CN112522339A - Method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine with chitin - Google Patents
Method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine with chitin Download PDFInfo
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- CN112522339A CN112522339A CN202011503133.2A CN202011503133A CN112522339A CN 112522339 A CN112522339 A CN 112522339A CN 202011503133 A CN202011503133 A CN 202011503133A CN 112522339 A CN112522339 A CN 112522339A
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- chitin
- 3a5af
- nag
- chloride
- glucosamine
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- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 title claims abstract description 55
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 title claims abstract description 55
- 229950006780 n-acetylglucosamine Drugs 0.000 title claims abstract description 55
- 229920002101 Chitin Polymers 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims abstract description 24
- GPLHPEIJJXDRBA-UHFFFAOYSA-N n-(5-acetylfuran-3-yl)acetamide Chemical compound CC(=O)NC1=COC(C(C)=O)=C1 GPLHPEIJJXDRBA-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 230000000593 degrading effect Effects 0.000 title claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 65
- 102000012286 Chitinases Human genes 0.000 claims abstract description 27
- 108010022172 Chitinases Proteins 0.000 claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims abstract description 18
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000758 substrate Substances 0.000 claims abstract description 12
- 229910052751 metal Inorganic materials 0.000 claims abstract description 4
- 239000002184 metal Substances 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- 239000013078 crystal Substances 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 239000012043 crude product Substances 0.000 claims description 33
- 239000007787 solid Substances 0.000 claims description 32
- 238000001914 filtration Methods 0.000 claims description 15
- 239000006228 supernatant Substances 0.000 claims description 14
- 239000008367 deionised water Substances 0.000 claims description 13
- 229910021641 deionized water Inorganic materials 0.000 claims description 13
- 238000001035 drying Methods 0.000 claims description 13
- 238000004108 freeze drying Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
- LLSDKQJKOVVTOJ-UHFFFAOYSA-L calcium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ca+2] LLSDKQJKOVVTOJ-UHFFFAOYSA-L 0.000 claims description 7
- 229940052299 calcium chloride dihydrate Drugs 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004327 boric acid Substances 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 239000008055 phosphate buffer solution Substances 0.000 claims description 3
- 239000001103 potassium chloride Substances 0.000 claims description 3
- 235000011164 potassium chloride Nutrition 0.000 claims description 3
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 229910021380 Manganese Chloride Inorganic materials 0.000 claims description 2
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 2
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 claims description 2
- JGDITNMASUZKPW-UHFFFAOYSA-K aluminium trichloride hexahydrate Chemical compound O.O.O.O.O.O.Cl[Al](Cl)Cl JGDITNMASUZKPW-UHFFFAOYSA-K 0.000 claims description 2
- 229940009861 aluminum chloride hexahydrate Drugs 0.000 claims description 2
- 235000019270 ammonium chloride Nutrition 0.000 claims description 2
- PWHCIQQGOQTFAE-UHFFFAOYSA-L barium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ba+2] PWHCIQQGOQTFAE-UHFFFAOYSA-L 0.000 claims description 2
- GFHNAMRJFCEERV-UHFFFAOYSA-L cobalt chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Co+2] GFHNAMRJFCEERV-UHFFFAOYSA-L 0.000 claims description 2
- 229940044631 ferric chloride hexahydrate Drugs 0.000 claims description 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 claims description 2
- 239000011565 manganese chloride Substances 0.000 claims description 2
- 235000002867 manganese chloride Nutrition 0.000 claims description 2
- 229940099607 manganese chloride Drugs 0.000 claims description 2
- 229910021645 metal ion Inorganic materials 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims description 2
- 229940116357 potassium thiocyanate Drugs 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 claims description 2
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 101000895977 Amycolatopsis orientalis Exo-beta-D-glucosaminidase Proteins 0.000 claims 1
- RHPRMPZCKXOVCW-UHFFFAOYSA-J O.O.O.O.O.O.[Cl-].[Mg+2].[Ca+2].[Cl-].[Cl-].[Cl-] Chemical compound O.O.O.O.O.O.[Cl-].[Mg+2].[Ca+2].[Cl-].[Cl-].[Cl-] RHPRMPZCKXOVCW-UHFFFAOYSA-J 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 7
