JP6333297B2 - 修飾ヌクレオシドまたは修飾ヌクレオチド - Google Patents
修飾ヌクレオシドまたは修飾ヌクレオチド Download PDFInfo
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- JP6333297B2 JP6333297B2 JP2015561957A JP2015561957A JP6333297B2 JP 6333297 B2 JP6333297 B2 JP 6333297B2 JP 2015561957 A JP2015561957 A JP 2015561957A JP 2015561957 A JP2015561957 A JP 2015561957A JP 6333297 B2 JP6333297 B2 JP 6333297B2
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- Prior art keywords
- modified
- molecule
- modified nucleotide
- nucleotide
- nucleoside
- 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.)
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- 125000003729 nucleotide group Chemical class 0.000 title claims description 158
- 239000002777 nucleoside Substances 0.000 title claims description 68
- 150000003833 nucleoside derivatives Chemical class 0.000 title claims description 61
- 239000002773 nucleotide Substances 0.000 claims description 75
- 125000006239 protecting group Chemical group 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 51
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 238000012163 sequencing technique Methods 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 108091033319 polynucleotide Proteins 0.000 claims description 22
- 102000040430 polynucleotide Human genes 0.000 claims description 22
- 239000002157 polynucleotide Substances 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 238000010348 incorporation Methods 0.000 claims description 19
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 18
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 17
- 125000003835 nucleoside group Chemical group 0.000 claims description 14
- 150000002431 hydrogen Chemical group 0.000 claims description 13
- 230000000295 complement effect Effects 0.000 claims description 12
- 238000010511 deprotection reaction Methods 0.000 claims description 11
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 10
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 9
- 102000004190 Enzymes Human genes 0.000 claims description 8
- 108090000790 Enzymes Proteins 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- JMXMXKRNIYCNRV-UHFFFAOYSA-N bis(hydroxymethyl)phosphanylmethanol Chemical group OCP(CO)CO JMXMXKRNIYCNRV-UHFFFAOYSA-N 0.000 claims description 7
- ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 claims description 6
- 108020004635 Complementary DNA Proteins 0.000 claims description 6
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 5
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 5
- 239000000872 buffer Substances 0.000 claims description 5
- 238000012544 monitoring process Methods 0.000 claims description 5
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 4
- 238000012986 modification Methods 0.000 claims description 4
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- 108010008286 DNA nucleotidylexotransferase Proteins 0.000 claims description 3
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- -1 modified nucleotide phosphoramidites Chemical class 0.000 description 48
- 125000005647 linker group Chemical group 0.000 description 43
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- 239000002585 base Substances 0.000 description 33
- 125000003118 aryl group Chemical group 0.000 description 24
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- 125000001072 heteroaryl group Chemical group 0.000 description 21
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- 239000000975 dye Substances 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- 125000004429 atom Chemical group 0.000 description 13
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- 125000000753 cycloalkyl group Chemical group 0.000 description 12
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- 238000001514 detection method Methods 0.000 description 11
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- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 10
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- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
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- 230000007017 scission Effects 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 235000011178 triphosphate Nutrition 0.000 description 8
- 239000003039 volatile agent Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000003491 array Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 230000000670 limiting effect Effects 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000012175 pyrosequencing Methods 0.000 description 5
- 230000002441 reversible effect Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 229940104302 cytosine Drugs 0.000 description 4
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 4
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- 125000003107 substituted aryl group Chemical group 0.000 description 4
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
- C12Q1/6869—Methods for sequencing
-
- 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
- C07H19/073—Pyrimidine radicals with 2-deoxyribosyl as the saccharide radical
-
- 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
