CN111154736A - 用于制备奥利司他中间体的方法 - Google Patents
用于制备奥利司他中间体的方法 Download PDFInfo
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- CN111154736A CN111154736A CN202010015510.1A CN202010015510A CN111154736A CN 111154736 A CN111154736 A CN 111154736A CN 202010015510 A CN202010015510 A CN 202010015510A CN 111154736 A CN111154736 A CN 111154736A
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- Prior art keywords
- reaction system
- ala
- biological enzyme
- gly
- reaction
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- 238000000034 method Methods 0.000 title claims abstract description 30
- LRXRIVSWHMVULO-HKBOAZHASA-N (3s,4s,6r)-3-hexyl-4-hydroxy-6-undecyloxan-2-one Chemical class CCCCCCCCCCC[C@@H]1C[C@H](O)[C@H](CCCCCC)C(=O)O1 LRXRIVSWHMVULO-HKBOAZHASA-N 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title description 4
- 102000004190 Enzymes Human genes 0.000 claims abstract description 49
- 108090000790 Enzymes Proteins 0.000 claims abstract description 49
- XJLXINKUBYWONI-NNYOXOHSSA-O NADP(+) Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-NNYOXOHSSA-O 0.000 claims abstract description 15
- 108010050375 Glucose 1-Dehydrogenase Proteins 0.000 claims abstract description 14
- ATRNZOYKSNPPBF-CYBMUJFWSA-N (R)-3-hydroxytetradecanoic acid Chemical class CCCCCCCCCCC[C@@H](O)CC(O)=O ATRNZOYKSNPPBF-CYBMUJFWSA-N 0.000 claims abstract description 10
- BZLXCCSPPYVWKU-UHFFFAOYSA-N CCCCCCCCCCCC(=C=O)CC(=O)O Chemical compound CCCCCCCCCCCC(=C=O)CC(=O)O BZLXCCSPPYVWKU-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 239000000758 substrate Substances 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 16
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- 101001110310 Lentilactobacillus kefiri NADP-dependent (R)-specific alcohol dehydrogenase Proteins 0.000 claims description 12
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims description 10
- 229960001243 orlistat Drugs 0.000 claims description 10
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 8
- 239000000872 buffer Substances 0.000 claims description 8
- 239000008103 glucose Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 4
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 claims description 4
- 108010093096 Immobilized Enzymes Proteins 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003275 alpha amino acid group Chemical group 0.000 claims 6
- 239000003002 pH adjusting agent Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 238000006555 catalytic reaction Methods 0.000 abstract description 3
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- 108010031132 Alcohol Oxidoreductases Proteins 0.000 abstract 1
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- 239000000047 product Substances 0.000 description 23
- 150000001413 amino acids Chemical group 0.000 description 17
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- 238000004128 high performance liquid chromatography Methods 0.000 description 12
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- 238000000605 extraction Methods 0.000 description 10
- 239000003814 drug Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
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- 239000008346 aqueous phase Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 108010029645 galactitol 2-dehydrogenase Proteins 0.000 description 5
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- 230000003287 optical effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 4
- ZAZKJZBWRNNLDS-UHFFFAOYSA-N n-tetradecanoic acid methyl ester Natural products CCCCCCCCCCCCCC(=O)OC ZAZKJZBWRNNLDS-UHFFFAOYSA-N 0.000 description 4
