CN105199098A - Synthetic method of polypeptide-like compound - Google Patents
Synthetic method of polypeptide-like compound Download PDFInfo
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- CN105199098A CN105199098A CN201510763055.2A CN201510763055A CN105199098A CN 105199098 A CN105199098 A CN 105199098A CN 201510763055 A CN201510763055 A CN 201510763055A CN 105199098 A CN105199098 A CN 105199098A
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- synthetic method
- carboxylic acid
- acid
- polypeptide
- monomer
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- 238000010189 synthetic method Methods 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 title 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 43
- 238000006243 chemical reaction Methods 0.000 claims abstract description 30
- 239000000178 monomer Substances 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- 239000003999 initiator Substances 0.000 claims abstract description 13
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims abstract description 13
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 6
- 229920001184 polypeptide Polymers 0.000 claims description 23
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 23
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 7
- -1 aromatic primary amine Chemical class 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 abstract description 23
- 238000000034 method Methods 0.000 abstract description 12
- 238000009826 distribution Methods 0.000 abstract description 9
- 238000006116 polymerization reaction Methods 0.000 abstract description 6
- 150000003141 primary amines Chemical class 0.000 abstract description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract description 4
- 230000000977 initiatory effect Effects 0.000 abstract description 3
- 239000002861 polymer material Substances 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 150000003142 primary aromatic amines Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- 238000001291 vacuum drying Methods 0.000 description 7
- 230000009286 beneficial effect Effects 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000599 controlled substance Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- Polyethers (AREA)
- Polyamides (AREA)
Abstract
The invention discloses a method for synthesizing polypeptide-like substances, which belongs to the technical field of high polymer materials and is used for preparing the polypeptide-like substances by using primary alkyl amine or primary aromatic amine as an initiator and N-substituted glycine-N-carboxylic anhydride as a monomer and initiating solution ring-opening polymerization of the N-substituted glycine-N-carboxylic anhydride by the primary amine under the condition of nitrogen flow. The invention adopts the nitrogen flow mode to rapidly take out the carbon dioxide generated in the reaction process, so that the reaction rate is improved, and the polymerization reaction is favorably carried out; the polypeptide-like produced by the method has narrow molecular weight distribution and molecular weight.
Description
Technical field
The invention belongs to technical field of polymer materials, be specifically related to the synthetic method of a kind polypeptide.
Background technology
Class polypeptide is the bionical polypeptide of a class, and in recent years at controlled drug delivery system, smart coat, the fields such as bio-nanotechnology are subject to extensive concern and research.
Synthesis more existing researchs at present of class polypeptide, as early stage investigators utilize the method for progressively synthesizing to prepare class polypeptide.But with these class methods synthesize class polypeptide have some limitation as: consuming time, productive rate is low, low polymerization degree etc., and therefore these class methods are not suitable for the class polypeptide of high-polymerization degree.Afterwards, Zhang etc. deliver " CyclicPoly (α-peptoid) sandTheirBlockCopolymersfromN-HeterocyclicCarbene-Mediat edRing-OpeningPolymerizationsofN-SubstitutedN-Carboxylan hydrides " (N-heterocyclic carbine causes the ring-opening polymerization of N-replacement-N-carboxylic acid and prepares ring-like polypeptide and their segmented copolymer) at " JournaloftheAmericanChemicalSociety " (JACS) the 49th phase 18072-18074 page, and the method that this article proposes to utilize N-heterocyclic carbine to cause the ring-opening polymerization of N-substituted glycinic acid-N-carboxylic acid prepares class polypeptide.But N-heterocyclic carbine is extremely active, and in fact responsive to empty G&W, the aerial life-span is only several seconds, and direct catalyzed ring opening polymerization needs very harsh condition, and therefore these class methods are not suitable for extensive synthesis.Subsequently, Luxenhofer etc. deliver " PolypeptoidsfromN-SubstitutedGlycineN-Carboxyanhydrides: Hydrophilic at " Macromolecules " (macromole) the 44th phase 6746-6758 page, Hydrophobic, andAmphiphilicPolymerswithPoissonDistribution " (the polypeptide from N-substituted glycinic acid-N-carboxylic acid: hydrophobic, hydrophilic, parents notion), class polypeptide is prepared in the ring-opening polymerization that this paper report utilizes benzylamine to cause N-substituted glycinic acid-N-carboxylic acid under vacuum, but high vacuum condition is not suitable for suitability for industrialized production, therefore present method have also been obtained restriction.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, provides a kind of method of simple efficient synthesis class polypeptide.The present invention utilizes the ring-opening polymerization of primary amine initiation N-substituted glycinic acid-N-carboxylic acid under without glove box strategy (nitrogen gas stream) to prepare class polypeptide.The method is simple to operate, reasonable in design, is applicable to suitability for industrialized production.
