JP2020536524A5 - - Google Patents
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- Publication number
- JP2020536524A5 JP2020536524A5 JP2020518080A JP2020518080A JP2020536524A5 JP 2020536524 A5 JP2020536524 A5 JP 2020536524A5 JP 2020518080 A JP2020518080 A JP 2020518080A JP 2020518080 A JP2020518080 A JP 2020518080A JP 2020536524 A5 JP2020536524 A5 JP 2020536524A5
- Authority
- JP
- Japan
- Prior art keywords
- molecule
- click
- methyl
- triazole
- catalyst
- 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
- 238000000034 method Methods 0.000 claims 12
- 239000012190 activator Substances 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- 239000003054 catalyst Substances 0.000 claims 8
- 238000006243 chemical reaction Methods 0.000 claims 7
- 125000000524 functional group Chemical group 0.000 claims 7
- 238000012650 click reaction Methods 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 239000011541 reaction mixture Substances 0.000 claims 6
- 150000001768 cations Chemical class 0.000 claims 5
- 239000003446 ligand Substances 0.000 claims 5
- 239000002184 metal Substances 0.000 claims 5
- 239000003960 organic solvent Substances 0.000 claims 5
- VAKXPQHQQNOUEZ-UHFFFAOYSA-N 3-[4-[[bis[[1-(3-hydroxypropyl)triazol-4-yl]methyl]amino]methyl]triazol-1-yl]propan-1-ol Chemical compound N1=NN(CCCO)C=C1CN(CC=1N=NN(CCCO)C=1)CC1=CN(CCCO)N=N1 VAKXPQHQQNOUEZ-UHFFFAOYSA-N 0.000 claims 4
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 4
- MGQYHUDOWOGSQI-UHFFFAOYSA-N 2-[4-[[bis[(1-tert-butyltriazol-4-yl)methyl]amino]methyl]triazol-1-yl]acetic acid Chemical compound N1=NN(C(C)(C)C)C=C1CN(CC=1N=NN(C=1)C(C)(C)C)CC1=CN(CC(O)=O)N=N1 MGQYHUDOWOGSQI-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 230000000087 stabilizing effect Effects 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- WMEZDVILBKIODK-UHFFFAOYSA-N C(C)(C)(C)N1N=NC(=C1)CN(CC=1N=NN(C=1)C(C)(C)C)CC=1N=NN(C=1)CCCS(=O)(=O)O Chemical compound C(C)(C)(C)N1N=NC(=C1)CN(CC=1N=NN(C=1)C(C)(C)C)CC=1N=NN(C=1)CCCS(=O)(=O)O WMEZDVILBKIODK-UHFFFAOYSA-N 0.000 claims 2
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 claims 2
- 239000007983 Tris buffer Substances 0.000 claims 2
- 125000002355 alkine group Chemical group 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000003729 nucleotide group Chemical group 0.000 claims 2
- 150000003852 triazoles Chemical class 0.000 claims 2
- -1 (1-benzyl-4-triazolyl) methyl Chemical group 0.000 claims 1
- 230000004544 DNA amplification Effects 0.000 claims 1
- 238000001712 DNA sequencing Methods 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 108091034117 Oligonucleotide Proteins 0.000 claims 1
- 238000003559 RNA-seq method Methods 0.000 claims 1
- 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 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 239000000872 buffer Substances 0.000 claims 1
- 239000012876 carrier material Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000002372 labelling Methods 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 150000007523 nucleic acids Chemical class 0.000 claims 1
- 108020004707 nucleic acids Proteins 0.000 claims 1
- 102000039446 nucleic acids Human genes 0.000 claims 1
- 239000002777 nucleoside Substances 0.000 claims 1
- 125000003835 nucleoside group Chemical group 0.000 claims 1
- 239000002773 nucleotide Substances 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 235000000346 sugar Nutrition 0.000 claims 1
- 150000008163 sugars Chemical class 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17194093.5A EP3461832A1 (en) | 2017-09-29 | 2017-09-29 | Click based ligation |
| EP17194093.5 | 2017-09-29 | ||
| EP18164071.5 | 2018-03-26 | ||
| EP18164071 | 2018-03-26 | ||
