JPWO2020235658A5 - - Google Patents
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- Publication number
- JPWO2020235658A5 JPWO2020235658A5 JP2021520862A JP2021520862A JPWO2020235658A5 JP WO2020235658 A5 JPWO2020235658 A5 JP WO2020235658A5 JP 2021520862 A JP2021520862 A JP 2021520862A JP 2021520862 A JP2021520862 A JP 2021520862A JP WO2020235658 A5 JPWO2020235658 A5 JP WO2020235658A5
- Authority
- JP
- Japan
- Prior art keywords
- protecting group
- alkyl
- group
- protected
- nucleoside base
- 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.)
- Granted
Links
- 239000002777 nucleoside Substances 0.000 claims description 44
- 125000006239 protecting group Chemical group 0.000 claims description 44
- 150000003833 nucleoside derivatives Chemical group 0.000 claims description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 12
- -1 Methoxyethyl Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 230000007935 neutral effect Effects 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 1
- 230000001012 protector Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000002773 nucleotide Substances 0.000 description 5
- 125000003729 nucleotide group Chemical group 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229960005215 dichloroacetic acid Drugs 0.000 description 2
- 125000006245 phosphate protecting group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 238000002515 oligonucleotide synthesis Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000008300 phosphoramidites Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019095591 | 2019-05-21 | ||
| JP2019095591 | 2019-05-21 | ||
| PCT/JP2020/020203 WO2020235658A1 (ja) | 2019-05-21 | 2020-05-21 | オリゴヌクレオチド合成に用いるマルチフルオラスブロックマーおよびこれを用いたオリゴヌクレオチド合成方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPWO2020235658A1 JPWO2020235658A1 (https=) | 2020-11-26 |
| JPWO2020235658A5 true JPWO2020235658A5 (https=) | 2022-03-15 |
| JP7393807B2 JP7393807B2 (ja) | 2023-12-07 |
Family
ID=73458301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021520862A Active JP7393807B2 (ja) | 2019-05-21 | 2020-05-21 | オリゴヌクレオチド合成に用いるマルチフルオラスブロックマーおよびこれを用いたオリゴヌクレオチド合成方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US12559516B2 (https=) |
| EP (1) | EP3960749B1 (https=) |
| JP (1) | JP7393807B2 (https=) |
| KR (1) | KR102692448B1 (https=) |
| CN (1) | CN113924309A (https=) |
| WO (1) | WO2020235658A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112424213A (zh) | 2018-05-02 | 2021-02-26 | 株式会社纳蒂亚斯 | 寡核苷酸合成用片段及其制造方法、以及使用其的寡核苷酸的合成方法 |
| CN114269764A (zh) * | 2018-05-02 | 2022-04-01 | 株式会社纳蒂亚斯 | 立体控制寡核苷酸合成用光学活性片段及其制造方法、以及使用其的立体控制寡核苷酸的合成方法 |
| EP4293035A4 (en) | 2021-02-12 | 2025-03-05 | Ajinomoto Co., Inc. | METHOD FOR THE PRODUCTION OF OLIGONUCLEOTIDES |
| JPWO2024228396A1 (https=) | 2023-05-01 | 2024-11-07 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4945129B2 (ja) | 2004-01-27 | 2012-06-06 | 株式会社キラルジェン | フルオラス担体およびそれを用いたオリゴヌクレオチド誘導体の製造方法 |
| WO2006040558A1 (en) * | 2004-10-15 | 2006-04-20 | Astrazeneca Ab | Substituted adenines and the use thereof |
| US20060178507A1 (en) | 2004-12-30 | 2006-08-10 | Berry & Associates, Inc. | Fluorous oligonucleotide reagents and affinity purification of oligonucleotides |
| AU2007263728A1 (en) * | 2006-06-27 | 2008-01-03 | Biovitrum Ab (Publ) | Adenosine derivatives for the treatment of pain |
| US20140065223A1 (en) * | 2011-03-31 | 2014-03-06 | Jeanette Libera-Koerner | Perfluorinated compounds for the non-viral transfer of nucleic acids |
| CN108350018A (zh) | 2015-11-17 | 2018-07-31 | 日产化学工业株式会社 | 寡核苷酸的制造方法 |
| WO2018212236A1 (ja) * | 2017-05-16 | 2018-11-22 | 日産化学株式会社 | オリゴヌクレオチドの製造方法 |
| JP7431723B2 (ja) | 2017-08-18 | 2024-02-15 | アジレント・テクノロジーズ・インク | オリゴヌクレオチドのアフィニティー精製のためのオルトエステル組成物 |
| WO2019042888A1 (de) * | 2017-08-27 | 2019-03-07 | Caperis Gmbh | Perfluorierte nukleinsäuren als tenside mit spezifischen eigenschaften |
-
2020
- 2020-05-21 CN CN202080037793.8A patent/CN113924309A/zh active Pending
- 2020-05-21 EP EP20809071.2A patent/EP3960749B1/en active Active
- 2020-05-21 KR KR1020217038369A patent/KR102692448B1/ko active Active
- 2020-05-21 JP JP2021520862A patent/JP7393807B2/ja active Active
- 2020-05-21 US US17/595,613 patent/US12559516B2/en active Active
- 2020-05-21 WO PCT/JP2020/020203 patent/WO2020235658A1/ja not_active Ceased
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