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- 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
- C07H19/14—Pyrrolo-pyrimidine radicals
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- 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
- C07H19/173—Purine radicals with 2-deoxyribosyl as the saccharide radical
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- 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
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
- C12Q1/6876—Nucleic acid products used in the analysis of nucleic acids, e.g. primers or probes
-
- 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
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- Chemical & Material Sciences (AREA)
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- Biotechnology (AREA)
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- Genetics & Genomics (AREA)
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Families Citing this family (78)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0129012D0 (en) | 2001-12-04 | 2002-01-23 | Solexa Ltd | Labelled nucleotides |
| ES2550513T3 (es) | 2002-08-23 | 2015-11-10 | Illumina Cambridge Limited | Nucleótidos modificados para secuenciación de polinucleótidos |
| US11008359B2 (en) | 2002-08-23 | 2021-05-18 | Illumina Cambridge Limited | Labelled nucleotides |
| US7414116B2 (en) | 2002-08-23 | 2008-08-19 | Illumina Cambridge Limited | Labelled nucleotides |
| KR102230831B1 (ko) | 2013-03-15 | 2021-03-22 | 일루미나 케임브리지 리미티드 | 변형된 뉴클레오사이드 또는 뉴클레오타이드 |
| CN107074904B (zh) | 2014-10-23 | 2022-12-23 | 深圳华大智造科技股份有限公司 | 信号约束测序(scs)和用于信号约束测序的核苷酸类似物 |
| LT3212684T (lt) * | 2014-10-31 | 2020-04-10 | Illumina Cambridge Limited | Polimerai ir dnr kopolimero dangos |
| EP3356381A4 (en) | 2015-09-28 | 2019-06-12 | The Trustees of Columbia University in the City of New York | DESIGN AND SYNTHESIS OF NUCLEOTIDES BASED ON NOVEL DISULFIDE COMPOUNDS AS REVERSIBLE TERMINATORS FOR DNA SEQUENCING BY SYNTHESIS |
| US11266673B2 (en) | 2016-05-23 | 2022-03-08 | The Trustees Of Columbia University In The City Of New York | Nucleotide derivatives and methods of use thereof |
| US10385214B2 (en) | 2016-09-30 | 2019-08-20 | Illumina Cambridge Limited | Fluorescent dyes and their uses as biomarkers |
| WO2018107350A1 (zh) * | 2016-12-13 | 2018-06-21 | 深圳华大基因研究院 | 提纯可逆阻断脱氧核糖核苷三磷酸的方法和测序方法 |
| WO2018114710A1 (en) | 2016-12-22 | 2018-06-28 | Illumina Cambridge Limited | Coumarin compounds and their uses as fluorescent labels |
| CN108239669B (zh) * | 2016-12-23 | 2021-03-16 | 深圳华大智造科技股份有限公司 | 检测可逆性阻断dNTP中非阻断杂质含量的方法和试剂盒 |
| US11591647B2 (en) | 2017-03-06 | 2023-02-28 | Singular Genomics Systems, Inc. | Nucleic acid sequencing-by-synthesis (SBS) methods that combine SBS cycle steps |
| CN119639879A (zh) | 2017-03-28 | 2025-03-18 | 哥伦比亚大学董事会 | 用于连接荧光标记与用于dna合成测序的碱基的具有不同可裂解连接子的3'-o-改性的核苷酸类似物 |
| EP3913053A1 (en) | 2017-04-23 | 2021-11-24 | Illumina Cambridge Limited | Compositions and methods for improving sample identification in indexed nucleic acid libraries |
| SG11201909916YA (en) | 2017-04-23 | 2019-11-28 | Illumina Cambridge Ltd | Compositions and methods for improving sample identification in indexed nucleic acid libraries |
| WO2018200386A1 (en) | 2017-04-23 | 2018-11-01 | Illumina, Inc. | Compositions and methods for improving sample identification in indexed nucleic acid libraries |
| ES2941083T3 (es) | 2017-08-01 | 2023-05-16 | Mgi Tech Co Ltd | Método de secuenciación de ácidos nucleicos |
| GB201716931D0 (en) | 2017-10-16 | 2017-11-29 | Illumina Cambridge Ltd | New fluorescent compounds and their use as biomarkers |
| US12215124B2 (en) | 2018-02-21 | 2025-02-04 | Singular Genomics Systems, Inc. | Fluorinated nucleotides and uses thereof |
| US10755676B2 (en) | 2018-03-15 | 2020-08-25 | Magic Leap, Inc. | Image correction due to deformation of components of a viewing device |
| WO2019178393A1 (en) | 2018-03-15 | 2019-09-19 | The Trustees Of Columbia University In The City Of New York | Nucleotide analogues and use thereof for nucleic acid sequencing and analysis |
| JP7100069B2 (ja) | 2018-05-15 | 2022-07-12 | イルミナ インコーポレイテッド | 表面結合オリゴヌクレオチドを化学開裂および脱保護するための組成物および方法 |
| EP3870593A4 (en) | 2018-10-25 | 2022-11-16 | Singular Genomics Systems, Inc. | NUCLEOTIDE ANALOGUES |
| AU2018448937B2 (en) | 2018-11-07 | 2024-08-15 | Qingdao MGI Tech Co., Ltd. | Method for sequencing polynucleotides |
| KR20210098844A (ko) | 2018-12-05 | 2021-08-11 | 일루미나, 인코포레이티드 | 중합효소, 조성물, 및 사용 방법 |
| JP7296409B2 (ja) * | 2018-12-17 | 2023-06-22 | イルミナ ケンブリッジ リミテッド | ポリヌクレオチドシーケンシングに使用するための組成物 |
| US11440933B2 (en) * | 2018-12-19 | 2022-09-13 | Roche Sequencing Solutions, Inc. | 3′ protected nucleotides |
| US11293061B2 (en) * | 2018-12-26 | 2022-04-05 | Illumina Cambridge Limited | Sequencing methods using nucleotides with 3′ AOM blocking group |
| JP2022516684A (ja) | 2019-01-08 | 2022-03-01 | シンギュラー・ゲノミクス・システムズ・インコーポレイテッド | ヌクレオチドの開裂可能なリンカーおよびその使用 |
| KR102829192B1 (ko) | 2019-03-01 | 2025-07-04 | 일루미나 케임브리지 리미티드 | 엑소사이클릭 아민 치환된 쿠마린 화합물 및 형광 표지로서의 이의 용도 |