The object of the invention is to be achieved through the following technical solutions, the present invention is completed by single step reaction, namely with kiber alkyl amine or aromatic primary amine for initiator, with N-substituted glycinic acid-N-carboxylic acid for monomer, under nitrogen gas stream condition, class polypeptide is prepared in the solution ring-opening polymerization of primary amine initiation N-substituted glycinic acid-N-carboxylic acid.
Described N-substituted glycinic acid-N-carboxylic acid is N-alkyl substituted glycinic acid-N-carboxylic acid or N-aromatic base substituted glycinic acid-N-carboxylic acid.
Described N-alkyl substituted glycinic acid-N-carboxylic acid monomer is:
Described N-aromatic base substituted glycinic acid-N-carboxylic acid is:
Described monomer and the mol ratio of initiator are 1: 25 ~ 1: 300.
Described initiator primary amine is kiber alkyl amine or aromatic primary amine.
Described solution ring-opening polymerization polymer, ie in solution is tetrahydrofuran (THF), methylene dichloride, toluene, acetonitrile.
Described nitrogen gas stream condition, namely in two neck reaction flask, a neck pours nitrogen, and another eck flows out nitrogen, is the carbonic acid gas produced in reflection process, easier discharge.The flow rates of nitrogen gas stream is 100 ~ 300mL/min.
Described kiber alkyl amine is
Described aromatic primary amine is
Described solution ring-opening polymerization carries out under room temperature 20 ~ 30 DEG C of conditions, and polymerization reaction time is 4 ~ 25 hours.
Described primary amine causes the ring-opening polymerization of N-substituted glycinic acid-N-carboxylic acid, the class polypeptide of linear structure that obtained is.
Class polypeptide prepared by described synthetic method is linear α-class polypeptide.
Synthetic route of the present invention is as follows:
Beneficial effect:
Tool of the present invention has the following advantages:
(1) adopt the mode of nitrogen gas stream to be taken out of rapidly by the carbonic acid gas of the generation in reaction process, speed of reaction is improved, be beneficial to polyreaction and occur;
(2) this method polymerization produce class polypeptide molecular weight narrow distribution and molecular weight can be controlled very well;
(3) for preparation feedback biomaterial provides a kind of simple and effective approach.
Accompanying drawing explanation
Fig. 1 is synthesizer figure of the present invention
Wherein, 1 is magnetic stirring apparatus; 2 is double-neck flasks; 3 is beakers.
Fig. 2 is the hydrogen spectrum of the class polypeptide that the embodiment of the present invention 1 is synthesized.
Fig. 3 is the carbon spectrogram of the class polypeptide that the embodiment of the present invention 1 is synthesized.
Fig. 4 is the polymerization kinetics curves figure of embodiment 1.
Embodiment
The present invention's following examples illustrate, but the present invention is not limited to following embodiment, and under the scope not departing from the described aim in front and back, change is included in technical scope of the present invention.