- 108010061238 threonyl-glycine Proteins 0.000 description 4
- YYSWCHMLFJLLBJ-ZLUOBGJFSA-N Ala-Ala-Ser Chemical compound C[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(O)=O YYSWCHMLFJLLBJ-ZLUOBGJFSA-N 0.000 description 3
- 241000611852 Sphingomonas echinoides Species 0.000 description 3
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- 238000001514 detection method Methods 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- BUANFPRKJKJSRR-ACZMJKKPSA-N Ala-Ala-Gln Chemical compound C[C@H]([NH3+])C(=O)N[C@@H](C)C(=O)N[C@H](C([O-])=O)CCC(N)=O BUANFPRKJKJSRR-ACZMJKKPSA-N 0.000 description 2
- RZZMZYZXNJRPOJ-BJDJZHNGSA-N Ala-Ile-Lys Chemical compound CC[C@H](C)[C@@H](C(=O)N[C@@H](CCCCN)C(=O)O)NC(=O)[C@H](C)N RZZMZYZXNJRPOJ-BJDJZHNGSA-N 0.000 description 2
- OMMIEVATLAGRCK-BYPYZUCNSA-N Asp-Gly-Gly Chemical compound OC(=O)C[C@H](N)C(=O)NCC(=O)NCC(O)=O OMMIEVATLAGRCK-BYPYZUCNSA-N 0.000 description 2
- NSNUZSPSADIMJQ-WDSKDSINSA-N Gln-Gly-Asp Chemical compound NC(=O)CC[C@H](N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(O)=O NSNUZSPSADIMJQ-WDSKDSINSA-N 0.000 description 2
- BEQGFMIBZFNROK-JGVFFNPUSA-N Gly-Glu-Pro Chemical compound C1C[C@@H](N(C1)C(=O)[C@H](CCC(=O)O)NC(=O)CN)C(=O)O BEQGFMIBZFNROK-JGVFFNPUSA-N 0.000 description 2
- YWAQATDNEKZFFK-BYPYZUCNSA-N Gly-Gly-Ser Chemical compound NCC(=O)NCC(=O)N[C@@H](CO)C(O)=O YWAQATDNEKZFFK-BYPYZUCNSA-N 0.000 description 2
- PARSHQDZROHERM-NHCYSSNCSA-N Ile-Lys-Gly Chemical compound CC[C@H](C)[C@@H](C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)O)N PARSHQDZROHERM-NHCYSSNCSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000880493 Leptailurus serval Species 0.000 description 2
- QJXHMYMRGDOHRU-NHCYSSNCSA-N Leu-Ile-Gly Chemical compound [H]N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(O)=O QJXHMYMRGDOHRU-NHCYSSNCSA-N 0.000 description 2
- ISHNZELVUVPCHY-ZETCQYMHSA-N Lys-Gly-Gly Chemical compound NCCCC[C@H](N)C(=O)NCC(=O)NCC(O)=O ISHNZELVUVPCHY-ZETCQYMHSA-N 0.000 description 2
- YBAFDPFAUTYYRW-UHFFFAOYSA-N N-L-alpha-glutamyl-L-leucine Natural products CC(C)CC(C(O)=O)NC(=O)C(N)CCC(O)=O YBAFDPFAUTYYRW-UHFFFAOYSA-N 0.000 description 2
- LSXGADJXBDFXQU-DLOVCJGASA-N Phe-Ala-Asp Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC1=CC=CC=C1 LSXGADJXBDFXQU-DLOVCJGASA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- SJRUJQFQVLMZFW-WPRPVWTQSA-N Val-Pro-Gly Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)NCC(O)=O SJRUJQFQVLMZFW-WPRPVWTQSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 108010076324 alanyl-glycyl-glycine Proteins 0.000 description 2
- 239000000883 anti-obesity agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 108010092854 aspartyllysine Proteins 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- VPZXBVLAVMBEQI-UHFFFAOYSA-N glycyl-DL-alpha-alanine Natural products OC(=O)C(C)NC(=O)CN VPZXBVLAVMBEQI-UHFFFAOYSA-N 0.000 description 2
- 108010089804 glycyl-threonine Proteins 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 108010005942 methionylglycine Proteins 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 108010070643 prolylglutamic acid Proteins 0.000 description 2
- 208000016261 weight loss Diseases 0.000 description 2
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- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 1
- BRPMXFSTKXXNHF-IUCAKERBSA-N (2s)-1-[2-[[(2s)-pyrrolidine-2-carbonyl]amino]acetyl]pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)CNC(=O)[C@H]1NCCC1 BRPMXFSTKXXNHF-IUCAKERBSA-N 0.000 description 1
- YLTKNGYYPIWKHZ-ACZMJKKPSA-N Ala-Ala-Glu Chemical compound C[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@H](C(O)=O)CCC(O)=O YLTKNGYYPIWKHZ-ACZMJKKPSA-N 0.000 description 1