- 230000008901 benefit Effects 0.000 abstract description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000000178 monomer Substances 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 239000007810 chemical reaction solvent Substances 0.000 abstract 1
- 238000006210 cyclodehydration reaction Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 description 16
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 10
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 10
- 239000001110 calcium chloride Substances 0.000 description 10
- 229910001628 calcium chloride Inorganic materials 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- 239000003456 ion exchange resin Substances 0.000 description 10
- 229920003303 ion-exchange polymer Polymers 0.000 description 10
- 238000003760 magnetic stirring Methods 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 238000001291 vacuum drying Methods 0.000 description 10
- 239000008363 phosphate buffer Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002245 particle Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002608 ionic liquid Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000002028 Biomass Substances 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- -1 nitrogen-containing compound Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000238557 Decapoda Species 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 1
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 description 1
- NMTRJAKSMWDJSY-UHFFFAOYSA-N Pyrrolosine Natural products C=1OC=2C(N)=NC=NC=2C=1C1OC(CO)C(O)C1O NMTRJAKSMWDJSY-UHFFFAOYSA-N 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- XBOHKUPCELBZPH-UHFFFAOYSA-N furan-2,3-diamine Chemical compound NC=1C=COC=1N XBOHKUPCELBZPH-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 1
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/66—Nitrogen atoms
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Abstract
The invention relates to preparation of chemicals, in particular to a method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine by using chitin, which is a nitrogen-containing platform compound with high added value, can be used for various nitrogen-containing fine chemical synthesis and has great application value. The method comprises the steps of firstly degrading chitin by using chitinase to serve as a monomer N-acetyl-D-glucosamine, then using the chitin as a starting substrate, using N, N-dimethylacetamide as a reaction solvent, and carrying out cyclodehydration to form 3A5AF under the action of catalysts such as ammonium thiocyanate and structural analogues thereof and a small amount of metal salt serving as auxiliary catalysts. The method has the advantages of simple reaction steps, low catalyst cost, convenient operation, high product yield and better industrialization prospect.
Description
Technical Field
The invention belongs to the field of biomass conversion, and particularly relates to a method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine with chitin.
Background
The nitrogen-containing compound is an important chemical, has important application value in the fields of chemical industry, medicine and materials, is generally synthesized from nonrenewable fossil resources such as coal, petroleum and the like, needs an additional amino donor, and has high energy consumption, low conversion rate and poor economic benefit.
Chitin (C)8H13O5N)nThe polymer, also called chitin, formed by bonding NAG through beta-1, 4 glycosidic bonds, is widely distributed in nature, mainly exists in exoskeletons of shrimps, crabs, insects and the like, has the content second to cellulose, and is the second most renewable resource in the world. The chitin structure contains nitrogen element, and is an excellent substrate for synthesizing nitrogen-containing chemicals. Therefore, the chitin is directly converted into the nitrogen-containing compound with high added value, which not only brings great economic benefits to the modern society, but also has important significance for waste treatment and environmental protection.
3-acetamido-5-acetylfuran (3A5AF) is a nitrogen-containing platform compound with high added value, which can be obtained from chitin, and has great application prospect and research value in the field of synthesis of nitrogen-containing fine chemicals. For example, 3A5AF is an important component of several bioactive macromolecular compounds, including the anticancer agent, proximicin a, the alkaloids, hyposeragine a and B, and pyrrolosine, among others. In addition, the method can also be used for synthesizing furan diamine chemicals.
