JPH0359914B2 - - Google Patents
Info
- Publication number
- JPH0359914B2 JPH0359914B2 JP59501526A JP50152684A JPH0359914B2 JP H0359914 B2 JPH0359914 B2 JP H0359914B2 JP 59501526 A JP59501526 A JP 59501526A JP 50152684 A JP50152684 A JP 50152684A JP H0359914 B2 JPH0359914 B2 JP H0359914B2
- Authority
- JP
- Japan
- Prior art keywords
- dmt
- benzoyl
- reaction
- nucleotide
- dimethoxytrityl
- 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.)
- Expired - Lifetime
Links
- 108091034117 Oligonucleotide Proteins 0.000 description 88
- 238000000034 method Methods 0.000 description 82
- 125000003729 nucleotide group Chemical group 0.000 description 81
- 239000002773 nucleotide Substances 0.000 description 68
- 125000006853 reporter group Chemical group 0.000 description 67
- 239000002585 base Substances 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 66
- 239000000047 product Substances 0.000 description 65
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 239000002777 nucleoside Substances 0.000 description 49
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical group NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 42
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- 239000007787 solid Substances 0.000 description 40
- 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 39
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 38
- 238000003786 synthesis reaction Methods 0.000 description 38
- -1 nucleoside triphosphates Chemical class 0.000 description 34
- 125000001424 substituent group Chemical group 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 32
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 28
- 239000000178 monomer Substances 0.000 description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 25
- 230000000873 masking effect Effects 0.000 description 25
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- 150000003833 nucleoside derivatives Chemical class 0.000 description 23
- 229940104302 cytosine Drugs 0.000 description 21
- 108091033319 polynucleotide Proteins 0.000 description 20
- 102000040430 polynucleotide Human genes 0.000 description 20
- 125000003835 nucleoside group Chemical group 0.000 description 19
- 239000002157 polynucleotide Substances 0.000 description 19
- 229940035893 uracil Drugs 0.000 description 17
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 14
- 238000005859 coupling reaction Methods 0.000 description 14
- 239000003446 ligand Substances 0.000 description 14
- 238000006911 enzymatic reaction Methods 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 12
- 238000011282 treatment Methods 0.000 description 12
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical class NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 11
- 108020004414 DNA Proteins 0.000 description 11
- 238000001514 detection method Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 230000002285 radioactive effect Effects 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 10
- 239000002243 precursor Substances 0.000 description 10
- 150000003141 primary amines Chemical class 0.000 description 10
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical group N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 9
- 229930024421 Adenine Natural products 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229960000643 adenine Drugs 0.000 description 9
- 230000003993 interaction Effects 0.000 description 9
- 230000004048 modification Effects 0.000 description 9
- 238000012986 modification Methods 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 150000007523 nucleic acids Chemical group 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- LOSXTWDYAWERDB-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-2,3-dimethoxybenzene Chemical compound COC1=CC=CC(C(Cl)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1OC LOSXTWDYAWERDB-UHFFFAOYSA-N 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 230000000295 complement effect Effects 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 238000009396 hybridization Methods 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 102000039446 nucleic acids Human genes 0.000 description 7
- 108020004707 nucleic acids Proteins 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 235000020958 biotin Nutrition 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 125000002652 ribonucleotide group Chemical group 0.000 description 6
- 238000001308 synthesis method Methods 0.000 description 6
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 6
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 description 5
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 108091028664 Ribonucleotide Proteins 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
- 229960002685 biotin Drugs 0.000 description 5
- 239000011616 biotin Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000002637 deoxyribonucleotide group Chemical group 0.000 description 5
- 230000002255 enzymatic effect Effects 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 150000003230 pyrimidines Chemical class 0.000 description 5
- 239000002336 ribonucleotide Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000001226 triphosphate Substances 0.000 description 5
- MXHRCPNRJAMMIM-SHYZEUOFSA-N 2'-deoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 MXHRCPNRJAMMIM-SHYZEUOFSA-N 0.000 description 4
