CA2370478A1 - N-acylphosphoramidites and their use in oligonucleotide synthesis - Google Patents
N-acylphosphoramidites and their use in oligonucleotide synthesis Download PDFInfo
- Publication number
- CA2370478A1 CA2370478A1 CA002370478A CA2370478A CA2370478A1 CA 2370478 A1 CA2370478 A1 CA 2370478A1 CA 002370478 A CA002370478 A CA 002370478A CA 2370478 A CA2370478 A CA 2370478A CA 2370478 A1 CA2370478 A1 CA 2370478A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- different
- group
- same
- halogen
- 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.)
- Abandoned
Links
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric 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
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12586799P | 1999-03-24 | 1999-03-24 | |
US60/125,867 | 1999-03-24 | ||
PCT/US2000/004032 WO2000056749A1 (en) | 1999-03-24 | 2000-02-16 | N-acylphosphoramidites and their use in oligonucleotide synthesis |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2370478A1 true CA2370478A1 (en) | 2000-09-28 |
Family
ID=22421815
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002370478A Abandoned CA2370478A1 (en) | 1999-03-24 | 2000-02-16 | N-acylphosphoramidites and their use in oligonucleotide synthesis |
Country Status (5)
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2998800A (en) | 1999-03-24 | 2000-10-09 | Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, The | N-acylphosphoramidites and their use in oligonucleotide synthesis |
US7355037B2 (en) | 2001-12-03 | 2008-04-08 | The United States Of America As Represented By The Department Of Health And Human Services | Thermolabile hydroxyl protecting groups and methods of use |
EP1519938B1 (en) * | 2002-06-27 | 2007-04-11 | F. Hoffmann-La Roche Ag | Synthesis of purine derivatives |
WO2004101582A2 (en) | 2003-05-09 | 2004-11-25 | Government Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Thermolabile hydroxyl protecting groups and methods of use |
JP4865544B2 (ja) * | 2004-03-25 | 2012-02-01 | 株式会社キラルジェン | 立体規則性の高いリボヌクレオチド類縁体及びデオキシリボヌクレオチド類縁体の製造法 |
WO2006065751A2 (en) | 2004-12-13 | 2006-06-22 | Government Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Cpg oligonucleotide prodrugs, compositions thereof and associated therapeutic methods |
JP5558811B2 (ja) * | 2006-06-01 | 2014-07-23 | トリリンク バイオテクノロジーズ | 核酸増幅のための化学的に修飾されたオリゴヌクレオチドプライマー |
US7902345B2 (en) | 2006-12-05 | 2011-03-08 | Sequenom, Inc. | Detection and quantification of biomolecules using mass spectrometry |
WO2009032781A2 (en) | 2007-08-29 | 2009-03-12 | Sequenom, Inc. | Methods and compositions for universal size-specific polymerase chain reaction |
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 |
US8039612B2 (en) * | 2007-10-15 | 2011-10-18 | Honeywell International, Inc. | Synthesis of oligonucleotides or phosphorothioate oligonucleotide with a capping agent of N-methylimidazole free of 1,3,5-trimethylhexahydro-1,3,5-triazine |
CA2725239C (en) | 2008-05-27 | 2019-02-26 | Trilink Biotechnologies | Chemically modified nucleoside 5'-triphosphates for thermally initiated amplification of nucleic acid |
EP2408936A4 (en) * | 2009-03-18 | 2013-01-30 | Sequenom Inc | USE OF HEAT-STAINED ENDONUCLEASES FOR THE PREPARATION OF REPORTER MOLECULES |
US9631227B2 (en) | 2009-07-06 | 2017-04-25 | Trilink Biotechnologies, Inc. | Chemically modified ligase cofactors, donors and acceptors |
ES2521740T3 (es) * | 2009-07-06 | 2014-11-13 | Trilink Biotechnologies | Cofactores, dadores y aceptores de ligasa modificados químicamente |
US9556124B2 (en) | 2013-10-31 | 2017-01-31 | Honeywell International Inc. | Methods for removing triazine from N-methylimidazole for synthesis of oligonucleotide |