At present, the synthesis of 3A5AF by using chitin and its monomer NAG as substrates has been reported. For example, Yan et al prepared 3A5AF with chitin as the substrate in 7.5% yield. However, the yield of 3A5AF was low with chitin as substrate, a maximum of 18%. The yield can be effectively improved by taking the degradation product NAG of the chitin as a substrate. FRANICH et al reported pyrolysis of NAG at high temperature to give the nitrogen-containing compound 3A5 AF. Drover et al reported that boric acid was added at 180 deg.C[B(OH)3]In the presence of ionic liquid NAG was converted to 3A5AF in 60% yield. Omari et al 220 ℃ in B (OH)3And NaCl in the presence of conversion of NAG to 3A5AF with microwave irradiation in 58% yield. However, in the reported research, ionic liquid is mostly used as a catalyst, the price is expensive, and the production cost is high due to the substrate.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a method for preparing 3-acetamido-5-acetylfuran (3A5AF) by degrading N-acetyl-D-glucosamine (NAG) with chitin, the method utilizes a green biological enzyme method to degrade renewable biomass chitin into N-acetyl-D-glucosamine by chitinase, and further utilizes a chemical catalysis method to synthesize NAG into 3A5AF with high added value under the conditions that N, N-dimethylacetamide is used as a solvent, ammonium thiocyanate and structural analogues thereof are used as catalysts, and metal salt is added as a cocatalyst.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
a method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine with chitin comprises the following steps:
step 1, adding chitinase, phosphate buffer solution and metal ions into chitin, carrying out enzymolysis for 24-120 h at the temperature of 30-50 ℃ and the pH value of 6-8, separating supernatant after the enzymolysis is finished, and then carrying out adsorption, vacuum concentration and freeze drying on the supernatant to obtain NAG crystals;
and 2, adding 5mL of solvent into NAG, a catalyst and a metal salt cocatalyst into a pressure-resistant tube for dissolving, heating for reacting for 5-240 min, filtering, taking filtrate, adding water with the same volume into the filtrate for mixing, extracting with ethyl acetate for three times, combining extract liquor after extracting for three times, concentrating under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol for redissolving, dropwise adding into precooled deionized water for crystallization, filtering and drying to obtain a transparent needle-shaped 3A5AF crystal with the purity higher than 99.5%.
The improvement is that the chitinase is one or a mixture of two of chitinase endoenzyme, chitinase exoenzyme or N-acetamidohexosidase.
The improvement is that the dosage of the chitin is 0.025g-1g, the dosage of the NAG is 0.025g-1g, the mass of the catalyst is 0.1-5 times of that of the NAG substrate, and the mass of the cocatalyst is 0.1-5 times of that of the NAG substrate.
The improvement is that the catalyst is one or the mixture of any two of ammonium thiocyanate, thiourea, potassium thiocyanate, thiobenzamide, thioacetamide or thiosemicarbazide.
The improvement is that the solvent in the step 2 is one or a mixture of any two of N-methylpyrrolidone, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide and ethanol, and the dosage of the solvent is 1-100 mL.
The improvement is that the cocatalyst is one or the mixture of any two of boric acid, sodium chloride, potassium chloride, lithium chloride, ammonium chloride, zinc chloride, aluminum chloride hexahydrate, cobalt chloride hexahydrate, magnesium chloride hexahydrate, calcium chloride dihydrate, barium chloride dihydrate, ferric chloride hexahydrate, manganese chloride, hydrogen chloride and 1-butyl-3-methylimidazolium chloride salt.
As a modification, the reaction temperature in step 2 is 120-200 ℃.
Has the advantages that:
compared with the prior art, the method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine by using chitin utilizes the renewable biomass resource chitin monomer NAG as a raw material to prepare 3A5AF, thereby widening the research on effective utilization of biomass; the cheap and easily obtained ammonium thiocyanate is used as the catalyst, so that the production cost of 3A5AF is greatly reduced, and the industrial production of 3A5AF is facilitated.
Drawings
FIG. 1 shows the results of liquid phase detection of 3A5 AF;
FIG. 2 is a liquid phase detection result of NAG after 45min reaction under a catalyst.
Detailed Description
The following examples are provided to aid in a further understanding of the invention.
Example 1
Converting chitin with chitinase in 200mL reaction system (chitin powder 40 g/L, chitinase 1.3U/mL, N-acetylhexosaminidase 1.35U/mL, CaCl2 15 mM, phosphate buffer solution with pH 8), reacting at 37 ℃ and 200rpm for 36 h under stirring, separating supernatant after the reaction is finished, adsorbing by ion exchange resin, concentrating in vacuum, and freeze-drying to obtain NAG crystal.
Then 100mg NAG and 50mg ammonium thiocyanate (catalyst) are put into a 50mL pressure resistant tube, 5mL N, N-dimethylacetamide (solvent) is added, and the mixture is heated and stirred for 45min at 180 ℃ in a magnetic stirring heater under the pressure condition. After the reaction is finished and cooled to room temperature, adding pure water with the same volume as the reaction product, dissolving the mixture in water, extracting the mixture for multiple times by using ethyl acetate, concentrating the mixture under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol to redissolve the solid crude product, dropwise adding the solid crude product into precooled deionized water to crystallize, filtering and drying the crystals to obtain the high-purity (99.5%) transparent needle-shaped 3A5AF crystal. The liquid phase found that the concentration of 3A5AF in the reaction mixture was 4.43g/L and the molar conversion was 29.31%.