Embodiment 1
As shown in Figure 1, under nitrogen gas stream condition, by N-methyl substituted glycine-N-carboxylic acid (0.2581g, 2.3mmol) be dissolved in 2.3mL anhydrous acetonitrile, after dissolving completely, with microsyringe, benzylamine (10uL, 0.092mmol) is joined ([monomer] in solution
0/ [initiator
0]=25).Reaction soln is room temperature reaction under nitrogen flowing.React after 4 hours, reaction solution joins in excess diethyl ether, separates out polymkeric substance, then vacuum-drying polymkeric substance.Polymer architecture passes through
1hNMR with
13cNMR identifies (see Fig. 2 and Fig. 3), and the molecular weight of polymkeric substance and dispersity are measured by GPC (gel permeation chromatograph).GPC test condition: flow velocity 1mL/min, moving phase DMF, temperature 50 C.From Fig. 4 reaction power curve, we find having under nitrogen gas stream effect, and speed of reaction significantly improves.(number-average molecular weight is 1.9kg/mol; Molecular weight distribution is 1.06; Productive rate 91.5%).
Embodiment 2
Under nitrogen gas stream condition, N-methyl substituted glycine-N-carboxylic acid (3.097g, 27.6mmol) is dissolved in 27.6mL anhydrous methylene chloride, after dissolving completely, with microsyringe, propylamine (7.5uL, 0.092mmol) is joined ([monomer] in solution
0/ [initiator
0]=300).Reaction soln is room temperature reaction under nitrogen flowing.React after 4 hours, reaction solution joins in excess diethyl ether, separates out polymkeric substance, then vacuum-drying polymkeric substance.Polymer architecture passes through
1hNMR with
13cNMR identifies, the molecular weight of polymkeric substance and dispersity are measured by GPC (gel permeation chromatograph).GPC test condition: flow velocity 1mL/min, moving phase DMF, temperature 50 C.(number-average molecular weight is 20.7kg/mol; Molecular weight distribution is 1.08; Productive rate 92.1%).
Embodiment 3
Under nitrogen gas stream condition, N-ethyl substituted glycinic acid-N-carboxylic acid (1.1860g, 9.2mmol) is dissolved in 9.2mL anhydrous acetonitrile, after dissolving completely, with microsyringe, benzylamine (10uL, 0.092mmol) is joined ([monomer] in solution
0/ [initiator
0]=100).Reaction soln is room temperature reaction under nitrogen flowing.React after 8 hours, reaction solution joins in excess diethyl ether, separates out polymkeric substance, then vacuum-drying polymkeric substance.Polymer architecture passes through
1hNMR with
13cNMR identifies, the molecular weight of polymkeric substance and dispersity are measured by GPC (gel permeation chromatograph).GPC test condition: flow velocity 1mL/min, moving phase DMF, temperature 50 C.(number-average molecular weight is 1.8kg/mol; Molecular weight distribution is 1.22; Productive rate is 86.1%).
Embodiment 4
Under nitrogen gas stream condition, N-propyl group substituted glycinic acid-N-carboxylic acid (0.6584g, 4.6mmol) is dissolved in 4.6mL anhydrous acetonitrile, after dissolving completely, with microsyringe, benzylamine (10uL, 0.092mmol) is joined ([monomer] in solution
0/ [initiator
0]=50).Reaction soln is room temperature reaction under nitrogen flowing.React after 24 hours, reaction solution joins in excess diethyl ether, separates out polymkeric substance, then vacuum-drying polymkeric substance.Polymer architecture passes through
1hNMR with
13cNMR identifies, the molecular weight of polymkeric substance and dispersity are measured by GPC (gel permeation chromatograph).GPC test condition: flow velocity 1mL/min, moving phase DMF, temperature 50 C.(number-average molecular weight is 2.7kg/mol; Molecular weight distribution is 1.18; Productive rate is 85.6%).
