WO2008037568A3 - Reversible terminators for efficient sequencing by synthesis - Google Patents
Reversible terminators for efficient sequencing by synthesis Download PDFInfo
- Publication number
- WO2008037568A3 WO2008037568A3 PCT/EP2007/059207 EP2007059207W WO2008037568A3 WO 2008037568 A3 WO2008037568 A3 WO 2008037568A3 EP 2007059207 W EP2007059207 W EP 2007059207W WO 2008037568 A3 WO2008037568 A3 WO 2008037568A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hydrogen
- group
- compounds
- detectable group
- detectable
- Prior art date
Links
Classifications
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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
- C07H19/06—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
-
- 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
Abstract
The invention relates to compounds of general structure (I) or salts thereof, wherein B is a nucleobase, X and Y independently are oxygen or sulphur, Z is a chemical group characterized by strong electron withdrawing properties, R1 is hydrogen, hydroxyl or a protected hydroxyl, R2 and R3 are together or separately hydrogen or a hydrocarbyl, R4 is hydrogen or a chemical moiety consisting of a linker molecule L, linking a detectable group to the rest of the structure (I), R5 is hydrogen or an additional electron withdrawing group. R5 can be identical with Z or different. R6 is hydrogen or a chemical moiety consisting of a linker unit L, a cleavable group and a detectable group joined together in the following order R6 = -L-cleavable group-detectable group. The detectable group is placed either on R4 or R6 or is absent, thus either R4 is hydrogen and the detectable group is placed on R6, or R6 is hydrogen and the detectable group is placed on R4, or both R4 and R6 are hydrogen. Numbers m and n are independently 0 or 1. Compounds of formula (I) are useful as reversible chain extension terminators. The invention also relates to the use of the compounds (I) in nucleic acid sequencing as well as to a method of preparing compounds of Formula (I).
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US82445306P | 2006-09-04 | 2006-09-04 | |
US60/824,453 | 2006-09-04 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2008037568A2 WO2008037568A2 (en) | 2008-04-03 |
WO2008037568A3 true WO2008037568A3 (en) | 2008-10-02 |
Family
ID=39230564
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2007/059207 WO2008037568A2 (en) | 2006-09-04 | 2007-09-04 | Reversible terminators for efficient sequencing by synthesis |
Country Status (1)
Country | Link |
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WO (1) | WO2008037568A2 (en) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2294076B1 (en) | 2008-05-27 | 2017-03-08 | TriLink BioTechnologies | Chemically modified nucleoside 5'-triphosphates for thermally initiated replication of nucleic acid |
US9150896B2 (en) | 2012-09-06 | 2015-10-06 | Illumina, Inc. | Nucleotides and primers with removable blocking groups |
US9146248B2 (en) | 2013-03-14 | 2015-09-29 | Intelligent Bio-Systems, Inc. | Apparatus and methods for purging flow cells in nucleic acid sequencing instruments |
US9591268B2 (en) | 2013-03-15 | 2017-03-07 | Qiagen Waltham, Inc. | Flow cell alignment methods and systems |
US10059929B2 (en) | 2014-10-20 | 2018-08-28 | Molecular Assemblies, Inc. | Modified template-independent enzymes for polydeoxynucleotide synthesis |
US9868947B2 (en) | 2015-05-04 | 2018-01-16 | Washington University | Compositions and methods for the construction of a random allelic series |
WO2017058953A1 (en) | 2015-09-28 | 2017-04-06 | The Trustees Of Columbia University In The City Of New York | Design and synthesis of novel disulfide linker based nucleotides as reversible terminators for dna sequencing by synthesis |
WO2018165207A1 (en) | 2017-03-06 | 2018-09-13 | Singular Genomic Systems, Inc. | Nucleic acid sequencing-by-synthesis (sbs) methods that combine sbs cycle steps |
CA3107758A1 (en) | 2018-08-10 | 2020-02-13 | Life Technologies Corporation | Silicon-substituted rhodamine dyes and dye conjugates |
EP3870593A4 (en) | 2018-10-25 | 2022-11-16 | Singular Genomics Systems, Inc. | Nucleotide analogues |
CN113453692A (en) | 2019-01-08 | 2021-09-28 | 奇异基因组学系统公司 | Nucleotide cleavable linkers and uses thereof |
AU2020407267A1 (en) | 2019-12-18 | 2022-06-16 | F. Hoffmann-La Roche Ag | Methods of sequencing by synthesis using a consecutive labeling scheme |
US20240067673A1 (en) * | 2020-10-21 | 2024-02-29 | Big Shenzhen | Modified nucleoside or nucleotide |
US20220145345A1 (en) | 2020-11-11 | 2022-05-12 | Microsoft Technology Licensing, Llc | Spatial control of polynucleotide synthesis by strand capping |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5302509A (en) * | 1989-08-14 | 1994-04-12 | Beckman Instruments, Inc. | Method for sequencing polynucleotides |
WO2001025247A1 (en) * | 1999-10-05 | 2001-04-12 | Quiatech Ab | Compounds for protecting hydroxyls and methods for their use |
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 |
WO2004018497A2 (en) * | 2002-08-23 | 2004-03-04 | Solexa Limited | Modified nucleotides for polynucleotide sequencing |
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2007
- 2007-09-04 WO PCT/EP2007/059207 patent/WO2008037568A2/en active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5302509A (en) * | 1989-08-14 | 1994-04-12 | Beckman Instruments, Inc. | Method for sequencing polynucleotides |
WO2001025247A1 (en) * | 1999-10-05 | 2001-04-12 | Quiatech Ab | Compounds for protecting hydroxyls and methods for their use |
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 |
WO2004018497A2 (en) * | 2002-08-23 | 2004-03-04 | Solexa Limited | Modified nucleotides for polynucleotide sequencing |
Non-Patent Citations (3)
Title |
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OHGI T ET AL: "A New RNA Synthetic Method with a 2'-O-(2-Cyanoethoxymethyl) Protecting Group", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, COLUMBUS, OH; US, vol. 7, no. 16, 1 January 2005 (2005-01-01), pages 3477 - 3480, XP003009345, ISSN: 1523-7060 * |
SANEYOSHI H ET AL: "A General Method for the Synthesis of 2'-O-Cyanoethylated Oligoribonucleotides Having Promising Hybridization Affinity for DNA and RNA and Enhanced Nuclease Resistance", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, vol. 70, no. 25, 1 January 2005 (2005-01-01), pages 10453 - 10460, XP003017305, ISSN: 0022-3263 * |
UMEMOTO T ET AL: "Oligoribonucleotide synthesis by the use of 1-(2-cyanoethoxy)ethyl (CEE) as a 2'-hydroxy protecting group", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, vol. 45, no. 52, 20 December 2004 (2004-12-20), pages 9529 - 9531, XP004727393, ISSN: 0040-4039 * |
Also Published As
Publication number | Publication date |
---|---|
WO2008037568A2 (en) | 2008-04-03 |
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