| EP3931190A1 (en) | 2019-03-01 | 2022-01-05 | Illumina Cambridge Limited | Tertiary amine substituted coumarin compounds and their uses as fluorescent labels |
| NL2023327B1 (en) | 2019-03-01 | 2020-09-17 | Illumina Inc | Multiplexed fluorescent detection of analytes |
| WO2020178231A1 (en) | 2019-03-01 | 2020-09-10 | Illumina, Inc. | Multiplexed fluorescent detection of analytes |
| US11421271B2 (en) | 2019-03-28 | 2022-08-23 | Illumina Cambridge Limited | Methods and compositions for nucleic acid sequencing using photoswitchable labels |
| AU2019445584B2 (en) | 2019-05-15 | 2024-09-05 | Qingdao MGI Tech Co., Ltd. | Single-channel sequencing method based on self-luminescence |
| US20230242979A1 (en) * | 2019-08-20 | 2023-08-03 | Egi Tech (Shen Zhen) Co., Limited | Method for sequencing polynucleotides based on optical signal kinetics of luminescent labels and secondary luminescent signals |
| AU2020389779A1 (en) | 2019-11-27 | 2022-05-26 | Illumina Cambridge Limited | Cyclooctatetraene containing dyes and compositions |
| US11174281B1 (en) | 2020-04-24 | 2021-11-16 | Singular Genomics Systems, Inc. | Modified nucleotides and uses thereof |
| CN115867560B (zh) | 2020-06-22 | 2025-03-28 | 伊鲁米纳剑桥有限公司 | 具有3’缩醛封端基团的核苷与核苷酸 |
| JP2023533745A (ja) * | 2020-07-07 | 2023-08-04 | サイクラリティ・セラピューティクス・インコーポレイテッド | シクロデキストリン二量体及びその使用 |
| US11981964B2 (en) | 2020-07-28 | 2024-05-14 | Illumina Cambridge Limited | Substituted coumarin dyes and uses as fluorescent labels |
| WO2022083686A1 (zh) * | 2020-10-21 | 2022-04-28 | 深圳华大生命科学研究院 | 修饰的核苷或核苷酸 |
| US20220195517A1 (en) | 2020-12-17 | 2022-06-23 | Illumina Cambridge Limited | Long stokes shift chromenoquinoline dyes and uses in sequencing applications |
| US20220195516A1 (en) | 2020-12-17 | 2022-06-23 | Illumina Cambridge Limited | Methods, systems and compositions for nucleic acid sequencing |
| US20220195196A1 (en) | 2020-12-17 | 2022-06-23 | Illumina Cambridge Limited | Alkylpyridinium coumarin dyes and uses in sequencing applications |
| US20220195518A1 (en) | 2020-12-22 | 2022-06-23 | Illumina Cambridge Limited | Methods and compositions for nucleic acid sequencing |
| JP2024516191A (ja) | 2021-05-05 | 2024-04-12 | イルミナ ケンブリッジ リミテッド | ビス－ホウ素縮合複素環を含有する蛍光色素及び配列決定における使用 |
| EP4347857A1 (en) * | 2021-05-26 | 2024-04-10 | Illumina, Inc. | Purifying and polymerizing 3'-blocked nucleotides |
| EP4359555A1 (en) | 2021-06-23 | 2024-05-01 | Illumina, Inc. | Compositions, methods, kits, cartridges, and systems for sequencing reagents |
| US12435369B2 (en) | 2021-08-13 | 2025-10-07 | Singular Genomcis Systems, Inc. | Nucleotide analogs and uses thereof |
| US12077789B2 (en) | 2021-08-14 | 2024-09-03 | Illumina, Inc. | Polymerases, compositions, and methods of use |
| CN115943217A (zh) | 2021-09-07 | 2023-04-07 | 深圳华大智造科技股份有限公司 | 一种用于分析靶多核苷酸的序列的方法 |
| AU2021463802A1 (en) | 2021-09-07 | 2024-03-28 | Mgi Tech Co., Ltd. | Method for analyzing sequence of target polynucleotide |
| WO2023107673A2 (en) | 2021-12-10 | 2023-06-15 | Singular Genomics Systems, Inc. | Cleavable disulfide linkers and uses thereof |
| JP2023130947A (ja) * | 2022-03-08 | 2023-09-21 | 国立大学法人東海国立大学機構 | ビスホスホリル架橋スチルベン化合物及び油滴染色剤 |
| EP4499862A1 (en) | 2022-03-28 | 2025-02-05 | Illumina, Inc. | Labeled avidin and methods for sequencing |
| WO2023186819A1 (en) | 2022-03-29 | 2023-10-05 | Illumina Cambridge Limited | Chromenoquinoline dyes and uses in sequencing |
| WO2023192900A1 (en) | 2022-03-31 | 2023-10-05 | Illumina Singapore Pte. Ltd. | Nucleosides and nucleotides with 3' vinyl blocking group useful in sequencing by synthesis |
| AU2023246851A1 (en) | 2022-03-31 | 2024-01-18 | Illumina, Inc. | Compositions and methods for improving sequencing signals |
| CN119301275A (zh) | 2022-05-31 | 2025-01-10 | 伊路米纳有限公司 | 用于核酸测序的组合物和方法 |
| WO2024003087A1 (en) | 2022-06-28 | 2024-01-04 | Illumina, Inc. | Fluorescent dyes containing fused tetracyclic bis-boron heterocycle and uses in sequencing |
| CA3246518A1 (en) | 2022-09-30 | 2024-04-04 | Illumina, Inc. | Compositions and methods for reducing photolesions during sequencing |
| WO2024123866A1 (en) | 2022-12-09 | 2024-06-13 | Illumina, Inc. | Nucleosides and nucleotides with 3´ blocking groups and cleavable linkers |
| CA3246559A1 (en) | 2022-12-27 | 2024-07-04 | Illumina, Inc. | SEQUENCE PROCESSES USING ALLYL 3' BLOCKED NUCLEOTIDES |
| CN119452044A (zh) | 2023-03-29 | 2025-02-14 | 因美纳公司 | 萘酰亚胺染料以及其在核酸测序中的用途 |
| CN119061122A (zh) | 2023-05-30 | 2024-12-03 | 深圳市真迈生物科技有限公司 | 单分子测序方法 |
| US20250075269A1 (en) | 2023-08-31 | 2025-03-06 | Illumina, Inc. | Compositions and methods for nucleic acid sequencing |
| WO2025090596A1 (en) | 2023-10-26 | 2025-05-01 | Illumina, Inc. | 4,5-substituted naphthalimide dyes and uses in nucleic acid sequencing |
| WO2025106715A1 (en) | 2023-11-17 | 2025-05-22 | Illumina, Inc. | Conjugated polymers or polymer dots as fluorescent labels |
| US20250197933A1 (en) | 2023-12-18 | 2025-06-19 | Illumina, Inc. | Hydrogel nanoparticles as labeling scaffold in sequencing |
| CN117867664B (zh) * | 2023-12-25 | 2024-11-26 | 康龙化成(宁波)科技发展有限公司 | 一种On-DNA亚磺酰亚胺类化合物及其合成方法 |