Embodiment 5
Under nitrogen gas stream condition, N-butyl substituted glycinic acid-N-carboxylic acid (0.3614g, 2.3mmol) is dissolved in 2.3mL anhydrous tetrahydro furan, after dissolving completely, with microsyringe, benzylamine (10uL, 0.092mmol) is joined ([monomer] in solution
0/ [initiator
0]=25).Reaction soln is room temperature reaction under nitrogen flowing.React after 24 hours, reaction solution joins in excess diethyl ether, separates out polymkeric substance, then vacuum-drying polymkeric substance.Polymer architecture passes through
1hNMR with
13cNMR identifies, the molecular weight of polymkeric substance and dispersity are measured by GPC (gel permeation chromatograph).GPC test condition: flow velocity 1mL/min, moving phase DMF, temperature 50 C.(number-average molecular weight is 2.3kg/mol; Molecular weight distribution is 1.17; Productive rate is 87.1%).
Embodiment 6
Under nitrogen gas stream condition, by N-(S) styroyl substituted glycinic acid-N-carboxylic acid (0.4720g, 2.3mmol) be dissolved in 2.3mL anhydrous acetonitrile, after dissolving completely, with microsyringe, benzylamine (10uL, 0.092mmol) is joined ([monomer] in solution
0/ [initiator
0]=25).Reaction soln is room temperature reaction under nitrogen flowing.React after 24 hours, reaction solution joins in excess diethyl ether, separates out polymkeric substance, then vacuum-drying polymkeric substance.Polymer architecture passes through
1hNMR with
13cNMR identifies, the molecular weight of polymkeric substance and dispersity are measured by GPC (gel permeation chromatograph).GPC test condition: flow velocity 1mL/min, moving phase DMF, temperature 50 C.(number-average molecular weight is 3.8kg/mol; Molecular weight distribution is 1.22; Productive rate is 86.3%).
Embodiment 7
Under nitrogen gas stream condition, by N-(R) styroyl substituted glycinic acid-N-carboxylic acid (0.4720g, 2.3mmol) be dissolved in 2.3mL dry toluene, after dissolving completely, with microsyringe, benzylamine (10uL, 0.092mmol) is joined ([monomer] in solution
0/ [initiator
0]=25).Reaction soln is room temperature reaction under nitrogen flowing.React after 24 hours, reaction solution joins in excess diethyl ether, separates out polymkeric substance, then vacuum-drying polymkeric substance.Polymer architecture passes through
1hNMR with
13cNMR identifies, the molecular weight of polymkeric substance and dispersity are measured by GPC (gel permeation chromatograph).GPC test condition: flow velocity 1mL/min, moving phase DMF, temperature 50 C.(number-average molecular weight is 3.8kg/mol; Molecular weight distribution is 1.22; Productive rate is 85.3%).
Claims (10)
1. the synthetic method of a kind polypeptide, is characterized in that, with kiber alkyl amine or aromatic primary amine for initiator, with N-substituted glycinic acid-N-carboxylic acid for monomer, and the solution ring-opening polymerization of trigger monomer under nitrogen flowing, one-step synthesis class polypeptide.
2. synthetic method according to claim 1, is characterized in that, described N-substituted glycinic acid-N-carboxylic acid is N-alkyl substituted glycinic acid-N-carboxylic acid or N-aromatic base substituted glycinic acid-N-carboxylic acid.
3. synthetic method according to claim 2, is characterized in that, described N-alkyl substituted glycinic acid-N-carboxylic acid monomer is:
4. synthetic method according to claim 2, is characterized in that, described N-aromatic base substituted glycinic acid-N-carboxylic acid is:
5. the synthetic method according to Claims 1-4 any one, is characterized in that, described monomer and the mol ratio of initiator are 1: 25 ~ 1: 300.