CN113584020A (zh) | 2015-09-21 | 2021-11-02 | 垂林克生物技术公司 | 用于合成5’-加帽rna的组合物和方法 |
US20230271998A1 (en) | 2020-06-30 | 2023-08-31 | United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Solid support for synthesizing nucleic acid sequences and methods for making and using |
WO2023147352A1 (en) | 2022-01-27 | 2023-08-03 | Trilink Biotechnologies, Llc | Trinucleotide cap analogs and methods of use thereof |
Family Cites Families (68)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3534017A (en) | 1967-03-14 | 1970-10-13 | Kyowa Hakko Kogyo Kk | Process for the preparation of nucleoside-5'-diphosphates and triphosphates and mono- and oligo-nucleotidyl-nucleoside-5'-diphosphates and triphosphates |
DE2826622A1 (de) | 1978-06-19 | 1980-01-03 | Hoechst Ag | Verfahren zur herstellung von 3-acyl- 2-alkyl- und 3-acyl-2-aryl-1.3.2-benzoxazaphospholanen sowie einige spezielle dieser verbindungen |
US4458066A (en) | 1980-02-29 | 1984-07-03 | University Patents, Inc. | Process for preparing polynucleotides |
US4415732A (en) | 1981-03-27 | 1983-11-15 | University Patents, Inc. | Phosphoramidite compounds and processes |
US4973679A (en) | 1981-03-27 | 1990-11-27 | University Patents, Inc. | Process for oligonucleo tide synthesis using phosphormidite intermediates |
US4668777A (en) | 1981-03-27 | 1987-05-26 | University Patents, Inc. | Phosphoramidite nucleoside compounds |
US4417046A (en) | 1981-08-24 | 1983-11-22 | Eli Lilly And Company | Process for isolating oligonucleotide product from a coupling reaction mixture |
EP0090789A1 (en) | 1982-03-26 | 1983-10-05 | Monsanto Company | Chemical DNA synthesis |
US4816570A (en) | 1982-11-30 | 1989-03-28 | The Board Of Regents Of The University Of Texas System | Biologically reversible phosphate and phosphonate protective groups |
US4663446A (en) | 1983-06-27 | 1987-05-05 | Trustees Of The Univ. Of Massachusetts | N2 (phenyl substituted) deoxy guanosine containing compounds |
USRE34069E (en) | 1983-08-18 | 1992-09-15 | Biosyntech Gmbh | Process for the preparation of oligonucleotides |
DE3329892A1 (de) | 1983-08-18 | 1985-03-07 | Köster, Hubert, Prof. Dr., 2000 Hamburg | Verfahren zur herstellung von oligonucleotiden |
US5166330A (en) | 1983-09-06 | 1992-11-24 | Hoechst Aktiengesellschaft | Process for the preparation of nucleoside alkyl-aralkyl- and aryl-phosphonites and -phosphonates |
FR2556726B1 (fr) | 1983-12-20 | 1987-02-20 | California Inst Of Techn | Compositions a base d'oligonucleotides monocatenaires et procede pour leur preparation |
US4849513A (en) | 1983-12-20 | 1989-07-18 | California Institute Of Technology | Deoxyribonucleoside phosphoramidites in which an aliphatic amino group is attached to the sugar ring and their use for the preparation of oligonucleotides containing aliphatic amino groups |
JPS61112093A (ja) | 1984-11-05 | 1986-05-30 | Wakunaga Seiyaku Kk | ヌクレオチド誘導体 |
FR2575751B1 (fr) | 1985-01-08 | 1987-04-03 | Pasteur Institut | Nouveaux nucleosides de derives de l'adenosine, leur preparation et leurs applications biologiques |
DE3507881A1 (de) | 1985-03-06 | 1986-09-11 | Hoechst Ag, 6230 Frankfurt | Verfahren und mittel zur phosphorylierung |
US5252760A (en) | 1985-03-28 | 1993-10-12 | Chiron Corporation | Method of using colored phosphorylating reagents |
JPH0829090B2 (ja) | 1985-03-28 | 1996-03-27 | チロン コ−ポレイシヨン | ポリヌクレオチドの製造方法 |
US5332845A (en) | 1985-03-28 | 1994-07-26 | Chiron Corporation | Phosphorylating reagents |
US4739044A (en) | 1985-06-13 | 1988-04-19 | Amgen | Method for derivitization of polynucleotides |