| US20250215493A1 (en) | 2023-12-28 | 2025-07-03 | Illumina, Inc. | Nucleotides with enzymatically cleavable 3'-o-glycoside blocking groups for sequencing |
| WO2025144711A1 (en) | 2023-12-29 | 2025-07-03 | Illumina, Inc. | Tricyclic polymethine dyes for nucleic acid sequencing |
| CN117886850B (zh) * | 2024-03-14 | 2024-07-05 | 深圳赛陆医疗科技有限公司 | 一种叠氮化合物的制备方法 |
| WO2025221895A1 (en) | 2024-04-19 | 2025-10-23 | Illumina, Inc. | Water soluble polymer scaffolds for dye labeling |
| WO2025230914A1 (en) | 2024-04-29 | 2025-11-06 | Illumina, Inc. | Nucleotides with enzyme-triggered self-immolative linkers for sequencing by synthesis |
Family Cites Families (178)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4711955A (en) | 1981-04-17 | 1987-12-08 | Yale University | Modified nucleotides and methods of preparing and using same |
| US5175269A (en) | 1984-01-30 | 1992-12-29 | Enzo Diagnostics, Inc. | Compound and detectable molecules having an oligo- or polynucleotide with modifiable reactive group |
| US5118605A (en) | 1984-10-16 | 1992-06-02 | Chiron Corporation | Polynucleotide determination with selectable cleavage sites |
| US4824775A (en) | 1985-01-03 | 1989-04-25 | Molecular Diagnostics, Inc. | Cells labeled with multiple Fluorophores bound to a nucleic acid carrier |
| US4772691A (en) | 1985-06-05 | 1988-09-20 | The Medical College Of Wisconsin, Inc. | Chemically cleavable nucleotides |
| US4863849A (en) | 1985-07-18 | 1989-09-05 | New York Medical College | Automatable process for sequencing nucleotide |
| US4888274A (en) | 1985-09-18 | 1989-12-19 | Yale University | RecA nucleoprotein filament and methods |
| US5242796A (en) | 1986-07-02 | 1993-09-07 | E. I. Du Pont De Nemours And Company | Method, system and reagents for DNA sequencing |
| US5047519A (en) | 1986-07-02 | 1991-09-10 | E. I. Du Pont De Nemours And Company | Alkynylamino-nucleotides |
| US5151507A (en) | 1986-07-02 | 1992-09-29 | E. I. Du Pont De Nemours And Company | Alkynylamino-nucleotides |
| US4900686A (en) | 1987-04-02 | 1990-02-13 | Polaroid Corporation | Fluorescent conjugates and biological diagnostic assay |
| GB8810400D0 (en) | 1988-05-03 | 1988-06-08 | Southern E | Analysing polynucleotide sequences |
| SE8801070D0 (sv) | 1988-03-23 | 1988-03-23 | Pharmacia Ab | Method for immobilizing a dna sequence on a solid support |
| US4971903A (en) | 1988-03-25 | 1990-11-20 | Edward Hyman | Pyrophosphate-based method and apparatus for sequencing nucleic acids |
| US5174962A (en) | 1988-06-20 | 1992-12-29 | Genomyx, Inc. | Apparatus for determining DNA sequences by mass spectrometry |
| GB8822228D0 (en) | 1988-09-21 | 1988-10-26 | Southern E M | Support-bound oligonucleotides |
| GB8910880D0 (en) | 1989-05-11 | 1989-06-28 | Amersham Int Plc | Sequencing method |
| US5800992A (en) | 1989-06-07 | 1998-09-01 | Fodor; Stephen P.A. | Method of detecting nucleic acids |
| US5547839A (en) | 1989-06-07 | 1996-08-20 | Affymax Technologies N.V. | Sequencing of surface immobilized polymers utilizing microflourescence detection |
| US6346413B1 (en) | 1989-06-07 | 2002-02-12 | Affymetrix, Inc. | Polymer arrays |
| DE3924454A1 (de) | 1989-07-24 | 1991-02-07 | Cornelis P Prof Dr Hollenberg | Die anwendung von dna und dna-technologie fuer die konstruktion von netzwerken zur verwendung in der chip-konstruktion und chip-produktion (dna chips) |
| US5302509A (en) | 1989-08-14 | 1994-04-12 | Beckman Instruments, Inc. | Method for sequencing polynucleotides |
| WO1991006678A1 (en) | 1989-10-26 | 1991-05-16 | Sri International | Dna sequencing |
| AU2674092A (en) | 1991-09-09 | 1993-04-05 | Baylor College Of Medicine | Method and device for rapid dna or rna sequencing determination by a base addition sequencing scheme |
| ES2097925T3 (es) | 1991-09-18 | 1997-04-16 | Affymax Tech Nv | Metodo para sintetizar diversas colecciones de oligomeros. |
| WO1993009668A1 (en) | 1991-11-22 | 1993-05-27 | Affymax Technology N.V. | Combinatorial strategies for polymer synthesis |
| DE4141178A1 (de) | 1991-12-13 | 1993-06-17 | Europ Lab Molekularbiolog | Verfahren zur sequenzierung von nukleinsaeuren |
| DE69333650T2 (de) | 1992-02-19 | 2006-01-12 | The Public Health Research Institute Of The City Of New York, Inc. | Neue anordnungn von oligonukleotiden und ihr nutzen zum sortieren, isolieren, sequenzieren und manipulieren von nukleinsäuren |
| GB9208733D0 (en) | 1992-04-22 | 1992-06-10 | Medical Res Council | Dna sequencing method |
| GB9210176D0 (en) | 1992-05-12 | 1992-06-24 | Cemu Bioteknik Ab | Chemical method |
| US5583211A (en) | 1992-10-29 | 1996-12-10 | Beckman Instruments, Inc. | Surface activated organic polymers useful for location - specific attachment of nucleic acids, peptides, proteins and oligosaccharides |
| US5516664A (en) | 1992-12-23 | 1996-05-14 | Hyman; Edward D. | Enzymatic synthesis of repeat regions of oligonucleotides |
| US5436143A (en) | 1992-12-23 | 1995-07-25 | Hyman; Edward D. | Method for enzymatic synthesis of oligonucleotides |
| US6074823A (en) | 1993-03-19 | 2000-06-13 | Sequenom, Inc. | DNA sequencing by mass spectrometry via exonuclease degradation |
