CA2361079C - Method for deprotecting oligonucleotides - Google Patents
Method for deprotecting oligonucleotides Download PDFInfo
- Publication number
- CA2361079C CA2361079C CA2361079A CA2361079A CA2361079C CA 2361079 C CA2361079 C CA 2361079C CA 2361079 A CA2361079 A CA 2361079A CA 2361079 A CA2361079 A CA 2361079A CA 2361079 C CA2361079 C CA 2361079C
- Authority
- CA
- Canada
- Prior art keywords
- oligonucleotide
- substrate
- phosphate protecting
- reagent
- protecting groups
- 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.)
- Expired - Fee Related
Links
- 108091034117 Oligonucleotide Proteins 0.000 title claims abstract description 150
- 238000000034 method Methods 0.000 title claims abstract description 40
- 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 title description 39
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
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- 239000011368 organic material Substances 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000004713 phosphodiesters Chemical class 0.000 claims 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 claims 1
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- 239000012535 impurity Substances 0.000 description 18
- 238000010511 deprotection reaction Methods 0.000 description 16
- 239000002777 nucleoside Substances 0.000 description 14
- -1 Phosphate triester Chemical class 0.000 description 13
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- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 8
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- 229910019142 PO4 Inorganic materials 0.000 description 6
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- 238000012360 testing method Methods 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 150000003538 tetroses Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 229940113082 thymine Drugs 0.000 description 1
- 229960003087 tioguanine Drugs 0.000 description 1
- 150000003641 trioses Chemical class 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11857599P | 1999-02-05 | 1999-02-05 | |
| US60/118,575 | 1999-02-05 | ||
| PCT/US2000/002845 WO2000046231A1 (en) | 1999-02-05 | 2000-02-05 | Method for deprotecting oligonucleotides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2361079A1 CA2361079A1 (en) | 2000-08-10 |
| CA2361079C true CA2361079C (en) | 2010-05-25 |
Family
ID=22379444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2361079A Expired - Fee Related CA2361079C (en) | 1999-02-05 | 2000-02-05 | Method for deprotecting oligonucleotides |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6887990B1 (https=) |
| EP (1) | EP1149109B1 (https=) |
| JP (1) | JP4705716B2 (https=) |
| AT (1) | ATE443071T1 (https=) |
| AU (1) | AU767509B2 (https=) |
| CA (1) | CA2361079C (https=) |
| DE (1) | DE60042962D1 (https=) |
| DK (1) | DK1149109T3 (https=) |
| NO (1) | NO20013804L (https=) |
| WO (1) | WO2000046231A1 (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999041007A2 (en) | 1998-02-11 | 1999-08-19 | University Of Houston | Method and apparatus for chemical and biochemical reactions using photo-generated reagents |
| US6465628B1 (en) | 1999-02-04 | 2002-10-15 | Isis Pharmaceuticals, Inc. | Process for the synthesis of oligomeric compounds |
| CA2714353A1 (en) | 2000-12-05 | 2002-06-13 | Avecia Biotechnology Inc | Process for the preparation of phosphorothioate oligonucleotides |
| US6768005B2 (en) | 2000-12-20 | 2004-07-27 | Avecia Limited | Process |
| ATE312841T1 (de) | 2001-03-08 | 2005-12-15 | Applera Corp | Verfahren zum entschützen von oligonukleotide |
| US7211654B2 (en) | 2001-03-14 | 2007-05-01 | Regents Of The University Of Michigan | Linkers and co-coupling agents for optimization of oligonucleotide synthesis and purification on solid supports |
| US20030153741A1 (en) * | 2002-02-08 | 2003-08-14 | Marek Kwiatkowski | Methods for separating oligonucleotides |
| US8138330B2 (en) * | 2006-09-11 | 2012-03-20 | Sigma-Aldrich Co. Llc | Process for the synthesis of oligonucleotides |
| CA2721969C (en) * | 2008-04-24 | 2016-06-07 | Girindus America, Inc. | Process for the manufacture of oligonucleotides |
| JPWO2021045141A1 (https=) * | 2019-09-04 | 2021-03-11 | ||
| JP7640461B2 (ja) | 2019-10-11 | 2025-03-05 | 住友化学株式会社 | 核酸オリゴマーの製造方法 |