US4757141A (en) | 1985-08-26 | 1988-07-12 | Applied Biosystems, Incorporated | Amino-derivatized phosphite and phosphate linking agents, phosphoramidite precursors, and useful conjugates thereof |
US5258538A (en) | 1985-08-26 | 1993-11-02 | Applied Biosystems, Inc. | 2,3-disubstituted-1,3,2-oxazaphosphacycloalkanes as nucleic acid linking agents |
EP0216357A3 (en) | 1985-09-25 | 1988-08-31 | Nippon Zeon Co., Ltd. | Phosphoramidite compounds and process for production thereof |
US4959463A (en) | 1985-10-15 | 1990-09-25 | Genentech, Inc. | Intermediates |
US4808708A (en) | 1985-11-02 | 1989-02-28 | Toagosei Chemical Industry Co., Ltd. | Phosphorsulfide derivatives of deoxynucleosides or deoxynucleotides and their uses |
FR2596761B1 (fr) | 1986-04-08 | 1988-05-20 | Commissariat Energie Atomique | Derives de nucleosides et leur utilisation pour la synthese d'oligonucleotides |
US5091519A (en) | 1986-05-01 | 1992-02-25 | Amoco Corporation | Nucleotide compositions with linking groups |
DE3751468T2 (de) | 1986-10-30 | 1996-02-29 | Daicel Chem | Verfahren zur herstellung von oligonukleotiden und verbindungen zur bildung hochmolekularer schutzgruppen. |
US5071974A (en) | 1986-10-31 | 1991-12-10 | Amoco Corporation | Compositions and methods for the synthesis of oligonucleotides having 5'-phosphorylated termini |
US4965349A (en) | 1987-12-24 | 1990-10-23 | Applied Biosystems, Inc. | Method of synthesizing oligonucleotides labeled with ammonia-labile groups on solid phase supports |
US5449602A (en) | 1988-01-13 | 1995-09-12 | Amoco Corporation | Template-directed photoligation |
WO1989009221A1 (en) | 1988-03-25 | 1989-10-05 | University Of Virginia Alumni Patents Foundation | Oligonucleotide n-alkylphosphoramidates |
US5324831A (en) | 1988-04-06 | 1994-06-28 | The United States Of America As Represented By The Secretary Of Health And Human Services | Phosphoramidite reagent for chemical synthesis of modified DNA |
JPH0291088A (ja) | 1988-09-29 | 1990-03-30 | Central Glass Co Ltd | ホスファイトおよびヌクレオシド‐3’‐ホスファイト誘導体およびこれを用いるオリゴヌクレオチドの合成法 |
DE3916871A1 (de) | 1989-05-24 | 1990-11-29 | Boehringer Mannheim Gmbh | Modifiziertes phosphoramidit-verfahren zur herstellung von modifizierten nukleinsaeuren |
US5744101A (en) | 1989-06-07 | 1998-04-28 | Affymax Technologies N.V. | Photolabile nucleoside protecting groups |
US5506351A (en) | 1992-07-23 | 1996-04-09 | Isis Pharmaceuticals | Process for the preparation of 2'-O-alkyl guanosine and related compounds |
US5646265A (en) | 1990-01-11 | 1997-07-08 | Isis Pharmceuticals, Inc. | Process for the preparation of 2'-O-alkyl purine phosphoramidites |
US5430138A (en) | 1990-07-27 | 1995-07-04 | Chiron Corporation | Hydroxyl-protecting groups attached to cytidine nucleotide compounds which are orthogonally removable |
US5525719A (en) | 1991-08-30 | 1996-06-11 | Chemgenes Corporation | N-protected-2'-O-methyl-and N-protected-3'-O-methyl-ribonucleosides and their phosphoramidite derivatives |
US5214135A (en) | 1991-08-30 | 1993-05-25 | Chemgenes Corporation | N-protected-2'-O-methyl-ribonucleosides and N-protected 2'-O-methyl-3'-cyanoethyl-N-,N-diisopropyl phosphoramidite ribonucleosides |
US5556961A (en) | 1991-11-15 | 1996-09-17 | Foote; Robert S. | Nucleosides with 5'-O-photolabile protecting groups |
WO1993010820A1 (en) | 1991-11-26 | 1993-06-10 | Gilead Sciences, Inc. | Enhanced triple-helix and double-helix formation with oligomers containing modified pyrimidines |
FR2685331A1 (fr) * | 1991-12-12 | 1993-06-25 | Centre Nat Rech Scient | Phosphotriesters de la ddu, leur preparation et leur application en therapeutique. |
US5348868A (en) | 1992-04-24 | 1994-09-20 | Beckman Instruments, Inc. | Methods and reagents for cleaving and deprotecting oligonucleotides |