Example 2
Converting chitin with chitinase, wherein the reaction system (chitin powder particle 40 g/L, chitinase 1.3U/mL, N-acetylhexosaminidase 1.35U/mL, CaCl2 15 mM, pH 8 phosphate buffer) at 37 ℃ under 200rpm for 36 h, separating the supernatant after the reaction is finished, adsorbing by ion exchange resin, concentrating in vacuum, and freeze-drying to obtain NAG crystal.
Then 100mg NAG and 50mg ammonium thiocyanate are put into a 50mL pressure resistant tube, 5mL dimethyl sulfoxide (solvent) is added, and the mixture is heated and stirred for 45min at 180 ℃ in a magnetic stirring heater under the condition of pressurization. After the reaction is finished and cooled to room temperature, adding pure water with the same volume as the reaction product, dissolving the mixture in water, extracting the mixture for multiple times by using ethyl acetate, concentrating the mixture under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol to redissolve the solid crude product, dropwise adding the solid crude product into precooled deionized water to crystallize, filtering and drying the crystals to obtain the high-purity (99.5%) transparent needle-shaped 3A5AF crystal. The liquid phase measurement shows that the concentration of 3A5AF in the reaction solution is 0.15g/L, and the molar conversion rate is 0.99%.
Example 3
Converting chitin with chitinase, wherein the reaction system (chitin powder particle 40 g/L, chitinase 1.3U/mL, N-acetylhexosaminidase 1.35U/mL, CaCl2 15 mM, pH 8 phosphate buffer) at 37 ℃ under 200rpm for 36 h, separating the supernatant after the reaction is finished, adsorbing by ion exchange resin, concentrating in vacuum, and freeze-drying to obtain NAG crystal.
Then 100mg NAG and 50mg ammonium thiocyanate are put into a 50mL pressure resistant tube, 5mL N-methyl pyrrolidone (solvent) is added, and the mixture is heated and stirred for 45min at 180 ℃ in a magnetic stirring heater under the pressure condition. After the reaction is finished and cooled to room temperature, adding pure water with the same volume as the reaction product, dissolving the mixture in water, extracting the mixture for multiple times by using ethyl acetate, concentrating the mixture under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol to redissolve the solid crude product, dropwise adding the solid crude product into precooled deionized water to crystallize, filtering and drying the crystals to obtain the high-purity (99.5%) transparent needle-shaped 3A5AF crystal. The liquid phase measurement shows that the concentration of 3A5AF in the reaction solution is 1.00g/L, and the molar conversion rate is 6.60%.
Example 4
Converting chitin with chitinase, wherein the reaction system (chitin powder particle 40 g/L, chitinase 1.3U/mL, N-acetylhexosaminidase 1.35U/mL, CaCl2 15 mM, pH 8 phosphate buffer) at 37 ℃ under 200rpm for 36 h, separating the supernatant after the reaction is finished, adsorbing by ion exchange resin, concentrating in vacuum, and freeze-drying to obtain NAG crystal.
Then 100mg NAG, 50mg ammonium thiocyanate and 0.0132g sodium chloride are taken, 5mL of N, N-dimethylacetamide is added into a 50mL pressure resistant tube, and the mixture is heated and stirred for 45min at 180 ℃ in a magnetic stirring heater under the pressure condition. After the reaction is finished and cooled to room temperature, adding pure water with the same volume as the reaction product, dissolving the mixture in water, extracting the mixture for multiple times by using ethyl acetate, concentrating the mixture under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol to redissolve the solid crude product, dropwise adding the solid crude product into precooled deionized water to crystallize, filtering and drying the crystals to obtain the high-purity (99.5%) transparent needle-shaped 3A5AF crystal. The liquid phase measurement shows that the concentration of 3A5AF in the reaction solution is 5.66g/L, and the molar conversion rate is 37.43%.