| FR2703052B1 (fr) | 1993-03-26 | 1995-06-02 | Pasteur Institut | Nouvelle méthode de séquençage d'acides nucléiques. |
| US5959089A (en) | 1993-07-19 | 1999-09-28 | Hannessian; Stephen | Amino-cyclodextrin syntheses |
| GB9315847D0 (en) | 1993-07-30 | 1993-09-15 | Isis Innovation | Tag reagent and assay method |
| US5547859A (en) | 1993-08-02 | 1996-08-20 | Goodman; Myron F. | Chain-terminating nucleotides for DNA sequencing methods |
| US5472672A (en) | 1993-10-22 | 1995-12-05 | The Board Of Trustees Of The Leland Stanford Junior University | Apparatus and method for polymer synthesis using arrays |
| US6156501A (en) | 1993-10-26 | 2000-12-05 | Affymetrix, Inc. | Arrays of modified nucleic acid probes and methods of use |
| JPH09507121A (ja) | 1993-10-26 | 1997-07-22 | アフィマックス テクノロジーズ ナームロゼ ベノートスハップ | 生物学的チップ上の核酸プローブアレー |
| US5429807A (en) | 1993-10-28 | 1995-07-04 | Beckman Instruments, Inc. | Method and apparatus for creating biopolymer arrays on a solid support surface |
| WO1995014108A1 (en) | 1993-11-17 | 1995-05-26 | Amersham International Plc | Primer extension mass spectroscopy nucleic acid sequencing method |
| US5552278A (en) | 1994-04-04 | 1996-09-03 | Spectragen, Inc. | DNA sequencing by stepwise ligation and cleavage |
| US5807522A (en) | 1994-06-17 | 1998-09-15 | The Board Of Trustees Of The Leland Stanford Junior University | Methods for fabricating microarrays of biological samples |
| US6232465B1 (en) | 1994-09-02 | 2001-05-15 | Andrew C. Hiatt | Compositions for enzyme catalyzed template-independent creation of phosphodiester bonds using protected nucleotides |
| US6214987B1 (en) | 1994-09-02 | 2001-04-10 | Andrew C. Hiatt | Compositions for enzyme catalyzed template-independent formation of phosphodiester bonds using protected nucleotides |
| US5808045A (en) | 1994-09-02 | 1998-09-15 | Andrew C. Hiatt | Compositions for enzyme catalyzed template-independent creation of phosphodiester bonds using protected nucleotides |
| US5763594A (en) | 1994-09-02 | 1998-06-09 | Andrew C. Hiatt | 3' protected nucleotides for enzyme catalyzed template-independent creation of phosphodiester bonds |
| US5872244A (en) | 1994-09-02 | 1999-02-16 | Andrew C. Hiatt | 3' protected nucleotides for enzyme catalyzed template-independent creation of phosphodiester bonds |
| US6013445A (en) | 1996-06-06 | 2000-01-11 | Lynx Therapeutics, Inc. | Massively parallel signature sequencing by ligation of encoded adaptors |
| US5604097A (en) | 1994-10-13 | 1997-02-18 | Spectragen, Inc. | Methods for sorting polynucleotides using oligonucleotide tags |
| CA2202480A1 (en) | 1994-10-14 | 1996-04-25 | Jane Charlotte Moores | Porphyrin labeling of polynucleotides |
| US5556752A (en) | 1994-10-24 | 1996-09-17 | Affymetrix, Inc. | Surface-bound, unimolecular, double-stranded DNA |
| US5681940A (en) | 1994-11-02 | 1997-10-28 | Icn Pharmaceuticals | Sugar modified nucleosides and oligonucleotides |
| DE4438918A1 (de) | 1994-11-04 | 1996-05-09 | Hoechst Ag | Modifizierte Oligonukleotide, deren Herstellung sowie deren Verwendung |
| SE9500342D0 (sv) | 1995-01-31 | 1995-01-31 | Marek Kwiatkowski | Novel chain terminators, the use thereof for nucleic acid sequencing and synthesis and a method of their preparation |
| AU5171696A (en) | 1995-02-27 | 1996-09-18 | Ely Michael Rabani | Device, compounds, algorithms, and methods of molecular characterization and manipulation with molecular parallelism |
| US5750341A (en) | 1995-04-17 | 1998-05-12 | Lynx Therapeutics, Inc. | DNA sequencing by parallel oligonucleotide extensions |
| US5624711A (en) | 1995-04-27 | 1997-04-29 | Affymax Technologies, N.V. | Derivatization of solid supports and methods for oligomer synthesis |
| EP0745686A1 (en) | 1995-06-01 | 1996-12-04 | Roche Diagnostics GmbH | The use of DNA polymerase 3'-intrinsic editing activity |
| US5545531A (en) | 1995-06-07 | 1996-08-13 | Affymax Technologies N.V. | Methods for making a device for concurrently processing multiple biological chip assays |
| US5728528A (en) | 1995-09-20 | 1998-03-17 | The Regents Of The University Of California | Universal spacer/energy transfer dyes |
| DE69638321D1 (de) | 1995-10-11 | 2011-03-03 | Luminex Corp | Gleichzeitige mehrfachanalyse klinischer proben |
| US5658734A (en) | 1995-10-17 | 1997-08-19 | International Business Machines Corporation | Process for synthesizing chemical compounds |
| US6613508B1 (en) | 1996-01-23 | 2003-09-02 | Qiagen Genomics, Inc. | Methods and compositions for analyzing nucleic acid molecules utilizing sizing techniques |
| US6312893B1 (en) | 1996-01-23 | 2001-11-06 | Qiagen Genomics, Inc. | Methods and compositions for determining the sequence of nucleic acid molecules |
| EP0992511B1 (en) | 1996-01-23 | 2009-03-11 | Operon Biotechnologies, Inc. | Methods and compositions for determining the sequence of nucleic acid molecules |
| US6458530B1 (en) | 1996-04-04 | 2002-10-01 | Affymetrix Inc. | Selecting tag nucleic acids |
| US6005125A (en) | 1996-05-06 | 1999-12-21 | Rutgers The State University Of New Jersey | Universal allyl linker for solid-phase nucleic acid synthesis |
| US5821356A (en) | 1996-08-12 | 1998-10-13 | The Perkin Elmer Corporation | Propargylethoxyamino nucleotides |
