NO783721L - Fremgangsmaate til syntese av oligonucleotider - Google Patents

Fremgangsmaate til syntese av oligonucleotider

Info

Publication number: NO783721L
Authority: NO; Norway
Prior art keywords: group; compound; labile; chlorophenyl; basic medium
Prior art date: 1977-11-08

Application number

NO783721A

Other languages

English (en)

Norwegian (no)

Inventor

Keiichi Itakura

Original Assignee

Genentech Inc

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.)

1977-11-08

Filing date

1978-11-06

Publication date

1979-05-09

1978-11-06 Application filed by Genentech Inc filed Critical Genentech Inc

1979-05-09 Publication of NO783721L publication Critical patent/NO783721L/no

Links

238000000034 method Methods 0.000 title claims abstract description 58
238000003786 synthesis reaction Methods 0.000 title claims abstract description 20
230000015572 biosynthetic process Effects 0.000 title claims abstract description 18
150000001875 compounds Chemical class 0.000 claims description 34
239000002773 nucleotide Substances 0.000 claims description 24
125000003729 nucleotide group Chemical group 0.000 claims description 24
238000005859 coupling reaction Methods 0.000 claims description 22
-1 tetrahydropyrenyl Chemical group 0.000 claims description 16
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 12
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 12
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
239000007822 coupling agent Substances 0.000 claims description 11
239000011541 reaction mixture Substances 0.000 claims description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
230000008878 coupling Effects 0.000 claims description 8
238000010168 coupling process Methods 0.000 claims description 8
229910019142 PO4 Inorganic materials 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
239000010452 phosphate Substances 0.000 claims description 7
229930024421 Adenine Natural products 0.000 claims description 6
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 6
229960000643 adenine Drugs 0.000 claims description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
229940104302 cytosine Drugs 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000000962 organic group Chemical group 0.000 claims description 6
229940113082 thymine Drugs 0.000 claims description 6
230000002378 acidificating effect Effects 0.000 claims description 5
150000001793 charged compounds Chemical class 0.000 claims description 5
239000002777 nucleoside Substances 0.000 claims description 5
150000003833 nucleoside derivatives Chemical class 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
238000000926 separation method Methods 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
239000002157 polynucleotide Substances 0.000 claims description 2
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
102000040430 polynucleotide Human genes 0.000 claims 1
108091033319 polynucleotide Proteins 0.000 claims 1
238000002601 radiography Methods 0.000 claims 1
108091034117 Oligonucleotide Proteins 0.000 abstract description 21
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 abstract description 15
150000005691 triesters Chemical class 0.000 abstract description 13
239000000047 product Substances 0.000 description 22
108020004414 DNA Proteins 0.000 description 14
102000053602 DNA Human genes 0.000 description 14
239000013638 trimer Substances 0.000 description 12
239000000376 reactant Substances 0.000 description 11
125000006239 protecting group Chemical group 0.000 description 10
229940124276 oligodeoxyribonucleotide Drugs 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
150000005690 diesters Chemical class 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
238000000746 purification Methods 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
150000001413 amino acids Chemical class 0.000 description 4
239000012634 fragment Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
125000003277 amino group Chemical group 0.000 description 3
230000008901 benefit Effects 0.000 description 3
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 3
229940092714 benzenesulfonic acid Drugs 0.000 description 3
239000013612 plasmid Substances 0.000 description 3
229920001184 polypeptide Polymers 0.000 description 3
108090000765 processed proteins & peptides Proteins 0.000 description 3
102000004196 processed proteins & peptides Human genes 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
DVMMLSHVYSHICM-MUWCNIOGSA-N (dT)15 Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(O)=O)[C@@H](O)C1 DVMMLSHVYSHICM-MUWCNIOGSA-N 0.000 description 2
108020004705 Codon Proteins 0.000 description 2
GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
239000000539 dimer Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000008101 lactose Substances 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
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 1
DTWKBHYZSSXPJO-UHFFFAOYSA-N 2-(benzenesulfonyl)-5-nitro-1h-imidazole Chemical compound [O-][N+](=O)C1=CNC(S(=O)(=O)C=2C=CC=CC=2)=N1 DTWKBHYZSSXPJO-UHFFFAOYSA-N 0.000 description 1
125000002103 4,4'-dimethoxytriphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)(C1=C([H])C([H])=C(OC([H])([H])[H])C([H])=C1[H])C1=C([H])C([H])=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
MMRDVCBJYHBQOX-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)C1=[C-]N=NN1 Chemical compound C1(=CC=CC=C1)S(=O)(=O)C1=[C-]N=NN1 MMRDVCBJYHBQOX-UHFFFAOYSA-N 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
108010054278 Lac Repressors Proteins 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
WPPONCHFOIIFIJ-UHFFFAOYSA-N N1N=NN=[C-]1 Chemical compound N1N=NN=[C-]1 WPPONCHFOIIFIJ-UHFFFAOYSA-N 0.000 description 1
108091028664 Ribonucleotide Proteins 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229960001456 adenosine triphosphate Drugs 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000005547 deoxyribonucleotide Substances 0.000 description 1
125000002637 deoxyribonucleotide group Chemical group 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000001502 gel electrophoresis Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
230000000873 masking effect Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000003835 nucleoside group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000813 peptide hormone Substances 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
150000004713 phosphodiesters Chemical class 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000002336 ribonucleotide Substances 0.000 description 1
125000002652 ribonucleotide group Chemical group 0.000 description 1
238000005055 short column chromatography Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
230000009466 transformation Effects 0.000 description 1
239000002435 venom Substances 0.000 description 1
210000001048 venom Anatomy 0.000 description 1
231100000611 venom Toxicity 0.000 description 1