| JP7667788B2 (ja) | 2020-01-29 | 2025-04-23 | 住友化学株式会社 | 核酸オリゴマーの製造方法 |
| EP4098655A4 (en) | 2020-01-29 | 2024-02-28 | Sumitomo Chemical Company, Limited | METHOD FOR PRODUCING NUCLEIC ACID OLIGOMERS |
| EP4130018A4 (en) | 2020-03-27 | 2024-04-17 | Sumitomo Chemical Company, Limited | METHOD FOR PRODUCING A NUCLEIC ACID OLIGOMER |
| CN115867559A (zh) | 2020-07-09 | 2023-03-28 | 住友化学株式会社 | 核酸寡聚物的制造方法 |
| KR20230074205A (ko) | 2020-09-24 | 2023-05-26 | 스미또모 가가꾸 가부시끼가이샤 | 핵산 올리고머의 제조 방법 |
| CN117980285A (zh) | 2021-09-28 | 2024-05-03 | 住友化学株式会社 | 纯化二氯乙酸的制造方法 |
| EP4201947A1 (en) | 2021-12-22 | 2023-06-28 | F. Hoffmann-La Roche AG | Process for the backbone deprotection of oligonucleotides containing a terminal alkyl phosphonate group |
| 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 |
| US12509485B2 (en) | 2022-03-23 | 2025-12-30 | Sumitomo Chemical Company, Limited | Method for producing nucleic acid oligomer |
| EP4559925A1 (en) | 2022-07-22 | 2025-05-28 | Sumitomo Chemical Company, Limited | Production method of oligonucleotide |
| JPWO2024024873A1 (https=) | 2022-07-28 | 2024-02-01 | ||
| CN119855824A (zh) * | 2022-09-07 | 2025-04-18 | 株式会社日本触媒 | 核酸的制造方法、杂质的去除方法以及杂质少的核酸 |
| WO2024089953A1 (ja) | 2022-10-27 | 2024-05-02 | 住友化学株式会社 | オリゴヌクレオチドの製造方法 |
| US12415172B2 (en) | 2022-12-22 | 2025-09-16 | Synthego Corporation | Systems and method for automated oligonucleotide synthesis |
| JPWO2024143276A1 (https=) | 2022-12-26 | 2024-07-04 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4426517A (en) * | 1981-08-24 | 1984-01-17 | Eli Lilly And Company | Process for de-cyanoethylating blocked nucleotides |
| US4417046A (en) * | 1981-08-24 | 1983-11-22 | Eli Lilly And Company | Process for isolating oligonucleotide product from a coupling reaction mixture |
| FR2540122B1 (fr) * | 1983-01-27 | 1985-11-29 | Centre Nat Rech Scient | Nouveaux composes comportant une sequence d'oligonucleotide liee a un agent d'intercalation, leur procede de synthese et leur application |
| US5362866A (en) * | 1983-09-02 | 1994-11-08 | Molecular Biosystems, Inc. | Oligonucleotide polymeric support system with an oxidation cleavable link |
| WO1985001051A1 (en) * | 1983-09-02 | 1985-03-14 | Molecular Biosystems, Inc. | Oligonucleotide polymeric support system |
| US4672110A (en) * | 1983-11-29 | 1987-06-09 | Northwestern University | Method of deprotecting polynucleotide trimethylethyl phosphotriesters |
| JPS6242997A (ja) * | 1985-08-19 | 1987-02-24 | Akira Kaji | ヌクレオシドアルキルホスホネイトの製造方法 |
| SE9003743D0 (sv) | 1990-11-26 | 1990-11-26 | Pharmacia Ab | Method and means for oligonucleotide synthesis |
| DE19627898A1 (de) * | 1996-07-11 | 1998-01-15 | Hoechst Ag | Festphasensynthese von Oligonucleotiden |
| US6127533A (en) * | 1997-02-14 | 2000-10-03 | Isis Pharmaceuticals, Inc. | 2'-O-aminooxy-modified oligonucleotides |
| US6465628B1 (en) * | 1999-02-04 | 2002-10-15 | Isis Pharmaceuticals, Inc. | Process for the synthesis of oligomeric compounds |
-
2000
- 2000-02-05 US US09/498,773 patent/US6887990B1/en not_active Expired - Lifetime
- 2000-02-05 AT AT00907140T patent/ATE443071T1/de not_active IP Right Cessation
- 2000-02-05 DK DK00907140T patent/DK1149109T3/da active
- 2000-02-05 CA CA2361079A patent/CA2361079C/en not_active Expired - Fee Related
- 2000-02-05 JP JP2000597301A patent/JP4705716B2/ja not_active Expired - Lifetime
- 2000-02-05 WO PCT/US2000/002845 patent/WO2000046231A1/en not_active Ceased
- 2000-02-05 EP EP00907140A patent/EP1149109B1/en not_active Expired - Lifetime
- 2000-02-05 DE DE60042962T patent/DE60042962D1/de not_active Expired - Lifetime
- 2000-02-05 AU AU28687/00A patent/AU767509B2/en not_active Ceased
-
2001
- 2001-08-03 NO NO20013804A patent/NO20013804L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU767509B2 (en) | 2003-11-13 |
| NO20013804L (no) | 2001-08-22 |
| US6887990B1 (en) | 2005-05-03 |
| WO2000046231A1 (en) | 2000-08-10 |
| EP1149109A1 (en) | 2001-10-31 |
| DK1149109T3 (da) | 2010-01-11 |
| ATE443071T1 (de) | 2009-10-15 |
| JP2002536381A (ja) | 2002-10-29 |
| EP1149109B1 (en) | 2009-09-16 |
| JP4705716B2 (ja) | 2011-06-22 |
| AU2868700A (en) | 2000-08-25 |
| DE60042962D1 (de) | 2009-10-29 |
| NO20013804D0 (no) | 2001-08-03 |
| CA2361079A1 (en) | 2000-08-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150205 |