| US5921971A (en) | 1996-09-13 | 1999-07-13 | Boston Scientific Corporation | Single operator exchange biliary catheter |
| GB9620209D0 (en) | 1996-09-27 | 1996-11-13 | Cemu Bioteknik Ab | Method of sequencing DNA |
| US5885775A (en) | 1996-10-04 | 1999-03-23 | Perseptive Biosystems, Inc. | Methods for determining sequences information in polynucleotides using mass spectrometry |
| GB9626815D0 (en) | 1996-12-23 | 1997-02-12 | Cemu Bioteknik Ab | Method of sequencing DNA |
| CA2277545A1 (en) | 1997-01-08 | 1998-07-16 | Proligo Llc | Bioconjugation of oligonucleotides |
| US6046005A (en) | 1997-01-15 | 2000-04-04 | Incyte Pharmaceuticals, Inc. | Nucleic acid sequencing with solid phase capturable terminators comprising a cleavable linking group |
| US6297006B1 (en) | 1997-01-16 | 2001-10-02 | Hyseq, Inc. | Methods for sequencing repetitive sequences and for determining the order of sequence subfragments |
| US6136543A (en) | 1997-01-31 | 2000-10-24 | Hitachi, Ltd. | Method for determining nucleic acids base sequence and apparatus therefor |
| ATE273381T1 (de) | 1997-02-12 | 2004-08-15 | Eugene Y Chan | Verfahren zur analyse von polymeren |
| US6544797B1 (en) | 1997-04-09 | 2003-04-08 | Biosite Diagnostics, Inc. | Compositions and methods for inhibiting light-induced inactivation of biological reagents |
| JP3489991B2 (ja) | 1997-07-07 | 2004-01-26 | 理化学研究所 | ３’−デオキシリボヌクレオチド誘導体 |
| IL133411A (en) | 1997-07-28 | 2003-09-17 | Medical Biosystems Ltd | Nucleic acid sequence analysis |
| US6008379A (en) | 1997-10-01 | 1999-12-28 | The Perkin-Elmer Corporation | Aromatic-substituted xanthene dyes |
| US6511803B1 (en) | 1997-10-10 | 2003-01-28 | President And Fellows Of Harvard College | Replica amplification of nucleic acid arrays |
| US6485944B1 (en) | 1997-10-10 | 2002-11-26 | President And Fellows Of Harvard College | Replica amplification of nucleic acid arrays |
| JP2001519538A (ja) | 1997-10-10 | 2001-10-23 | プレジデント・アンド・フェローズ・オブ・ハーバード・カレッジ | 核酸アレイのレプリカ増幅 |
| GB9815163D0 (en) | 1998-07-13 | 1998-09-09 | Brax Genomics Ltd | Compounds |
| US6087102A (en) | 1998-01-07 | 2000-07-11 | Clontech Laboratories, Inc. | Polymeric arrays and methods for their use in binding assays |
| US6287776B1 (en) | 1998-02-02 | 2001-09-11 | Signature Bioscience, Inc. | Method for detecting and classifying nucleic acid hybridization |
| JP3944996B2 (ja) | 1998-03-05 | 2007-07-18 | 株式会社日立製作所 | Ｄｎａプローブアレー |
| WO1999049082A2 (en) | 1998-03-23 | 1999-09-30 | Invitrogen Corporation | Modified nucleotides and methods useful for nucleic acid sequencing |
| US6780591B2 (en) | 1998-05-01 | 2004-08-24 | Arizona Board Of Regents | Method of determining the nucleotide sequence of oligonucleotides and DNA molecules |
| JP3813818B2 (ja) | 1998-05-01 | 2006-08-23 | アリゾナ ボード オブ リージェンツ | オリゴヌクレオチドおよびｄｎａ分子のヌクレオチド配列の決定方法 |
| US6096875A (en) | 1998-05-29 | 2000-08-01 | The Perlein-Elmer Corporation | Nucleotide compounds including a rigid linker |
| US6218530B1 (en) | 1998-06-02 | 2001-04-17 | Ambergen Inc. | Compounds and methods for detecting biomolecules |
| US6287821B1 (en) | 1998-06-11 | 2001-09-11 | Orchid Biosciences, Inc. | Nucleotide analogues with 3'-pro-fluorescent fluorophores in nucleic acid sequence analysis |
| US6031078A (en) | 1998-06-16 | 2000-02-29 | Millennium Pharmaceuticals, Inc. | MTbx protein and nucleic acid molecules and uses therefor |
| US6335155B1 (en) | 1998-06-26 | 2002-01-01 | Sunesis Pharmaceuticals, Inc. | Methods for rapidly identifying small organic molecule ligands for binding to biological target molecules |
| US6218118B1 (en) | 1998-07-09 | 2001-04-17 | Agilent Technologies, Inc. | Method and mixture reagents for analyzing the nucleotide sequence of nucleic acids by mass spectrometry |
| DE69928265T3 (de) | 1998-07-30 | 2013-11-28 | Illumina Cambridge Ltd. | Matrizen von biomolekülen und ihre verwendung in sequenzierung |
| GB0002310D0 (en) | 2000-02-01 | 2000-03-22 | Solexa Ltd | Polynucleotide sequencing |
| US6787308B2 (en) | 1998-07-30 | 2004-09-07 | Solexa Ltd. | Arrayed biomolecules and their use in sequencing |
| DE19844931C1 (de) | 1998-09-30 | 2000-06-15 | Stefan Seeger | Verfahren zur DNS- oder RNS-Sequenzierung |
| US6277628B1 (en) | 1998-10-02 | 2001-08-21 | Incyte Genomics, Inc. | Linear microarrays |
| US6221592B1 (en) | 1998-10-20 | 2001-04-24 | Wisconsin Alumi Research Foundation | Computer-based methods and systems for sequencing of individual nucleic acid molecules |
| US6451525B1 (en) | 1998-12-03 | 2002-09-17 | Pe Corporation (Ny) | Parallel sequencing method |
| US6232075B1 (en) | 1998-12-14 | 2001-05-15 | Li-Cor, Inc. | Heterogeneous assay for pyrophosphate detection |
| US6380378B1 (en) | 1998-12-24 | 2002-04-30 | Toagosei Company, Ltd. | Nucleotide compound, nucleotide block oligonucleotide, and method for producing them |
| US6087112A (en) | 1998-12-30 | 2000-07-11 | Oligos Etc. Inc. | Arrays with modified oligonucleotide and polynucleotide compositions |
| EP2177627B1 (en) | 1999-02-23 | 2012-05-02 | Caliper Life Sciences, Inc. | Manipulation of microparticles in microfluidic systems |