- TTXMOJWKNRJWQJ-FXQIFTODSA-N Ala-Arg-Ser Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)C)CCCN=C(N)N TTXMOJWKNRJWQJ-FXQIFTODSA-N 0.000 description 1
- JYEBJTDTPNKQJG-FXQIFTODSA-N Ala-Asn-Met Chemical compound C[C@@H](C(=O)N[C@@H](CC(=O)N)C(=O)N[C@@H](CCSC)C(=O)O)N JYEBJTDTPNKQJG-FXQIFTODSA-N 0.000 description 1
- ZIBWKCRKNFYTPT-ZKWXMUAHSA-N Ala-Asn-Val Chemical compound [H]N[C@@H](C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C(C)C)C(O)=O ZIBWKCRKNFYTPT-ZKWXMUAHSA-N 0.000 description 1
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Abstract
Description
RT(min) | Type | Width(min) | Area | Height | Area% |
12.431 | BB | 1.86 | 3001.36 | 142.52 | 99.06 |
15.684 | BBA | 0.79 | 28.40 | 1.48 | 0.94 |
Sum | 3029.76 |
RT(min) | Type | Width(min) | Area | Height | Area% |
12.410 | BB | 1.36 | 3062.49 | 145.21 | 100.00 |
Sum | 3062.49 |
RT(min) | Type | Width(min) | Area | Height | Area% |
6.189 | BBA | 0.52 | 2944.36 | 298.07 | 99.93 |
7.639 | BB | 0.30 | 2.00 | 0.23 | 0.07 |
Sum | 2946.336 |
Claims (22)
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CN202010015510.1A CN111154736B (zh) | 2020-01-07 | 2020-01-07 | 用于制备奥利司他中间体的方法 |
PCT/CN2021/070495 WO2021139689A1 (zh) | 2020-01-07 | 2021-01-06 | 一种生物酶用于制备奥利司他中间体的用途及制备方法 |
KR1020227027087A KR20220125300A (ko) | 2020-01-07 | 2021-01-06 | 오르리스타트 중간체 제조를 위한 생물학적 효소의 용도 및 제조 방법 |
JP2022541240A JP7498278B2 (ja) | 2020-01-07 | 2021-01-06 | オルリスタット中間体の製造における酵素の用途及び製造方法 |
EP21738086.4A EP4086343A4 (en) | 2020-01-07 | 2021-01-06 | USE OF A BIOLOGICAL ENZYME FOR THE PREPARATION OF AN ORLISTAT INTERMEDIATE AND PREPARATION METHOD |
BR112022013466A BR112022013466A2 (pt) | 2020-01-07 | 2021-01-06 | Uso de enzima biológica para preparar um intermediário de orlistate e método de preparo |
US17/790,787 US20240158819A1 (en) | 2020-01-07 | 2021-01-06 | Use of Biological Enzyme for Preparing Orlistat Intermediate, and Preparation Method |
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EP (1) | EP4086343A4 (zh) |
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KR (1) | KR20220125300A (zh) |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN109022473A (zh) * | 2018-08-13 | 2018-12-18 | 浙江海洋大学 | 一种酶法制备奥利司他中间体的方法 |
CN109097344A (zh) * | 2018-08-07 | 2018-12-28 | 浙江海洋大学 | 一种海洋新鞘脂菌短链醇脱氢酶突变体及其应用 |
WO2021139689A1 (zh) * | 2020-01-07 | 2021-07-15 | 植恩生物技术股份有限公司 | 一种生物酶用于制备奥利司他中间体的用途及制备方法 |
CN114854704A (zh) * | 2021-01-20 | 2022-08-05 | 合肥立方制药股份有限公司 | 一种用于制备奥利司他中间体的生物酶及其应用 |
CN115851642A (zh) * | 2022-09-14 | 2023-03-28 | 杭州鑫富科技有限公司 | 一种酮基泛解酸内酯还原酶及其应用 |
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- 2021-01-06 WO PCT/CN2021/070495 patent/WO2021139689A1/zh unknown
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CN109097344A (zh) * | 2018-08-07 | 2018-12-28 | 浙江海洋大学 | 一种海洋新鞘脂菌短链醇脱氢酶突变体及其应用 |
CN109097344B (zh) * | 2018-08-07 | 2021-10-22 | 浙江海洋大学 | 一种海洋新鞘脂菌短链醇脱氢酶突变体及其应用 |
CN109022473A (zh) * | 2018-08-13 | 2018-12-18 | 浙江海洋大学 | 一种酶法制备奥利司他中间体的方法 |
CN109022473B (zh) * | 2018-08-13 | 2021-09-17 | 浙江海洋大学 | 一种酶法制备奥利司他中间体的方法 |
WO2021139689A1 (zh) * | 2020-01-07 | 2021-07-15 | 植恩生物技术股份有限公司 | 一种生物酶用于制备奥利司他中间体的用途及制备方法 |
CN114854704A (zh) * | 2021-01-20 | 2022-08-05 | 合肥立方制药股份有限公司 | 一种用于制备奥利司他中间体的生物酶及其应用 |
CN114854704B (zh) * | 2021-01-20 | 2023-10-10 | 合肥大禹制药有限公司 | 一种用于制备奥利司他中间体的生物酶及其应用 |
CN115851642A (zh) * | 2022-09-14 | 2023-03-28 | 杭州鑫富科技有限公司 | 一种酮基泛解酸内酯还原酶及其应用 |
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EP4086343A4 (en) | 2024-07-03 |
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JP7498278B2 (ja) | 2024-06-11 |
EP4086343A1 (en) | 2022-11-09 |
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