US5616700A (en) | 1992-04-24 | 1997-04-01 | Beckman Instruments, Inc. | Processes for synthesizing nucleotides and modified nucleotides using N.sub. |
US5428148A (en) | 1992-04-24 | 1995-06-27 | Beckman Instruments, Inc. | N4 - acylated cytidinyl compounds useful in oligonucleotide synthesis |
GB9304618D0 (en) | 1993-03-06 | 1993-04-21 | Ciba Geigy Ag | Chemical compounds |
US6001982A (en) | 1993-07-29 | 1999-12-14 | Isis Pharmaceuticals, Inc. | Synthesis of oligonucleotides |
US5571902A (en) | 1993-07-29 | 1996-11-05 | Isis Pharmaceuticals, Inc. | Synthesis of oligonucleotides |
EP0644196B1 (de) | 1993-09-17 | 1997-11-05 | Novartis AG | TTTr als Schutzgruppe in der Nukleotidsynthese |
DE4343126A1 (de) | 1993-12-17 | 1995-06-22 | Hoechst Ag | Festphasensynthese von Oligoribonucleotiden |
US5623068A (en) | 1994-03-07 | 1997-04-22 | Beckman Instruments, Inc. | Synthesis of DNA using substituted phenylacetyl-protected nucleotides |
US5510476A (en) | 1994-07-07 | 1996-04-23 | Isis Pharmaceuticals, Inc. | Carbocation scavenging during oligonucleotide synthesis |
US5574146A (en) | 1994-08-30 | 1996-11-12 | Beckman Instruments, Inc. | Oligonucleotide synthesis with substituted aryl carboxylic acids as activators |
US5703223A (en) | 1994-09-02 | 1997-12-30 | Thomas Jefferson University | Solid phase synthesis of oligonucleotides with stereospecific substituted phosphonate linkages by pentavalent grignard coupling |
US5681940A (en) | 1994-11-02 | 1997-10-28 | Icn Pharmaceuticals | Sugar modified nucleosides and oligonucleotides |
DE4444996A1 (de) | 1994-12-16 | 1996-06-20 | Wolfgang Prof Dr Dr Pfleiderer | Nucleosid-Derivate mit photolabilen Schutzgruppen |
US5908926A (en) | 1995-03-16 | 1999-06-01 | Duke University | 5'to 3' nucleic acid synthesis using 3'-photoremovable protecting group |
US5614622A (en) | 1995-06-01 | 1997-03-25 | Hybridon, Inc. | 5-pentenoyl moiety as a nucleoside-amino protecting group, 4-pentenoyl-protected nucleotide synthons, and related oligonucleotide syntheses |
US5731429A (en) | 1995-10-18 | 1998-03-24 | Beckman Instruments, Inc. | Cac -methylphosphonamidites and methods for preparing methylphosphonates |
US5705621A (en) | 1995-11-17 | 1998-01-06 | Isis Pharmaceuticals, Inc. | Oligomeric phosphite, phosphodiester, Phosphorothioate and phosphorodithioate compounds and intermediates for preparing same |
US6022963A (en) | 1995-12-15 | 2000-02-08 | Affymetrix, Inc. | Synthesis of oligonucleotide arrays using photocleavable protecting groups |
ES2192672T3 (es) | 1996-11-18 | 2003-10-16 | Takeshi Imanishi | Nuevos analogos de nucleotidos. |
US5760209A (en) | 1997-03-03 | 1998-06-02 | Isis Pharmaceuticals, Inc. | Protecting group for synthesizing oligonucleotide analogs |
AU2998800A (en) | 1999-03-24 | 2000-10-09 | Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, The | N-acylphosphoramidites and their use in oligonucleotide synthesis |
-
2000
- 2000-02-16 AU AU29988/00A patent/AU2998800A/en not_active Abandoned
- 2000-02-16 WO PCT/US2000/004032 patent/WO2000056749A1/en not_active Application Discontinuation
- 2000-02-16 CA CA002370478A patent/CA2370478A1/en not_active Abandoned
- 2000-02-16 US US09/937,292 patent/US6965041B1/en not_active Expired - Lifetime
- 2000-02-16 EP EP00908691A patent/EP1163251A1/en not_active Withdrawn
-
2001
- 2001-02-23 US US09/792,799 patent/US6762298B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US6762298B2 (en) | 2004-07-13 |
US20010044529A1 (en) | 2001-11-22 |
AU2998800A (en) | 2000-10-09 |
US6965041B1 (en) | 2005-11-15 |
EP1163251A1 (en) | 2001-12-19 |
WO2000056749A1 (en) | 2000-09-28 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FZDE | Dead |