CN106008615B - 甲壳素制备n-乙酰-d-氨基葡萄糖的方法 - Google Patents
甲壳素制备n-乙酰-d-氨基葡萄糖的方法 Download PDFInfo
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- CN106008615B CN106008615B CN201610384090.8A CN201610384090A CN106008615B CN 106008615 B CN106008615 B CN 106008615B CN 201610384090 A CN201610384090 A CN 201610384090A CN 106008615 B CN106008615 B CN 106008615B
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- Prior art keywords
- acetylamino
- deoxy
- glucose
- chitin
- prepares
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- 238000000034 method Methods 0.000 title claims abstract description 31
- 229920002101 Chitin Polymers 0.000 title claims abstract description 23
- 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 description 46
- 230000015556 catabolic process Effects 0.000 claims abstract description 16
- 238000006731 degradation reaction Methods 0.000 claims abstract description 16
- -1 acetyl D Glucosamines Chemical class 0.000 claims abstract description 14
- 239000011973 solid acid Substances 0.000 claims abstract description 12
- 238000002425 crystallisation Methods 0.000 claims abstract description 11
- 230000008025 crystallization Effects 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 20
- 239000012452 mother liquor Substances 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 14
- 235000019441 ethanol Nutrition 0.000 claims description 10
- 230000008014 freezing Effects 0.000 claims description 9
- 238000007710 freezing Methods 0.000 claims description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- 229910016287 MxOy Inorganic materials 0.000 claims description 8
- 239000003930 superacid Substances 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 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 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000003729 cation exchange resin Substances 0.000 claims description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 230000000593 degrading effect Effects 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 238000003682 fluorination reaction Methods 0.000 claims description 5
- 239000012982 microporous membrane Substances 0.000 claims description 5
- IVLXQGJVBGMLRR-UHFFFAOYSA-N 2-aminoacetic acid;hydron;chloride Chemical group Cl.NCC(O)=O IVLXQGJVBGMLRR-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 4
- 229960002449 glycine Drugs 0.000 claims description 4
- 229960001269 glycine hydrochloride Drugs 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 4
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical group FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 claims description 3
- XPFAJCSMHOQBQB-UHFFFAOYSA-N 2-aminoacetic acid;nitric acid Chemical compound O[N+]([O-])=O.NCC(O)=O XPFAJCSMHOQBQB-UHFFFAOYSA-N 0.000 claims description 3
- 239000002608 ionic liquid Substances 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
- IRSVMGYCAXSOCN-UHFFFAOYSA-N 1-butyl-3-methyl-1,2-dihydroimidazol-1-ium;methyl sulfate Chemical class COS([O-])(=O)=O.CCCC[NH+]1CN(C)C=C1 IRSVMGYCAXSOCN-UHFFFAOYSA-N 0.000 claims description 2
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical class [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 claims description 2
- AMFMJCAPWCXUEI-UHFFFAOYSA-M 1-ethylpyridin-1-ium;chloride Chemical class [Cl-].CC[N+]1=CC=CC=C1 AMFMJCAPWCXUEI-UHFFFAOYSA-M 0.000 claims description 2
- ZDNHSKGWMYYCJO-UHFFFAOYSA-N 2-aminoacetic acid 2-chloroacetic acid Chemical compound ClCC(=O)O.NCC(=O)O ZDNHSKGWMYYCJO-UHFFFAOYSA-N 0.000 claims description 2
- RMGUNXLDOFELHW-UHFFFAOYSA-N 2-aminoacetic acid;oxalic acid Chemical compound NCC(O)=O.OC(=O)C(O)=O RMGUNXLDOFELHW-UHFFFAOYSA-N 0.000 claims description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 2
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 claims description 2
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 claims description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 229960005337 lysine hydrochloride Drugs 0.000 claims description 2
- 229940049920 malate Drugs 0.000 claims description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- PLDDOISOJJCEMH-UHFFFAOYSA-N neodymium oxide Inorganic materials [O-2].[O-2].[O-2].[Nd+3].[Nd+3] PLDDOISOJJCEMH-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- DFEYYRMXOJXZRJ-UHFFFAOYSA-N sevoflurane Chemical compound FCOC(C(F)(F)F)C(F)(F)F DFEYYRMXOJXZRJ-UHFFFAOYSA-N 0.000 claims description 2
- 229960002078 sevoflurane Drugs 0.000 claims description 2
- 229950004288 tosilate Drugs 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims 1