| AU3174600A (en) | 1999-03-10 | 2000-09-28 | Asm Scientific, Inc. | A method for direct nucleic acid sequencing |
| ATE413467T1 (de) | 1999-04-20 | 2008-11-15 | Illumina Inc | Detektion von nukleinsäurereaktionen auf kügelchen-arrays |
| US6355431B1 (en) | 1999-04-20 | 2002-03-12 | Illumina, Inc. | Detection of nucleic acid amplification reactions using bead arrays |
| US20050191698A1 (en) | 1999-04-20 | 2005-09-01 | Illumina, Inc. | Nucleic acid sequencing using microsphere arrays |
| US7037654B2 (en) | 1999-04-30 | 2006-05-02 | Aclara Biosciences, Inc. | Methods and compositions for enhancing detection in determinations employing cleavable electrophoretic tag reagents |
| US7056661B2 (en) | 1999-05-19 | 2006-06-06 | Cornell Research Foundation, Inc. | Method for sequencing nucleic acid molecules |
| US6750357B1 (en) | 1999-06-25 | 2004-06-15 | Syngen, Inc. | Rhodamine-based fluorophores useful as labeling reagents |
| US6818395B1 (en) | 1999-06-28 | 2004-11-16 | California Institute Of Technology | Methods and apparatus for analyzing polynucleotide sequences |
| US6242193B1 (en) | 1999-07-30 | 2001-06-05 | Hitachi, Ltd. | Apparatus for determining base sequence of nucleic acid |
| US6982146B1 (en) | 1999-08-30 | 2006-01-03 | The United States Of America As Represented By The Department Of Health And Human Services | High speed parallel molecular nucleic acid sequencing |
| WO2001016375A2 (en) | 1999-08-30 | 2001-03-08 | The Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | High speed parallel molecular nucleic acid sequencing |
| US7244559B2 (en) | 1999-09-16 | 2007-07-17 | 454 Life Sciences Corporation | Method of sequencing a nucleic acid |
| US6274320B1 (en) | 1999-09-16 | 2001-08-14 | Curagen Corporation | Method of sequencing a nucleic acid |
| EP1218543A2 (en) | 1999-09-29 | 2002-07-03 | Solexa Ltd. | Polynucleotide sequencing |
| US6309836B1 (en) * | 1999-10-05 | 2001-10-30 | Marek Kwiatkowski | Compounds for protecting hydroxyls and methods for their use |
| WO2001032930A1 (en) | 1999-11-04 | 2001-05-10 | California Institute Of Technology | Methods and apparatuses for analyzing polynucleotide sequences |
| WO2001048184A2 (de) | 1999-12-23 | 2001-07-05 | Axaron Bioscience Ag | Verfahren zur parallelen sequenzierung eines nukleinsäuregemisches an einer oberfläche |
| GB0002389D0 (en) | 2000-02-02 | 2000-03-22 | Solexa Ltd | Molecular arrays |
| US6770441B2 (en) | 2000-02-10 | 2004-08-03 | Illumina, Inc. | Array compositions and methods of making same |
| MXPA02008078A (es) | 2000-02-18 | 2002-11-29 | Julio Javier Cristiani | Metodo para el tratamiento o prevencion de infecciones por flavivirus utilizando analogos de nucleosidos. |
| JP4721606B2 (ja) | 2000-03-30 | 2011-07-13 | トヨタ自動車株式会社 | 単一核酸分子の塩基配列決定法 |
| GB0013276D0 (en) | 2000-06-01 | 2000-07-26 | Amersham Pharm Biotech Uk Ltd | Nucleotide analogues |
| GB0016473D0 (en) | 2000-07-05 | 2000-08-23 | Amersham Pharm Biotech Uk Ltd | Sequencing method |
| AU8288101A (en) | 2000-07-07 | 2002-01-21 | Visigen Biotechnologies Inc | Real-time sequence determination |
| DE10041539A1 (de) | 2000-08-24 | 2002-03-07 | Febit Ferrarius Biotech Gmbh | Neue Amiditderivate zur Synthese von Polymeren auf Oberflächen |
| WO2002022883A1 (en) | 2000-09-11 | 2002-03-21 | The Trustees Of Columbia University In The City Of New York | Combinatorial fluorescence energy transfer tags and uses thereof |
| WO2002029003A2 (en) | 2000-10-06 | 2002-04-11 | The Trustees Of Columbia University In The City Of New York | Massive parallel method for decoding dna and rna |
| US20020155476A1 (en) | 2000-10-20 | 2002-10-24 | Nader Pourmand | Transient electrical signal based methods and devices for characterizing molecular interaction and/or motion in a sample |
| US7211414B2 (en) | 2000-12-01 | 2007-05-01 | Visigen Biotechnologies, Inc. | Enzymatic nucleic acid synthesis: compositions and methods for altering monomer incorporation fidelity |
| JP2004523243A (ja) | 2001-03-12 | 2004-08-05 | カリフォルニア インスティチュート オブ テクノロジー | 非同期性塩基伸長によってポリヌクレオチド配列を分析するための方法および装置 |
| US20030027140A1 (en) | 2001-03-30 | 2003-02-06 | Jingyue Ju | High-fidelity DNA sequencing using solid phase capturable dideoxynucleotides and mass spectrometry |
| DE10120797B4 (de) | 2001-04-27 | 2005-12-22 | Genovoxx Gmbh | Verfahren zur Analyse von Nukleinsäureketten |
| DE10120798B4 (de) | 2001-04-27 | 2005-12-29 | Genovoxx Gmbh | Verfahren zur Bestimmung der Genexpression |
| US6613523B2 (en) | 2001-06-29 | 2003-09-02 | Agilent Technologies, Inc. | Method of DNA sequencing using cleavable tags |
| CA2452474C (en) | 2001-07-13 | 2012-03-06 | Ambergen, Inc. | Nucleotide compositions comprising photocleavable markers and methods of preparation thereof |
| AU2002337030A1 (en) | 2001-08-29 | 2003-03-18 | Genovoxx Gmbh | Method for analyzing nucleic acid sequences and gene expression |
| GB0128526D0 (en) | 2001-11-29 | 2002-01-23 | Amersham Pharm Biotech Uk Ltd | Nucleotide analogues |
| GB0129012D0 (en) | 2001-12-04 | 2002-01-23 | Solexa Ltd | Labelled nucleotides |
| US7057026B2 (en) * | 2001-12-04 | 2006-06-06 | Solexa Limited | Labelled nucleotides |
