellulose according to claim 5, which is characterized in that the pyrrole of paratoluensulfonyl chloride described in S1
The mass concentration of paratoluensulfonyl chloride is 350 ~ 400g/L in pyridine solution.
7. the preparation method of modified cellulose according to claim 5, which is characterized in that activator described in S3 is HOBt
Hydroxybenzotriazole and DIC N, N '-diisopropyl carbon imines, or be HOSu n-hydroxysuccinimide and DIC N, N '-two
Isopropyl carbon imines；The temperature of the reaction is 50 ~ 80 DEG C, and the reaction time is 10 ~ 40 min.
8. the preparation method of modified cellulose according to claim 7, which is characterized in that the temperature of the reaction is 70 DEG C,
Reaction time is 15 min.
9. application of any modified cellulose of claim 1 ~ 4 as matrix in solid state polypeptide synthesis.
Priority Applications (3)
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| CN201810350887.5A CN108359018B (en) | 2018-04-18 | 2018-04-18 | A kind of modified cellulose and its preparation method and application of Rink Amide linker modification |
| PCT/CN2018/095903 WO2019200764A1 (en) | 2018-04-18 | 2018-07-17 | Improved cellulose and preparation method and application therefor |
| US16/608,793 US20200308310A1 (en) | 2018-04-18 | 2018-07-17 | Novel modified cellulose, method for preparing the same and use thereof |
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| CN201810350887.5A CN108359018B (en) | 2018-04-18 | 2018-04-18 | A kind of modified cellulose and its preparation method and application of Rink Amide linker modification |
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| CN108359018B true CN108359018B (en) | 2019-07-30 |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1795202A (en) * | 2003-05-23 | 2006-06-28 | 阿普拉根有限责任公司 | Metal chelate complexes immobilized on solid supports for peptide preparation |
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| US7897724B2 (en) * | 2004-10-10 | 2011-03-01 | Usv, Ltd. | Solid phase Fmoc chemistry process to prepare peptides |
| KR101663945B1 (en) * | 2015-03-11 | 2016-10-13 | 포항공과대학교 산학협력단 | Method for preparing of RGD peptide using aspartame |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1795202A (en) * | 2003-05-23 | 2006-06-28 | 阿普拉根有限责任公司 | Metal chelate complexes immobilized on solid supports for peptide preparation |
Non-Patent Citations (1)
| Title |
|---|
| SUBPOL: A Novel Sucrose-Based Polymer Support for Solid-Phase Peptide Synthesis and Affinity Chromatography Applications;Alexander Poschalko等;《J. AM. CHEM. SOC.》;20031008;第13417页左栏第2段-第13422页左栏第2段 |
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