- KIIQXOQPQGKMHD-UHFFFAOYSA-N CCNN1C=CN(C)C1.O Chemical class CCNN1C=CN(C)C1.O KIIQXOQPQGKMHD-UHFFFAOYSA-N 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical class CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 10
- 238000002360 preparation method Methods 0.000 abstract description 8
- 230000008901 benefit Effects 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000001914 filtration Methods 0.000 abstract 2
- 238000004140 cleaning Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000219094 Vitaceae Species 0.000 description 3
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 3
- 229960002442 glucosamine Drugs 0.000 description 3
- 235000021021 grapes Nutrition 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 150000002337 glycosamines Chemical class 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- OSNIIMCBVLBNGS-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-(dimethylamino)propan-1-one Chemical compound CN(C)C(C)C(=O)C1=CC=C2OCOC2=C1 OSNIIMCBVLBNGS-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-RTRLPJTCSA-N N-acetyl-D-glucosamine Chemical class CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-RTRLPJTCSA-N 0.000 description 1
- DCQRUCPVQGIYRQ-UHFFFAOYSA-N N-ethyl-3-methyl-2H-imidazol-1-amine Chemical class CN1CN(C=C1)NCC DCQRUCPVQGIYRQ-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000002772 monosaccharides Chemical group 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000021309 simple sugar Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Description
Claims (8)
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CN201610384090.8A CN106008615B (zh) | 2016-06-01 | 2016-06-01 | 甲壳素制备n-乙酰-d-氨基葡萄糖的方法 |
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CN201610384090.8A CN106008615B (zh) | 2016-06-01 | 2016-06-01 | 甲壳素制备n-乙酰-d-氨基葡萄糖的方法 |
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CN106008615A CN106008615A (zh) | 2016-10-12 |
CN106008615B true CN106008615B (zh) | 2018-07-13 |
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CN201610384090.8A Active CN106008615B (zh) | 2016-06-01 | 2016-06-01 | 甲壳素制备n-乙酰-d-氨基葡萄糖的方法 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111303220A (zh) * | 2020-03-27 | 2020-06-19 | 安徽银创生物科技股份有限公司 | D-氨基葡萄糖硫酸盐的制备方法 |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106946954A (zh) * | 2017-03-29 | 2017-07-14 | 江苏澳新生物工程有限公司 | 一种n‑乙酰‑d‑氨基葡萄糖的制备方法 |
CN110241157A (zh) * | 2019-07-05 | 2019-09-17 | 南京工业大学 | 一种六氟异丙醇预处理辅助酶法降解几丁质生产n-乙酰氨基葡萄糖的方法 |
CN110590869A (zh) * | 2019-10-09 | 2019-12-20 | 山东润德生物科技有限公司 | 一种n-乙酰氨基葡萄糖的制备方法 |
CN110590870B (zh) * | 2019-10-09 | 2020-09-01 | 山东润德生物科技有限公司 | 一种高纯度n-乙酰氨基葡萄糖的制备方法 |
CN110669082B (zh) * | 2019-10-23 | 2020-11-03 | 山东润德生物科技有限公司 | 一种n-乙酰-d-氨基葡萄糖的提纯分离方法 |
CN110684059B (zh) * | 2019-10-23 | 2020-08-28 | 山东润德生物科技有限公司 | 一种d-氨基葡萄糖硫酸盐的制备方法 |
CN110734465B (zh) * | 2019-11-08 | 2021-05-28 | 山东润德生物科技有限公司 | 一种氨基葡萄糖硫酸钾盐的制备方法 |
CN110713501B (zh) * | 2019-11-08 | 2021-04-06 | 山东润德生物科技有限公司 | 一种氨基葡萄糖硫酸钙盐的制备方法 |
CN110680906B (zh) * | 2019-11-12 | 2020-10-09 | 山东润德生物科技有限公司 | 一种氨糖骨胶肽钙颗粒剂 |
CN110818751B (zh) * | 2019-12-02 | 2020-11-10 | 山东润德生物科技有限公司 | 一种硫酸氨基葡萄糖氯化钠复盐的制备方法 |
CN110776538B (zh) * | 2019-12-02 | 2021-02-12 | 山东润德生物科技有限公司 | 一种低钾或低钠硫酸氨基葡萄糖的制备方法 |
CN111004295A (zh) * | 2019-12-09 | 2020-04-14 | 山东润德生物科技有限公司 | 一种高效合成n-乙酰氨基葡萄糖的制备方法 |
CN111647027B (zh) | 2020-06-11 | 2021-04-30 | 江苏海飞生物科技有限公司 | N-乙酰氨基葡萄糖的分离和纯化方法 |
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CN1847255A (zh) * | 2006-05-17 | 2006-10-18 | 扬州日兴生物化工制品有限公司 | N-乙酰d-氨基葡萄糖的生产方法 |
JP2009167140A (ja) * | 2008-01-18 | 2009-07-30 | Koyo Chemical Kk | N−アセチルグルコサミンの製造方法、並びにその用途 |
JP2009191001A (ja) * | 2008-02-14 | 2009-08-27 | Nankai Kagaku Kogyo Kk | 天然型n−アセチルグルコサミンの製造方法 |
CN101735288A (zh) * | 2010-01-18 | 2010-06-16 | 华东师范大学 | 一种固体酸催化糖类全乙酰化方法 |
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2016
- 2016-06-01 CN CN201610384090.8A patent/CN106008615B/zh active Active
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CN1847255A (zh) * | 2006-05-17 | 2006-10-18 | 扬州日兴生物化工制品有限公司 | N-乙酰d-氨基葡萄糖的生产方法 |
JP2009167140A (ja) * | 2008-01-18 | 2009-07-30 | Koyo Chemical Kk | N−アセチルグルコサミンの製造方法、並びにその用途 |
JP2009191001A (ja) * | 2008-02-14 | 2009-08-27 | Nankai Kagaku Kogyo Kk | 天然型n−アセチルグルコサミンの製造方法 |
CN101735288A (zh) * | 2010-01-18 | 2010-06-16 | 华东师范大学 | 一种固体酸催化糖类全乙酰化方法 |
Non-Patent Citations (1)
Title |
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N-乙酞氨基葡萄搪及D-氨基葡萄糖盐酸盐研究进展.;李辉等,;《黑龙江医药》;20071231;第20卷(第2期);第118-120页. * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111303220A (zh) * | 2020-03-27 | 2020-06-19 | 安徽银创生物科技股份有限公司 | D-氨基葡萄糖硫酸盐的制备方法 |
CN111303220B (zh) * | 2020-03-27 | 2022-03-11 | 安徽银创生物科技股份有限公司 | D-氨基葡萄糖硫酸盐的制备方法 |
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