Example 5
Converting chitin with chitinase, wherein the reaction system (chitin powder particle 40 g/L, chitinase 1.3U/mL, N-acetylhexosaminidase 1.35U/mL, CaCl2 15 mM, pH 8 phosphate buffer) at 37 ℃ under 200rpm for 36 h, separating the supernatant after the reaction is finished, adsorbing by ion exchange resin, concentrating in vacuum, and freeze-drying to obtain NAG crystal.
Then 100mg NAG, 50mg ammonium thiocyanate and 0.067g calcium chloride dihydrate are taken, 5mL of N, N-dimethylacetamide is added into a 50mL pressure resistant tube, and the mixture is heated and stirred for 45min at 180 ℃ in a magnetic stirring heater under the pressure condition. After the reaction is finished and cooled to room temperature, adding pure water with the same volume as the reaction product, dissolving the mixture in water, extracting the mixture for multiple times by using ethyl acetate, concentrating the mixture under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol to redissolve the solid crude product, dropwise adding the solid crude product into precooled deionized water to crystallize, filtering and drying the crystals to obtain the high-purity (99.5%) transparent needle-shaped 3A5AF crystal. The liquid phase showed that the 3A5AF concentration in the reaction mixture was 6.53g/L, the molar conversion was 43.24%.
Example 6
Converting chitin with chitinase, wherein the reaction system (chitin powder particle 40 g/L, chitinase 1.3U/mL, N-acetylhexosaminidase 1.35U/mL, CaCl2 15 mM, pH 8 phosphate buffer) at 37 ℃ under 200rpm for 36 h, separating the supernatant after the reaction is finished, adsorbing by ion exchange resin, concentrating in vacuum, and freeze-drying to obtain NAG crystal.
Then 100mg NAG, 50mg ammonium thiocyanate and 0.034 potassium chloride are taken, 5mL of N, N-dimethylacetamide is added into a 50mL pressure resistant tube, and the mixture is heated and stirred for 45min at 180 ℃ in a magnetic stirring heater under the pressure condition. After the reaction is finished and cooled to room temperature, adding pure water with the same volume as the reaction product, dissolving the mixture in water, extracting the mixture for multiple times by using ethyl acetate, concentrating the mixture under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol to redissolve the solid crude product, dropwise adding the solid crude product into precooled deionized water to crystallize, filtering and drying the crystals to obtain the high-purity (99.5%) transparent needle-shaped 3A5AF crystal. The liquid phase measurement shows that the concentration of 3A5AF in the reaction solution is 5.38g/L, and the molar conversion rate is 35.58%.
Example 7
Using chitinaseConverting chitin, wherein the reaction system (chitin powder 40 g/L, chitinase 1.3U/mL, N-acetylhexosaminidase 1.35U/mL, CaCl2 15 mM, pH 8 phosphate buffer) at 37 ℃ under 200rpm for 36 h, separating the supernatant after the reaction is finished, adsorbing by ion exchange resin, concentrating in vacuum, and freeze-drying to obtain NAG crystal.
Then 100mg NAG, 50mg ammonium thiocyanate and 0.067g calcium chloride dihydrate are taken, 5mL of N, N-dimethylacetamide is added into a 50mL pressure resistant tube, and the mixture is heated and stirred for 5min at 180 ℃ in a magnetic stirring heater under the pressure condition. After the reaction is finished and cooled to room temperature, adding pure water with the same volume as the reaction product, dissolving the mixture in water, extracting the mixture for multiple times by using ethyl acetate, concentrating the mixture under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol to redissolve the solid crude product, dropwise adding the solid crude product into precooled deionized water to crystallize, filtering and drying the crystals to obtain the high-purity (99.5%) transparent needle-shaped 3A5AF crystal. The liquid phase found that the concentration of 3A5AF in the reaction mixture was 7.28g/L and the molar conversion was 48.14%.
Example 8
Converting chitin with chitinase, wherein the reaction system (chitin powder particle 40 g/L, chitinase 1.3U/mL, N-acetylhexosaminidase 1.35U/mL, CaCl2 15 mM, pH 8 phosphate buffer) at 37 ℃ under 200rpm for 36 h, separating the supernatant after the reaction is finished, adsorbing by ion exchange resin, concentrating in vacuum, and freeze-drying to obtain NAG crystal.
