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 |
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| GB0229443D0 (en) * | 2002-12-18 | 2003-01-22 | Avecia Ltd | Process |
| EP1660512A4 (en) * | 2003-06-02 | 2009-12-23 | Isis Pharmaceuticals Inc | SYNTHESIS OF OLIGONUCLEOTIDES USING ALTERNATIVE SOLVENTS |
| JP5956108B2 (ja) * | 2007-10-15 | 2016-07-20 | ハネウェル・インターナショナル・インコーポレーテッド | １，３，５−トリメチルヘキサヒドロ−１，３，５−トリアジンを含有しないｎ−メチルイミダゾールのキャッピング剤を用いたオリゴヌクレオチドまたはホスホロチオ酸オリゴヌクレオチドの合成 |
| WO2012059510A1 (en) * | 2010-11-02 | 2012-05-10 | Girindus America, Inc. | Back pressure control during solid-phase synthesis on polymeric supports |
| EP2885312B1 (en) * | 2012-08-15 | 2025-09-03 | Ionis Pharmaceuticals, Inc. | Method of preparing oligomeric compounds using modified capping protocols |
| TWI707038B (zh) | 2013-08-05 | 2020-10-11 | 美商扭轉生物科技有限公司 | 重新合成之基因庫 |
| WO2016126882A1 (en) | 2015-02-04 | 2016-08-11 | 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 |
| KR20180050411A (ko) | 2015-09-18 | 2018-05-14 | 트위스트 바이오사이언스 코포레이션 | 올리고핵산 변이체 라이브러리 및 그의 합성 |
| 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 |
| JP6854340B2 (ja) | 2016-08-22 | 2021-04-07 | ツイスト バイオサイエンス コーポレーション | デノボ合成された核酸ライブラリ |
| US10417457B2 (en) | 2016-09-21 | 2019-09-17 | Twist Bioscience Corporation | Nucleic acid based data storage |
| KR102514213B1 (ko) | 2016-12-16 | 2023-03-27 | 트위스트 바이오사이언스 코포레이션 | 면역 시냅스의 변이체 라이브러리 및 그의 합성 |
| CN110892485B (zh) | 2017-02-22 | 2024-03-22 | 特韦斯特生物科学公司 | 基于核酸的数据存储 |
| WO2018170169A1 (en) | 2017-03-15 | 2018-09-20 | Twist Bioscience Corporation | Variant libraries of the immunological synapse and synthesis thereof |
| WO2018231864A1 (en) | 2017-06-12 | 2018-12-20 | Twist Bioscience Corporation | Methods for seamless nucleic acid assembly |
| US10696965B2 (en) | 2017-06-12 | 2020-06-30 | Twist Bioscience Corporation | Methods for seamless nucleic acid assembly |
| CN111566125A (zh) | 2017-09-11 | 2020-08-21 | 特韦斯特生物科学公司 | Gpcr结合蛋白及其合成 |
| 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 |
| US12357959B2 (en) | 2018-12-26 | 2025-07-15 | Twist Bioscience Corporation | Highly accurate de novo polynucleotide synthesis |
| CA3131691A1 (en) | 2019-02-26 | 2020-09-03 | Twist Bioscience Corporation | Variant nucleic acid libraries for antibody optimization |
| 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 |
| AU2020298294A1 (en) | 2019-06-21 | 2022-02-17 | Twist Bioscience Corporation | Barcode-based nucleic acid sequence assembly |
| WO2021061842A1 (en) | 2019-09-23 | 2021-04-01 | Twist Bioscience Corporation | Variant nucleic acid libraries for single domain antibodies |
| JP2022548309A (ja) | 2019-09-23 | 2022-11-17 | ツイスト バイオサイエンス コーポレーション | Ｃｒｔｈ２のバリアント核酸ライブラリー |
| IL293670A (en) | 2019-12-09 | 2022-08-01 | Twist Bioscience Corp | Variable nucleic acid libraries for adenosine receptors |
| CN115362163B (zh) | 2020-04-14 | 2025-04-11 | 住友化学株式会社 | 核酸寡聚物的制造方法 |
| MX2023007242A (es) * | 2020-12-18 | 2023-06-29 | Lilly Co Eli | Sintetizador de oligonucleotidos de lecho fluidizado oscilante. |
| 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 WO PCT/GB2001/005338 patent/WO2002046205A2/en not_active Ceased
- 2001-12-03 CA CA2714353A patent/CA2714353A1/en not_active Abandoned
- 2001-12-03 EP EP10009705A patent/EP2332954A3/en not_active Withdrawn
- 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 CN CNB018201016A patent/CN1302005C/zh not_active Expired - Fee Related
- 2001-12-03 AU AU2002220870A patent/AU2002220870A1/en not_active Abandoned
- 2001-12-03 CA CA2437040A patent/CA2437040C/en not_active Expired - Lifetime
-
2003
- 2003-06-05 US US10/454,841 patent/US7227017B2/en not_active Expired - Lifetime
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