| PCT/EP2018/076495 WO2019063803A1 (en) | 2017-09-29 | 2018-09-28 | LIGATURE BASED ON A CLICK REACTION |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2020536524A JP2020536524A (ja) | 2020-12-17 |
| JP2020536524A5 true JP2020536524A5 (enExample) | 2021-11-04 |
Family
ID=63683912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020518080A Pending JP2020536524A (ja) | 2017-09-29 | 2018-09-28 | クリックベースのライゲーション |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20200361984A1 (enExample) |
| EP (1) | EP3688004A1 (enExample) |
| JP (1) | JP2020536524A (enExample) |
| KR (1) | KR20200057708A (enExample) |
| CN (1) | CN111183144A (enExample) |
| AU (1) | AU2018338781B2 (enExample) |
| BR (1) | BR112020004041A2 (enExample) |
| CA (1) | CA3070514A1 (enExample) |
| WO (1) | WO2019063803A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL290043B2 (en) | 2019-12-23 | 2023-11-01 | Baseclick Gmbh | Method of amplifying mrnas and for preparing full length mrna libraries |
| EP3842532A1 (en) | 2019-12-23 | 2021-06-30 | baseclick GmbH | Method of amplifying mrnas and for preparing full length mrna libraries |
| IL296426A (en) | 2020-03-19 | 2022-11-01 | Baseclick Gmbh | Maran"im that underwent a change for the development of a component |
| EP4046651A1 (en) | 2021-02-23 | 2022-08-24 | baseclick GmbH | Method for producing an mrna tumor vaccine |
| WO2023194331A1 (en) | 2022-04-04 | 2023-10-12 | Ecole Polytechnique Federale De Lausanne (Epfl) | CONSTRUCTION OF SEQUENCING LIBRARIES FROM A RIBONUCLEIC ACID (RNA) USING TAILING AND LIGATION OF cDNA (TLC) |
| EP4585695A1 (en) * | 2024-01-15 | 2025-07-16 | Leica Microsystems CMS GmbH | Label and marker for analysing a biological sample |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA973642B (en) * | 1996-04-26 | 1997-11-25 | Merck & Co Inc | DNA vaccine formulations. |
| ATE469135T1 (de) * | 2002-05-30 | 2010-06-15 | Scripps Research Inst | Kupferkatalysierte ligierung von aziden und acetylenen |
| US8114636B2 (en) * | 2006-02-10 | 2012-02-14 | Life Technologies Corporation | Labeling and detection of nucleic acids |
| GB0706243D0 (en) * | 2007-03-30 | 2007-05-09 | Univ Southampton | Modified nucleic acids |
| EP2239053A1 (en) * | 2009-04-09 | 2010-10-13 | baseclick GmbH | Click chemistry on heterogeneous catalysts |
| WO2010131745A1 (ja) * | 2009-05-15 | 2010-11-18 | 独立行政法人理化学研究所 | 18ｆ標識アジド化合物、18ｆ標識化用試薬及びそれを用いたアルキン化合物の18ｆ標識方法 |
| US20110210017A1 (en) * | 2010-03-01 | 2011-09-01 | Lai Rebecca Y | Fabrication of electrochemical biosensors via click chemistry |
| US20130046083A1 (en) * | 2011-08-16 | 2013-02-21 | Tom Brown | Oligonucleotide ligation |
| WO2014016202A1 (en) * | 2012-07-22 | 2014-01-30 | Universität Basel | Methods for catalytic alkylation of nucleic acids |
| EP2940150A1 (en) * | 2014-04-29 | 2015-11-04 | Baseclick GmbH | Self-assembly of DNA Origami: a new diganostic tool |
| WO2016196492A1 (en) * | 2015-06-01 | 2016-12-08 | Occidental College | Methods, compositions, and kits using heterogeneous catalysts |
| US10155797B2 (en) * | 2015-09-11 | 2018-12-18 | The Governors Of The University Of Alberta | Binding-induced DNA nanomachines |
-
2018
- 2018-09-28 KR KR1020207007632A patent/KR20200057708A/ko not_active Ceased
- 2018-09-28 WO PCT/EP2018/076495 patent/WO2019063803A1/en not_active Ceased
- 2018-09-28 CN CN201880062888.8A patent/CN111183144A/zh active Pending
- 2018-09-28 JP JP2020518080A patent/JP2020536524A/ja active Pending
- 2018-09-28 AU AU2018338781A patent/AU2018338781B2/en active Active
- 2018-09-28 EP EP18778490.5A patent/EP3688004A1/en active Pending
- 2018-09-28 BR BR112020004041-0A patent/BR112020004041A2/pt unknown
- 2018-09-28 US US16/651,450 patent/US20200361984A1/en not_active Abandoned
- 2018-09-28 CA CA3070514A patent/CA3070514A1/en active Pending
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