Then 100mg NAG, 50mg ammonium thiocyanate and 0.067g calcium chloride dihydrate are taken, 5mL of N, N-dimethylacetamide is added into a 50mL pressure resistant tube, and the mixture is heated and stirred for 30min at 180 ℃ in a magnetic stirring heater under the pressure condition. After the reaction is finished and cooled to room temperature, adding pure water with the same volume as the reaction product, dissolving the mixture in water, extracting the mixture for multiple times by using ethyl acetate, concentrating the mixture under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol to redissolve the solid crude product, dropwise adding the solid crude product into precooled deionized water to crystallize, filtering and drying the crystals to obtain the high-purity (99.5%) transparent needle-shaped 3A5AF crystal. The liquid phase measurement shows that the concentration of 3A5AF in the reaction solution is 7.45g/L, and the molar conversion rate is 49.30%.
Example 9
Converting chitin with chitinase, wherein the reactantThe system (chitin powder particle 40 g/L, chitin incision enzyme 1.3U/mL, N-acetaminohexosidase 1.35U/mL, CaCl2 15 mM, pH 8 phosphate buffer) at 37 ℃ under 200rpm for 36 h, separating the supernatant after the reaction is finished, adsorbing by ion exchange resin, concentrating in vacuum, and freeze-drying to obtain NAG crystal.
Then 100mg NAG, 50mg ammonium thiocyanate and 0.067g calcium chloride dihydrate are taken, 5mL of N, N-dimethylacetamide is added into a 50mL pressure resistant tube, and the mixture is heated and stirred for 120min at 180 ℃ in a magnetic stirring heater under the pressure condition. After the reaction is finished and cooled to room temperature, adding pure water with the same volume as the reaction product, dissolving the mixture in water, extracting the mixture for multiple times by using ethyl acetate, concentrating the mixture under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol to redissolve the solid crude product, dropwise adding the solid crude product into precooled deionized water to crystallize, filtering and drying the crystals to obtain the high-purity (99.5%) transparent needle-shaped 3A5AF crystal. The liquid phase found that the concentration of 3A5AF in the reaction mixture was 6.76g/L and the molar conversion was 44.71%.
Example 10
Converting chitin with chitinase, wherein the reaction system (chitin powder particle 40 g/L, chitinase 1.3U/mL, N-acetylhexosaminidase 1.35U/mL, CaCl2 15 mM, pH 8 phosphate buffer) at 37 ℃ under 200rpm for 36 h, separating the supernatant after the reaction is finished, adsorbing by ion exchange resin, concentrating in vacuum, and freeze-drying to obtain NAG crystal.
Then 150mg NAG, 50mg ammonium thiocyanate and 0.075g calcium chloride dihydrate are added into a 50mL pressure resistant tube with 10mL N, N-dimethylacetamide, and heated and stirred in a magnetic stirring heater at 180 ℃ for 25min under the pressure condition. After the reaction is finished and cooled to room temperature, adding pure water with the same volume as the reaction product, dissolving the mixture in water, extracting the mixture for multiple times by using ethyl acetate, concentrating the mixture under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol to redissolve the solid crude product, dropwise adding the solid crude product into precooled deionized water to crystallize, filtering and drying the crystals to obtain the high-purity (99.5%) transparent needle-shaped 3A5AF crystal. The liquid phase found that the concentration of 3A5AF in the reaction mixture was 8.56g/L and the molar conversion was 56.66%.
Example 11
The same procedure as in example 1 was repeated except that the NAG reaction temperature was changed to 160 ℃, and the 3A5AF concentration in the reaction mixture was 1.20g/L and the molar conversion was 7.92% as measured in the liquid phase.
Example 12
In the same manner as in example 1 except that the NAG reaction temperature was changed to 170 ℃, the concentration of 3A5AF in the reaction solution was 3.12g/L and the molar conversion was 20.67% as measured in the liquid phase.
Example 13
In the same manner as in example 1 except that the NAG reaction temperature was changed to 190 ℃, the concentration of 3A5AF in the reaction solution was 4.20g/L and the molar conversion was 27.81% as measured in the liquid phase.
Example 14
The same as in example 1 except that the NAG reaction catalyst was changed to thiourea, the concentration of 3A5AF in the reaction solution was 4.18g/L and the molar conversion was 27.69%, as measured in the liquid phase.