| US20030180769A1 (en) | 2002-02-05 | 2003-09-25 | Metzker Michael L. | Substituted 4,4-difluoro-4-bora-3A,4A-diaza-s-indacene compounds for 8-color DNA sequencing |
| JP4230364B2 (ja) | 2002-04-04 | 2009-02-25 | バイオタージ アクチボラゲット | 新しい方法 |
| US20040014096A1 (en) | 2002-04-12 | 2004-01-22 | Stratagene | Dual-labeled nucleotides |
| US7074597B2 (en) | 2002-07-12 | 2006-07-11 | The Trustees Of Columbia University In The City Of New York | Multiplex genotyping using solid phase capturable dideoxynucleotides and mass spectrometry |
| EP3438116B1 (en) | 2002-08-23 | 2021-02-17 | Illumina Cambridge Limited | Labelled nucleotides |
| US7414116B2 (en) | 2002-08-23 | 2008-08-19 | Illumina Cambridge Limited | Labelled nucleotides |
| ES2550513T3 (es) | 2002-08-23 | 2015-11-10 | Illumina Cambridge Limited | Nucleótidos modificados para secuenciación de polinucleótidos |
| US7595883B1 (en) | 2002-09-16 | 2009-09-29 | The Board Of Trustees Of The Leland Stanford Junior University | Biological analysis arrangement and approach therefor |
| GB0321306D0 (en) | 2003-09-11 | 2003-10-15 | Solexa Ltd | Modified polymerases for improved incorporation of nucleotide analogues |
| EP2436778A3 (en) | 2004-03-03 | 2012-07-11 | The Trustees of Columbia University in the City of New York | Photocleavable fluorescent nucleotides for DNA sequencing on chip constructed by site-specific coupling chemistry |
| WO2006044078A2 (en) | 2004-09-17 | 2006-04-27 | Pacific Biosciences Of California, Inc. | Apparatus and method for analysis of molecules |
| US7393533B1 (en) | 2004-11-08 | 2008-07-01 | La Jolla Institute For Allergy And Immunology | H3L envelope protein immunization methods and H3L envelope passive protection methods |
| GB0517097D0 (en) | 2005-08-19 | 2005-09-28 | Solexa Ltd | Modified nucleosides and nucleotides and uses thereof |
| US7405281B2 (en) | 2005-09-29 | 2008-07-29 | Pacific Biosciences Of California, Inc. | Fluorescent nucleotide analogs and uses therefor |
| EP4105644A3 (en) | 2006-03-31 | 2022-12-28 | Illumina, Inc. | Systems and devices for sequence by synthesis analysis |
| WO2008051530A2 (en) | 2006-10-23 | 2008-05-02 | Pacific Biosciences Of California, Inc. | Polymerase enzymes and reagents for enhanced nucleic acid sequencing |
| US8349167B2 (en) | 2006-12-14 | 2013-01-08 | Life Technologies Corporation | Methods and apparatus for detecting molecular interactions using FET arrays |
| US8262900B2 (en) | 2006-12-14 | 2012-09-11 | Life Technologies Corporation | Methods and apparatus for measuring analytes using large scale FET arrays |
| AU2007334393A1 (en) | 2006-12-14 | 2008-06-26 | Life Technologies Corporation | Methods and apparatus for measuring analytes using large scale FET arrays |
| US8481259B2 (en) | 2007-02-05 | 2013-07-09 | Intelligent Bio-Systems, Inc. | Methods and devices for sequencing nucleic acids in smaller batches |
| EP3431615A3 (en) * | 2007-10-19 | 2019-02-20 | The Trustees of Columbia University in the City of New York | Dna sequencing with non-fluorescent nucleotide reversible terminators cleavable label modified nucleotide terminators |
| US20100035253A1 (en) | 2008-03-19 | 2010-02-11 | Intelligent Bio-Systems, Inc. | Methods And Compositions For Incorporating Nucleotides |
| US20100137143A1 (en) | 2008-10-22 | 2010-06-03 | Ion Torrent Systems Incorporated | Methods and apparatus for measuring analytes |
| US9309569B2 (en) | 2010-08-26 | 2016-04-12 | Intelligent Bio-Systems, Inc. | Methods and compositions for sequencing nucleic acid using charge |
| WO2012083249A2 (en) * | 2010-12-17 | 2012-06-21 | The Trustees Of Columbia University In The City Of New York | Dna sequencing by synthesis using modified nucleotides and nanopore detection |
| WO2012162429A2 (en) * | 2011-05-23 | 2012-11-29 | The Trustees Of Columbia University In The City Of New York | Dna sequencing by synthesis using raman and infrared spectroscopy detection |
| WO2013044018A1 (en) | 2011-09-23 | 2013-03-28 | Illumina, Inc. | Methods and compositions for nucleic acid sequencing |
| KR102230831B1 (ko) | 2013-03-15 | 2021-03-22 | 일루미나 케임브리지 리미티드 | 변형된 뉴클레오사이드 또는 뉴클레오타이드 |
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| CN105377869A (zh) | 2016-03-02 |
| US20200087725A1 (en) | 2020-03-19 |
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| CA2903095A1 (en) | 2014-09-18 |
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| AU2013382358A1 (en) | 2015-09-17 |
| CN105377869B (zh) | 2018-07-10 |
| KR101874680B1 (ko) | 2018-07-04 |
| BR112015022448A2 (pt) | 2017-07-18 |
| US10982277B2 (en) | 2021-04-20 |
| KR20180077296A (ko) | 2018-07-06 |
| US9593373B2 (en) | 2017-03-14 |
| US20160002721A1 (en) | 2016-01-07 |
| CN108864232B (zh) | 2022-01-04 |
| CN108864232A (zh) | 2018-11-23 |
| EP2970356A1 (en) | 2016-01-20 |
| ES2685549T3 (es) | 2018-10-09 |
| JP2016512206A (ja) | 2016-04-25 |
| EP2970356B1 (en) | 2018-05-30 |
| AU2013382358B2 (en) | 2017-01-12 |
| DK2970356T3 (en) | 2018-08-27 |
| US20170166961A1 (en) | 2017-06-15 |
| KR102230831B1 (ko) | 2021-03-22 |
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