Classifications

- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Saccharide Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

NO783721A 1977-11-08 1978-11-06 Fremgangsmaate til syntese av oligonucleotider NO783721L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US84960877A	1977-11-08	1977-11-08

Publications (1)

Publication Number	Publication Date
NO783721L true NO783721L (no)	1979-05-09

Family

ID=25306107

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO783721A NO783721L (no)	1977-11-08	1978-11-06	Fremgangsmaate til syntese av oligonucleotider

Country Status (22)

Country	Link
EP (1)	EP0002322A3 (fr)
JP (1)	JPS5473787A (fr)
AU (1)	AU4136078A (fr)
BE (1)	BE871781A (fr)
BR (1)	BR7807288A (fr)
DD (1)	DD141836A5 (fr)
DE (1)	DE2848054A1 (fr)
DK (1)	DK493678A (fr)
ES (1)	ES474850A1 (fr)
FI (1)	FI783364A7 (fr)
FR (1)	FR2407939A1 (fr)
GB (1)	GB2007670A (fr)
IL (1)	IL55893A0 (fr)
LU (1)	LU80483A1 (fr)
NL (1)	NL7811043A (fr)
NO (1)	NO783721L (fr)
OA (1)	OA06003A (fr)
PL (1)	PL210786A1 (fr)
PT (1)	PT68754A (fr)
SE (1)	SE7811459L (fr)
ZA (1)	ZA786303B (fr)
ZM (1)	ZM9478A1 (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RO80052B (ro) *	1977-11-08	1985-03-30	Genetech	Procedeu pentru prepararea unui vehicul recombinat de clonare pentru transformarea unei gazde bacteriene pentru a deveni generator de polipeptida heterologa
US4342832A (en) *	1979-07-05	1982-08-03	Genentech, Inc.	Method of constructing a replicable cloning vehicle having quasi-synthetic genes
US4474947A (en) *	1982-04-08	1984-10-02	Biosearch	Benzazolides and their employment in phosphate ester oligonucleotide synthesis processes
JPS61152695A (ja) *	1984-12-26	1986-07-11	Nippon Shinyaku Co Ltd	長鎖ｄｎａの合成法
SG171914A1 (en)	2008-12-02	2011-07-28	Chiralgen Ltd	Method for the synthesis of phosphorus atom modified nucleic acids
EP2451461A4 (fr)	2009-07-06	2013-05-29	Ontorii Inc	Nouveaux précurseurs d'acide nucléique et leurs méthodes d'utilisation
DK2620428T3 (da)	2010-09-24	2019-07-01	Wave Life Sciences Ltd	Asymmetrisk hjælpegruppe
US9605019B2 (en)	2011-07-19	2017-03-28	Wave Life Sciences Ltd.	Methods for the synthesis of functionalized nucleic acids
CN112007045B (zh)	2012-07-13	2026-01-06	波涛生命科学有限公司	手性控制
JP6246121B2 (ja)	2012-07-13	2017-12-13	株式会社新日本科学	キラル核酸アジュバント
DK2872485T3 (da)	2012-07-13	2021-03-08	Wave Life Sciences Ltd	Asymmetrisk hjælpegruppe
WO2015108048A1 (fr)	2014-01-15	2015-07-23	株式会社新日本科学	Adjuvant d'acide nucléique chiral ayant un effet antitumoral et agent antitumoral
US10322173B2 (en)	2014-01-15	2019-06-18	Shin Nippon Biomedical Laboratories, Ltd.	Chiral nucleic acid adjuvant having anti-allergic activity, and anti-allergic agent
EP3095461A4 (fr)	2014-01-15	2017-08-23	Shin Nippon Biomedical Laboratories, Ltd.	Adjuvant d'acide nucléique chiral possédant une activité d'induction d'immunité, et activateur d'induction d'immunité
KR102423317B1 (ko)	2014-01-16	2022-07-22	웨이브 라이프 사이언시스 리미티드	키랄 디자인

