JPH0354113B2 - - Google Patents

Info

Publication number: JPH0354113B2
Authority: JP; Japan
Prior art keywords: minutes; reaction; nucleoside; phosphate; condensing agent
Prior art date: 1982-01-08
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.): Expired

Application number

JP106382A

Other languages

English (en)

Japanese (ja)

Other versions

JPS58118594A (ja

Priority date (The priority date 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 date listed.)

1982-01-08

Filing date

1982-01-08

Publication date

1991-08-19

1982-01-08 Application filed filed Critical

1982-01-08 Priority to JP106382A priority Critical patent/JPS58118594A/ja

1983-07-14 Publication of JPS58118594A publication Critical patent/JPS58118594A/ja

1991-08-19 Publication of JPH0354113B2 publication Critical patent/JPH0354113B2/ja

Status Granted legal-status Critical Current

Links

-1 N-substituted imidazole Chemical class 0.000 claims description 26
239000003795 chemical substances by application Substances 0.000 claims description 15
239000002777 nucleoside Substances 0.000 claims description 12
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
150000003833 nucleoside derivatives Chemical class 0.000 claims description 10
108091034117 Oligonucleotide Proteins 0.000 claims description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 9
239000002773 nucleotide Substances 0.000 claims description 8
125000003729 nucleotide group Chemical group 0.000 claims description 8
229910019142 PO4 Inorganic materials 0.000 claims description 7
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
239000010452 phosphate Substances 0.000 claims description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 2
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 description 22
238000000034 method Methods 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 10
238000006482 condensation reaction Methods 0.000 description 9
239000000047 product Substances 0.000 description 9
125000006239 protecting group Chemical group 0.000 description 8
239000002994 raw material Substances 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000006227 byproduct Substances 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
JAPYIBBSTJFDAK-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)benzenesulfonyl chloride Chemical compound CC(C)C1=CC(C(C)C)=C(S(Cl)(=O)=O)C(C(C)C)=C1 JAPYIBBSTJFDAK-UHFFFAOYSA-N 0.000 description 3
PVJZBZSCGJAWNG-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonyl chloride Chemical compound CC1=CC(C)=C(S(Cl)(=O)=O)C(C)=C1 PVJZBZSCGJAWNG-UHFFFAOYSA-N 0.000 description 3
DUQGAEPCMPBSLE-UHFFFAOYSA-N C1(=C(C(=CC(=C1)C)C)S(=O)(=O)C1=[C-]N(N=N1)[N+](=O)[O-])C Chemical compound C1(=C(C(=CC(=C1)C)C)S(=O)(=O)C1=[C-]N(N=N1)[N+](=O)[O-])C DUQGAEPCMPBSLE-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000007810 chemical reaction solvent Substances 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
150000005691 triesters Chemical class 0.000 description 3
IWDFHWZHHOSSGR-UHFFFAOYSA-N 1-ethylimidazole Chemical compound CCN1C=CN=C1 IWDFHWZHHOSSGR-UHFFFAOYSA-N 0.000 description 2
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
239000000539 dimer Substances 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000000203 mixture Substances 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000003643 water by type Substances 0.000 description 2
BWZHKRSSCFRVIE-UHFFFAOYSA-N 1-n,4-n-dimethyl-2h-pyridine-1,4-diamine Chemical compound CNN1CC=C(NC)C=C1 BWZHKRSSCFRVIE-UHFFFAOYSA-N 0.000 description 1
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
NNYLRQHCYVYNNL-UHFFFAOYSA-N C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)C1=[C-]N(N=N1)[N+](=O)[O-] Chemical compound C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)C1=[C-]N(N=N1)[N+](=O)[O-] NNYLRQHCYVYNNL-UHFFFAOYSA-N 0.000 description 1
AVWFEPDJDKSISU-UHFFFAOYSA-N C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)N1N=NN=[C-]1 Chemical compound C(C)(C)C1=C(C(=CC(=C1)C(C)C)C(C)C)S(=O)(=O)N1N=NN=[C-]1 AVWFEPDJDKSISU-UHFFFAOYSA-N 0.000 description 1
AEFXDGGNILQRDU-UHFFFAOYSA-N C1(=C(C(=CC(=C1)C)C)S(=O)(=O)N1N=NN=[C-]1)C Chemical compound C1(=C(C(=CC(=C1)C)C)S(=O)(=O)N1N=NN=[C-]1)C AEFXDGGNILQRDU-UHFFFAOYSA-N 0.000 description 1
NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical group C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 1
VIHYIVKEECZGOU-UHFFFAOYSA-N N-acetylimidazole Chemical compound CC(=O)N1C=CN=C1 VIHYIVKEECZGOU-UHFFFAOYSA-N 0.000 description 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 description 1
RHFFDWIUKCQFER-UHFFFAOYSA-N [N+](=O)([O-])N1N=NC=[C-]1 Chemical class [N+](=O)([O-])N1N=NC=[C-]1 RHFFDWIUKCQFER-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
238000011088 calibration curve Methods 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229940099352 cholate Drugs 0.000 description 1
BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000005549 deoxyribonucleoside Substances 0.000 description 1
238000001514 detection method Methods 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
125000003835 nucleoside group Chemical group 0.000 description 1
229940124276 oligodeoxyribonucleotide Drugs 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
150000004713 phosphodiesters Chemical group 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000006798 recombination Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000002342 ribonucleoside Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
230000006103 sulfonylation Effects 0.000 description 1
238000005694 sulfonylation reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