Comparative example 1
In patent CN111072602A, amino acid ionic liquid is used as a catalyst to catalyze N-acetylglucosamine to be 3-acetamido-5-acetylfuran, which has the advantages that the catalyst raw material is cheap and easy to obtain, the highest conversion rate can reach 52.61%, but the reaction temperature reaches 200 ℃, and only a 3A5AF crude product is finally obtained. The method adopts ammonium thiocyanate as a catalyst, the optimal yield can reach 56.66% at 180 ℃, the cost of the catalyst ammonium thiocyanate is lower than that of amino acid ionic liquid, the process of preparing the ionic liquid is avoided, and the reaction process is simplified. Meanwhile, the patent provides a crystallization method for obtaining high-purity 3A5AF crystal, which is beneficial to obtaining high-purity 3A5AF product.
The invention directly starts from chitin, firstly, the chitin is degraded into NAG by a green biological enzyme method, and on the basis, low-price ammonium thiocyanate and structural analogues thereof are used as catalysts, so that the chitin can be finally efficiently converted into a platform chemical 3A5AF for chemical production.
The above-mentioned embodiments, objects, technical solutions and advantages of the present invention are further described in detail, it should be understood that the above-mentioned embodiments are only illustrative of the present invention and are not intended to limit the present invention, and any modifications, equivalents, improvements and the like made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (7)
1. A method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine with chitin is characterized by comprising the following steps:
step 1, adding chitinase, phosphate buffer solution and metal ions into chitin, carrying out enzymolysis for 24-120 h at the temperature of 30-50 ℃ and the pH value of 6-8, separating supernatant after the enzymolysis is finished, and then carrying out adsorption, vacuum concentration and freeze drying on the supernatant to obtain NAG crystals;
and 2, adding a solvent to dissolve NAG, a catalyst and a metal salt cocatalyst into a pressure-resistant tube, reacting at a set temperature, filtering after the reaction is finished, taking a filtrate, adding water with the same volume into the filtrate for mixing, extracting with ethyl acetate for three times, combining extract liquor after extracting for three times, concentrating under reduced pressure to obtain a solid crude product containing 3A5AF, adding 1mL of methanol for redissolving, dropwise adding into precooled deionized water for crystallization, filtering and drying to obtain a transparent needle-shaped 3A5AF crystal with the purity higher than 99.5%, adding 1mL of methanol for redissolving, dropwise adding into precooled deionized water for crystallization, and filtering and drying to obtain a transparent needle-shaped 3A5AF crystal with the purity higher than 99.5%.
2. The method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine with chitin according to claim 1, wherein the chitinase is one or two of endo-chitinase, exo-chitinase and N-acetylhexosaminidase.
3. The method of claim 1, wherein the chitin is used in an amount of 0.025g to 1g, the NAG is used in an amount of 0.025g to 1g, the catalyst is used in an amount of 0.1 to 5 times the molar mass of the NAG substrate, and the promoter is used in an amount of 0.1 to 5 times the molar mass of the NAG substrate.
4. The method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine with chitin according to claim 1, wherein the catalyst is one or a mixture of any two of ammonium thiocyanate, thiourea, potassium thiocyanate, thiobenzamide, thioacetamide or thiosemicarbazide, and the molar mass of the catalyst is 0.1-5 times that of NAG substrate.
5. The method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine with chitin according to claim 1, wherein the solvent in step 2 is one or a mixture of any two of N-methylpyrrolidone, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide and ethanol, and the amount of the solvent is 1-100 mL.
6. The method for preparing 3-acetamido-5-acetylfuran by degrading N-acetyl-D-glucosamine with chitin according to claim 1, wherein the promoter is one or a mixture of any two of boric acid, sodium chloride, potassium chloride, lithium chloride, ammonium chloride, zinc chloride, aluminum chloride hexahydrate, cobalt chloride hexahydrate, magnesium calcium chloride hexahydrate, calcium chloride dihydrate, barium chloride dihydrate, ferric chloride hexahydrate, manganese chloride, hydrogen chloride, and 1-butyl-3-methylimidazolium chloride.
7. The method of claim 1, wherein the reaction temperature in step 2 is 120 ℃ to 200 ℃.
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