6. the synthetic method according to Claims 1-4 any one, is characterized in that, described nitrogen gas stream, and namely in two neck reaction flask, a neck pours nitrogen, and another neck flows out nitrogen, and the flow rates of nitrogen gas stream is 100 ~ 300mL/min.
7. the synthetic method according to Claims 1-4 any one, is characterized in that, described solution ring-opening polymerization carries out under 20 ~ 30 DEG C of conditions, and the ring-opening polymerization time is 4 ~ 25 hours.
8. the synthetic method according to Claims 1-4 any one, is characterized in that, described kiber alkyl amine is
9. the synthetic method according to Claims 1-4 any one, is characterized in that, described aromatic primary amine is
10. the synthetic method according to Claims 1-4 any one, is characterized in that, described solution is: tetrahydrofuran (THF), acetonitrile, toluene, methylene dichloride.
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| CN201510763055.2A CN105199098A (en) | 2015-11-10 | 2015-11-10 | Synthetic method of polypeptide-like compound |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107226906A (en) * | 2017-06-15 | 2017-10-03 | 南京工业大学 | Preparation method of clustered peptide block copolymer |
| US11123433B2 (en) * | 2016-06-01 | 2021-09-21 | Board Of Supervisors Of Louisiana State University | Hydrophobically modified polypeptoids and uses thereof |
| WO2022062288A1 (en) * | 2020-09-28 | 2022-03-31 | 苏州大学 | Aniline anhydride, preparation method therefor, and polyaminoacid graft chain |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102012208886A1 (en) * | 2011-05-27 | 2012-11-29 | Technische Universität Dresden | New amphiphilic copolymer comprising two keto-amine structural units excluding keto-amine diblock copolymers, useful as non-ionic soaps, emulsifiers, membrane structures, defoamers, viscosity reducers and auxiliaries for pesticides |
| CN103289078A (en) * | 2013-05-17 | 2013-09-11 | 中山大学 | Method for rapidly preparing polyamino acid and derivative thereof and application of method |
-
2015
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102012208886A1 (en) * | 2011-05-27 | 2012-11-29 | Technische Universität Dresden | New amphiphilic copolymer comprising two keto-amine structural units excluding keto-amine diblock copolymers, useful as non-ionic soaps, emulsifiers, membrane structures, defoamers, viscosity reducers and auxiliaries for pesticides |
| CN103289078A (en) * | 2013-05-17 | 2013-09-11 | 中山大学 | Method for rapidly preparing polyamino acid and derivative thereof and application of method |
Non-Patent Citations (3)
| Title |
|---|
| JIONG ZOU ET AL: "A Facile Glovebox-Free Strategy To Significantly Accelerate the Syntheses of Well-Defined Polypeptides by N-Carboxyanhydride (NCA) Ring-Opening Polymerizations", 《MACROMOLECULES》 * |
| LI GUO ET AL: "STN-1 21597_ftpSynthesis and characterization of cyclic and linear helical poly(α-peptoid)s by N -heterocyclic carbene-mediated ring-opening polymerizations of N -substituted N-carboxyanhydrides", 《BIOPOLYMERS (PEPTIDE SCIENCE)》 * |
| SAIDE CUI ET AL: "One-Pot Glovebox-Free Synthesis, Characterization, and Self-Assembly of Novel Amphiphilic Poly(Sarcosine-b-Caprolactone) Diblock Copolymers", 《MACROMOLECULAR RAPID COMMUNICATIONS》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11123433B2 (en) * | 2016-06-01 | 2021-09-21 | Board Of Supervisors Of Louisiana State University | Hydrophobically modified polypeptoids and uses thereof |
| CN107226906A (en) * | 2017-06-15 | 2017-10-03 | 南京工业大学 | Preparation method of clustered peptide block copolymer |
| WO2022062288A1 (en) * | 2020-09-28 | 2022-03-31 | 苏州大学 | Aniline anhydride, preparation method therefor, and polyaminoacid graft chain |
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Application publication date: 20151230 |