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Saccharide Compounds (AREA)

JP106382A 1982-01-08 1982-01-08 縮合剤 Granted JPS58118594A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP106382A JPS58118594A (ja)	1982-01-08	1982-01-08	縮合剤

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP106382A JPS58118594A (ja)	1982-01-08	1982-01-08	縮合剤

Publications (2)

Publication Number	Publication Date
JPS58118594A JPS58118594A (ja)	1983-07-14
JPH0354113B2 true JPH0354113B2 (fr)	1991-08-19

Family

ID=11491072

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP106382A Granted JPS58118594A (ja)	1982-01-08	1982-01-08	縮合剤

Country Status (1)

Country	Link
JP (1)	JPS58118594A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2011146525A3 (fr) *	2010-05-17	2012-04-19	Quality Of Life Essentials, Inc.	Dispositif de couchage portatif

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2009129399A1 (fr) *	2008-04-18	2009-10-22	Dow Global Technologies Inc.	Complexes de sel de silylimidazolium

1982
- 1982-01-08 JP JP106382A patent/JPS58118594A/ja active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2011146525A3 (fr) *	2010-05-17	2012-04-19	Quality Of Life Essentials, Inc.	Dispositif de couchage portatif

Also Published As

Publication number	Publication date
JPS58118594A (ja)	1983-07-14

Publication	Publication Date	Title
US7795423B2 (en)	2010-09-14	Polynucleotide labeling reagent
Mag et al.	1991	Synthesis and selective cleavage of an oligodeoxynucleotide containing a bridged intemucleotide 5′-phosphorothioate linkage
JPS60502102A (ja)	1985-12-05	オリゴヌクレオチドの製造法
CN103237805A (zh)	2013-08-07	寡核糖核苷酸的嵌段合成
WO1993001204A1 (fr)	1993-01-21	Procede et composes de synthese d'arn
DE69609511T2 (de)	2001-03-29	Neue Synthons für die stereoselektive Oligonuklodsynthese
JPH09510206A (ja)	1997-10-14	オリゴヌクレオチドの合成に用いる組成物および方法
US5955600A (en)	1999-09-21	Method for the synthesis of nucleotide or oligonucleotide phosphoramidites
JPH0665280A (ja)	1994-03-08	蛍光標識化合物、その調製法および使用
US12202848B2 (en)	2025-01-21	Phosphoramidite activator
NO783721L (no)	1979-05-09	Fremgangsmaate til syntese av oligonucleotider
CA2421489A1 (fr)	2002-03-14	Synthons destines a la synthese d'oligonucleotides
KR100458979B1 (ko)	2004-12-03	포스포로티오에이트 올리고뉴클레오티드의 합성 방법
JPH0354113B2 (fr)	1991-08-19
US7807821B1 (en)	2010-10-05	Method for the synthesis of nucleic acid without protecting base moiety
JPH0291088A (ja)	1990-03-30	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
US4426517A (en)	1984-01-17	Process for de-cyanoethylating blocked nucleotides
Kakuta et al.	2023	Solid-phase synthesis of oligodeoxynucleotides using nucleobase N-unprotected oxazaphospholidine derivatives bearing a long alkyl chain
JPS5993099A (ja)	1984-05-29	オリゴヌクレオチド誘導体およびその製造法
Nawrot et al.	2002	Bis (hydroxymethyl) phosphinic acid analogues of acyclic nucleosides; synthesis and incorporation into short DNA oligomers
JP2003292499A (ja)	2003-10-15	オリゴヌクレオチドの化学的合成法
KR20100022470A (ko)	2010-03-02	올리고뉴클레오타이드의 합성
JP2003002895A (ja)	2003-01-08	核酸の合成法
US6103891A (en)	2000-08-15	Method for the synthesis of nucleotide or oligonucleotide phosphoramidites
Münch et al.	1997	The (2-Cyano-1-phenyl) ethoxycarbonyl (CPEOC) Group-A New Protecting Group for Oligoribonucleotide Synthesis

JPH0354113B2 - - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=11491072

Family Applications (1)

Country Status (1)

Cited By (1)

Families Citing this family (1)

Cited By (1)

Also Published As

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