JP2004517089A5 - - Google Patents
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- Publication number
- JP2004517089A5 JP2004517089A5 JP2002547942A JP2002547942A JP2004517089A5 JP 2004517089 A5 JP2004517089 A5 JP 2004517089A5 JP 2002547942 A JP2002547942 A JP 2002547942A JP 2002547942 A JP2002547942 A JP 2002547942A JP 2004517089 A5 JP2004517089 A5 JP 2004517089A5
- Authority
- JP
- Japan
- Prior art keywords
- oligonucleotide
- solid support
- solvent
- acetonitrile
- cleaving
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 108091034117 Oligonucleotide Proteins 0.000 claims 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 24
- 238000000034 method Methods 0.000 claims 22
- 239000007787 solid Substances 0.000 claims 20
- 238000005406 washing Methods 0.000 claims 9
- 239000002904 solvent Substances 0.000 claims 8
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 4
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 230000002194 synthesizing effect Effects 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 claims 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 2
- 125000004492 methyl ester group Chemical group 0.000 claims 2
- 239000002777 nucleoside Substances 0.000 claims 2
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 2
- 150000003141 primary amines Chemical group 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 238000007605 air drying Methods 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- -1 alkyl diamine Chemical class 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 125000005233 alkylalcohol group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 239000012062 aqueous buffer Substances 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- ZCQGVFNHUATAJY-UHFFFAOYSA-N methyl 2-[methyl(prop-2-enoyl)amino]acetate Chemical compound COC(=O)CN(C)C(=O)C=C ZCQGVFNHUATAJY-UHFFFAOYSA-N 0.000 claims 1
- 229940017219 methyl propionate Drugs 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims 1
- AYGYHGXUJBFUJU-UHFFFAOYSA-N n-[2-(prop-2-enoylamino)ethyl]prop-2-enamide Chemical compound C=CC(=O)NCCNC(=O)C=C AYGYHGXUJBFUJU-UHFFFAOYSA-N 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0029610A GB0029610D0 (en) | 2000-12-05 | 2000-12-05 | Process |
| US09/740,031 US6768005B2 (en) | 2000-12-20 | 2000-12-20 | Process |
| PCT/GB2001/005338 WO2002046205A2 (en) | 2000-12-05 | 2001-12-03 | Process for the preparation of phosphorothionate oligonucleotides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004517089A JP2004517089A (ja) | 2004-06-10 |
| JP2004517089A5 true JP2004517089A5 (https=) | 2005-12-22 |
Family
ID=26245377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002547942A Pending JP2004517089A (ja) | 2000-12-05 | 2001-12-03 | ホスホロチオエートオリゴヌクレオチドの調製方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7227017B2 (https=) |
| EP (2) | EP2332954A3 (https=) |
| JP (1) | JP2004517089A (https=) |
| KR (1) | KR20040016826A (https=) |
| CN (1) | CN1302005C (https=) |
| AU (1) | AU2002220870A1 (https=) |
| CA (2) | CA2714353A1 (https=) |
| WO (1) | WO2002046205A2 (https=) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0229443D0 (en) * | 2002-12-18 | 2003-01-22 | Avecia Ltd | Process |
| WO2004108081A2 (en) * | 2003-06-02 | 2004-12-16 | Isis Pharmaceuticals, Inc. | Oligonucleotide synthesis with alternative solvents |
| EP2205619A4 (en) * | 2007-10-15 | 2013-04-17 | Honeywell Int Inc | SYNTHESIS OF OLIGONUCLEOTIDES OR A PHOSPHOROTHIOATE OLIGONUCLEOTIDE WITH A 1,3,5-TRIMETHYLHEXAHYDRO-1,3,5-TRIAZINE-FREE N-METHYLIMIDAZOLE STRIPPING AGENT |
| WO2012059510A1 (en) * | 2010-11-02 | 2012-05-10 | Girindus America, Inc. | Back pressure control during solid-phase synthesis on polymeric supports |
| CN104736551B (zh) * | 2012-08-15 | 2017-07-28 | Ionis制药公司 | 使用改进的封端方案制备寡聚化合物的方法 |
| SG11201600853UA (en) | 2013-08-05 | 2016-03-30 | Twist Bioscience Corp | De novo synthesized gene libraries |
| US10669304B2 (en) | 2015-02-04 | 2020-06-02 | Twist Bioscience Corporation | Methods and devices for de novo oligonucleic acid assembly |