1978
- 1978-09-06 BR BR7807288A patent/BR7807288A/pt unknown
- 1978-11-06 NL NL7811043A patent/NL7811043A/xx not_active Application Discontinuation
- 1978-11-06 JP JP13721478A patent/JPS5473787A/ja active Pending
- 1978-11-06 GB GB7843445A patent/GB2007670A/en not_active Withdrawn
- 1978-11-06 DK DK493678A patent/DK493678A/da unknown
- 1978-11-06 AU AU41360/78A patent/AU4136078A/en active Pending
- 1978-11-06 NO NO783721A patent/NO783721L/no unknown
- 1978-11-06 DE DE19782848054 patent/DE2848054A1/de not_active Withdrawn
- 1978-11-06 SE SE7811459A patent/SE7811459L/xx unknown
- 1978-11-06 EP EP78300595A patent/EP0002322A3/fr not_active Withdrawn
- 1978-11-06 ES ES474850A patent/ES474850A1/es not_active Expired
- 1978-11-06 FI FI783364A patent/FI783364A7/fi unknown
- 1978-11-06 IL IL55893A patent/IL55893A0/xx unknown
- 1978-11-06 BE BE1009120A patent/BE871781A/fr unknown
- 1978-11-06 FR FR7831349A patent/FR2407939A1/fr not_active Withdrawn
- 1978-11-07 DD DD78208919A patent/DD141836A5/de unknown
- 1978-11-07 PT PT68754A patent/PT68754A/pt unknown
- 1978-11-08 ZM ZM94/78A patent/ZM9478A1/xx unknown
- 1978-11-08 ZA ZA00786303A patent/ZA786303B/xx unknown
- 1978-11-08 OA OA56653A patent/OA06003A/fr unknown
- 1978-11-08 LU LU80483A patent/LU80483A1/fr unknown
- 1978-11-08 PL PL21078678A patent/PL210786A1/xx unknown

Also Published As

Publication number	Publication date
EP0002322A3 (fr)	1979-06-27
DE2848054A1 (de)	1979-05-10
LU80483A1 (fr)	1979-03-22
NL7811043A (nl)	1979-05-10
JPS5473787A (en)	1979-06-13
BR7807288A (pt)	1979-06-12
IL55893A0 (en)	1979-01-31
PT68754A (en)	1978-12-01
SE7811459L (sv)	1979-05-09
FI783364A7 (fi)	1979-05-09
OA06003A (fr)	1981-06-30
PL210786A1 (pl)	1979-07-16
BE871781A (fr)	1979-05-07
ZA786303B (en)	1979-10-31
AU4136078A (en)	1979-05-17
GB2007670A (en)	1979-05-23
EP0002322A2 (fr)	1979-06-13
ES474850A1 (es)	1979-12-01
DD141836A5 (de)	1980-05-21
ZM9478A1 (en)	1980-03-21
FR2407939A1 (fr)	1979-06-01
DK493678A (da)	1979-07-12