| US9981239B2 (en) | 2015-04-21 | 2018-05-29 | Twist Bioscience Corporation | Devices and methods for oligonucleic acid library synthesis |
| EP3350314A4 (en) | 2015-09-18 | 2019-02-06 | Twist Bioscience Corporation | OLIGONUCLEIC ACID VARIANT LIBRARIES VARIANT AND SYNTHESIS THEREOF |
| KR102794025B1 (ko) | 2015-09-22 | 2025-04-09 | 트위스트 바이오사이언스 코포레이션 | 핵산 합성을 위한 가요성 기판 |
| CN115920796A (zh) | 2015-12-01 | 2023-04-07 | 特韦斯特生物科学公司 | 功能化表面及其制备 |
| EP3500672A4 (en) | 2016-08-22 | 2020-05-20 | Twist Bioscience Corporation | DE NOVO SYNTHETIZED NUCLEIC ACID LIBRARIES |
| US10417457B2 (en) | 2016-09-21 | 2019-09-17 | Twist Bioscience Corporation | Nucleic acid based data storage |
| GB2573069A (en) | 2016-12-16 | 2019-10-23 | Twist Bioscience Corp | Variant libraries of the immunological synapse and synthesis thereof |
| EP4556433A3 (en) | 2017-02-22 | 2025-08-06 | Twist Bioscience Corporation | Nucleic acid based data storage |
| WO2018170169A1 (en) | 2017-03-15 | 2018-09-20 | Twist Bioscience Corporation | Variant libraries of the immunological synapse and synthesis thereof |
| WO2018231872A1 (en) | 2017-06-12 | 2018-12-20 | Twist Bioscience Corporation | Methods for seamless nucleic acid assembly |
| WO2018231864A1 (en) | 2017-06-12 | 2018-12-20 | Twist Bioscience Corporation | Methods for seamless nucleic acid assembly |
| US11407837B2 (en) | 2017-09-11 | 2022-08-09 | Twist Bioscience Corporation | GPCR binding proteins and synthesis thereof |
| CN111565834B (zh) | 2017-10-20 | 2022-08-26 | 特韦斯特生物科学公司 | 用于多核苷酸合成的加热的纳米孔 |
| CN109956987B (zh) * | 2017-12-14 | 2022-05-17 | 南京金斯瑞生物科技有限公司 | 氨解方法及氨解组合物 |
| KR102804057B1 (ko) | 2018-01-04 | 2025-05-07 | 트위스트 바이오사이언스 코포레이션 | Dna 기반 디지털 정보 저장 |
| CA3100739A1 (en) | 2018-05-18 | 2019-11-21 | Twist Bioscience Corporation | Polynucleotides, reagents, and methods for nucleic acid hybridization |
| WO2020139871A1 (en) | 2018-12-26 | 2020-07-02 | Twist Bioscience Corporation | Highly accurate de novo polynucleotide synthesis |
| CN113766930B (zh) | 2019-02-26 | 2025-07-22 | 特韦斯特生物科学公司 | Glp1受体的变异核酸文库 |
| JP2022522668A (ja) | 2019-02-26 | 2022-04-20 | ツイスト バイオサイエンス コーポレーション | 抗体を最適化するための変異体核酸ライブラリ |
| US11332738B2 (en) | 2019-06-21 | 2022-05-17 | Twist Bioscience Corporation | Barcode-based nucleic acid sequence assembly |
| JP2022548783A (ja) | 2019-09-23 | 2022-11-21 | ツイスト バイオサイエンス コーポレーション | 単一ドメイン抗体のバリアント核酸ライブラリー |
| EP4034566A4 (en) | 2019-09-23 | 2024-01-24 | Twist Bioscience Corporation | VARIANT NUCLEIC ACID BANKS FOR CRTH2 |
| BR112022011235A2 (pt) | 2019-12-09 | 2022-12-13 | Twist Bioscience Corp | Bibliotecas de variantes de ácido nucleico para receptores de adenosina |
| DK4137500T3 (da) | 2020-04-14 | 2026-04-20 | Sumitomo Chemical Co | Fremgangsmåde til fremstilling af nukleinsyreoligomer |
| KR20230119197A (ko) * | 2020-12-18 | 2023-08-16 | 일라이 릴리 앤드 캄파니 | 진동 유동층 올리고뉴클레오티드 합성기 |
| CN114573652B (zh) * | 2022-03-15 | 2025-02-07 | 安徽瑞拜药业有限公司 | 药用核酸合成工艺 |
| CN116854754B (zh) | 2023-09-01 | 2023-12-12 | 北京悦康科创医药科技股份有限公司 | 一种含有核糖环或其衍生结构的GalNAc化合物及其寡核苷酸缀合物 |
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-
2001
- 2001-12-03 CA CA2714353A patent/CA2714353A1/en not_active Abandoned
- 2001-12-03 CN CNB018201016A patent/CN1302005C/zh not_active Expired - Fee Related
- 2001-12-03 WO PCT/GB2001/005338 patent/WO2002046205A2/en not_active Ceased
- 2001-12-03 EP EP10009705A patent/EP2332954A3/en not_active Withdrawn
- 2001-12-03 CA CA2437040A patent/CA2437040C/en not_active Expired - Lifetime
- 2001-12-03 KR KR10-2003-7007445A patent/KR20040016826A/ko not_active Abandoned
- 2001-12-03 EP EP01999571A patent/EP1343802B1/en not_active Expired - Lifetime
- 2001-12-03 JP JP2002547942A patent/JP2004517089A/ja active Pending
- 2001-12-03 AU AU2002220870A patent/AU2002220870A1/en not_active Abandoned
-
2003
- 2003-06-05 US US10/454,841 patent/US7227017B2/en not_active Expired - Lifetime
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