Publication	Publication Date	Title
Kierzek et al.	1986	Polymer-supported RNA synthesis and its application to test the nearest-neighbor model for duplex stability
Zhou et al.	2021	Development of kilogram-scale convergent liquid-phase synthesis of oligonucleotides
Mag et al.	1991	Synthesis and selective cleavage of an oligodeoxynucleotide containing a bridged intemucleotide 5′-phosphorothioate linkage
EP1409497B1 (fr)	2005-01-19	Elaboration de phosphoramidites d'acide nucleique verrouille
SG11202110045PA (en)	2021-10-28	Technologies useful for oligonucleotide preparation
EP0830366B1 (fr)	2000-07-05	Procedes ameliores de synthese d'oligonucleotides
CA1155442A (fr)	1983-10-18	Agent de combinaison nucleosidique et methodes
US5264566A (en)	1993-11-23	Method for in vitro oligonucleotide synthesis using H-phosphonates
CA2330192A1 (fr)	1999-12-09	Activateurs pour la synthese d'oligonucleotides
EP0002322A2 (fr)	1979-06-13	Procédé "Triester" amélioré pour la synthèse d'oligonucléotides
JPH03501128A (ja)	1991-03-14	ヌクレオシドおよびポリヌクレオチドチオホスホラミダイトおよびホスホロジチオエイト化合物並びに方法
Ohtsuka et al.	1978	Studies on transfer ribonucleic acids and related compounds. 20. A new versatile ribooligonucleotide block with 2'-(o-nitrobenzyl) and 3'-phosphorodianilidate groups suitable for elongation of chains in the 3'and 5'directions
EP0948514B1 (fr)	2005-04-27	Procede de synthese de phosphoramidites nucleotidiques ou oligonucleotidiques
Miura et al.	1987	Blockwise mechanical synthesis of oligonucleotides by the phosphoramidite method
EP1317466B1 (fr)	2005-02-23	Synthons destines a la synthese d'oligonucleotides
Ohtsuka et al.	1979	Studies on transfer ribonucleic acids and related compounds. 29. Synthesis of a decaribonucleotide of Escherichia coli tRNAfMet (bases 11-20) using a new phosphorylating reagent
US5134228A (en)	1992-07-28	Nucleoside-3'-phosphites for synthesis of oligonucleotides
Rozners et al.	1992	Synthesis of Oligoribonucleotides by the H-Phosphonate Approach Using Base Labile 2′-O-Protecting Groups. V. Recent Progress in Development of the Method
Van Boom et al.	1977	Synthesis of oltgonucleotides with sequences identical with or analogous to the 3′-end of 16S ribosomal RNA of Es cherichia coli: preparation of m62A-CCUCC and ACCUC-m42C via phosphotriester intermediates1
US6124484A (en)	2000-09-26	Recovery of triarylmethyl halide protecting groups cleaved during oligonucleotide synthesis
Nagyváry	1966	Studies on the specific synthesis of the natural internucleotide linkage by the use of cyclonucleosides. I. The Utilization of Unprotected Nucleotides
Kakuta et al.	2023	Solid-phase synthesis of oligodeoxynucleotides using nucleobase N-unprotected oxazaphospholidine derivatives bearing a long alkyl chain
Takaku et al.	1981	4-Chlorophenyl 5-chloro-8-quinolyl phosphorotetrazolide: A highly efficient phosphorylating agent for oligoribonucleotide synthesis.
SU608805A1 (ru)	1978-05-30	Способ получени нуклеозид-5-диили тирфосфатов
Sekine et al.	1988	Synthesis of oligoribonucleotides by use of 4, 4', 4"-tris (acyloxy) trityl groups for protection of the 6-amino group of adenosine.