- MBPYSSRDTGXWJD-IVZWLZJFSA-N 2,2,2-trifluoro-n-[3-[1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]prop-2-enyl]acetamide Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(C=CCNC(=O)C(F)(F)F)=C1 MBPYSSRDTGXWJD-IVZWLZJFSA-N 0.000 description 4
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- OIRDTQYFTABQOQ-KQYNXXCUSA-N Adenosine Natural products C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 102000053602 DNA Human genes 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000005547 deoxyribonucleotide Substances 0.000 description 4
- 229960005215 dichloroacetic acid Drugs 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 4
- MHMNJMPURVTYEJ-UHFFFAOYSA-N fluorescein-5-isothiocyanate Chemical compound O1C(=O)C2=CC(N=C=S)=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 MHMNJMPURVTYEJ-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 150000002540 isothiocyanates Chemical group 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 150000003212 purines Chemical class 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 238000013519 translation Methods 0.000 description 4
- 235000011178 triphosphate Nutrition 0.000 description 4
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 3
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 3
- HUDPLKWXRLNSPC-UHFFFAOYSA-N 4-aminophthalhydrazide Chemical compound O=C1NNC(=O)C=2C1=CC(N)=CC=2 HUDPLKWXRLNSPC-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WAQKEWAEFDODPY-UHFFFAOYSA-N 8-n-(6-aminohexyl)-7h-purine-6,8-diamine Chemical group C1=NC(N)=C2NC(NCCCCCCN)=NC2=N1 WAQKEWAEFDODPY-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 102000016911 Deoxyribonucleases Human genes 0.000 description 3
- 108010053770 Deoxyribonucleases Proteins 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920005654 Sephadex Polymers 0.000 description 3
- 239000012507 Sephadex™ Substances 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 150000001615 biotins Chemical class 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000460 chlorine Chemical group 0.000 description 3
- 229910052801 chlorine Chemical group 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- MXHRCPNRJAMMIM-UHFFFAOYSA-N desoxyuridine Natural products C1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 MXHRCPNRJAMMIM-UHFFFAOYSA-N 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 238000003780 insertion Methods 0.000 description 3
- 230000037431 insertion Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000002515 oligonucleotide synthesis Methods 0.000 description 3
- 239000002718 pyrimidine nucleoside Substances 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 229940113082 thymine Drugs 0.000 description 3
- 125000005270 trialkylamine group Chemical group 0.000 description 3
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 description 2
- OALHHIHQOFIMEF-UHFFFAOYSA-N 3',6'-dihydroxy-2',4',5',7'-tetraiodo-3h-spiro[2-benzofuran-1,9'-xanthene]-3-one Chemical group O1C(=O)C2=CC=CC=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 OALHHIHQOFIMEF-UHFFFAOYSA-N 0.000 description 2
- PGAHCHQYHZKNAN-UHFFFAOYSA-N 6-amino-5-(3-aminopropyl)-1h-pyrimidin-2-one Chemical group NCCCC1=CNC(=O)N=C1N PGAHCHQYHZKNAN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 108010017826 DNA Polymerase I Proteins 0.000 description 2
- 102000004594 DNA Polymerase I Human genes 0.000 description 2
- BVTJGGGYKAMDBN-UHFFFAOYSA-N Dioxetane Chemical compound C1COO1 BVTJGGGYKAMDBN-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
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- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- AHUJXUYEELPHRR-UHFFFAOYSA-N pyrimidine;1h-pyrimidine-2,4-dione Chemical compound C1=CN=CN=C1.O=C1C=CNC(=O)N1 AHUJXUYEELPHRR-UHFFFAOYSA-N 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- 235000010339 sodium tetraborate Nutrition 0.000 description 1
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- HDZZVAMISRMYHH-LITAXDCLSA-N tubercidin Chemical compound C1=CC=2C(N)=NC=NC=2N1[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O HDZZVAMISRMYHH-LITAXDCLSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D03—WEAVING
- D03D—WOVEN FABRICS; METHODS OF WEAVING; LOOMS
- D03D47/00—Looms in which bulk supply of weft does not pass through shed, e.g. shuttleless looms, gripper shuttle looms, dummy shuttle looms
- D03D47/34—Handling the weft between bulk storage and weft-inserting means
- D03D47/36—Measuring and cutting the weft
- D03D47/361—Drum-type weft feeding devices
- D03D47/367—Monitoring yarn quantity on the drum
-
- D—TEXTILES; PAPER
- D03—WEAVING
- D03D—WOVEN FABRICS; METHODS OF WEAVING; LOOMS
- D03D47/00—Looms in which bulk supply of weft does not pass through shed, e.g. shuttleless looms, gripper shuttle looms, dummy shuttle looms
- D03D47/34—Handling the weft between bulk storage and weft-inserting means
- D03D47/36—Measuring and cutting the weft
- D03D47/361—Drum-type weft feeding devices
- D03D47/362—Drum-type weft feeding devices with yarn retaining devices, e.g. stopping pins
-
- D—TEXTILES; PAPER
- D03—WEAVING
- D03D—WOVEN FABRICS; METHODS OF WEAVING; LOOMS
- D03D47/00—Looms in which bulk supply of weft does not pass through shed, e.g. shuttleless looms, gripper shuttle looms, dummy shuttle looms
- D03D47/34—Handling the weft between bulk storage and weft-inserting means
- D03D47/36—Measuring and cutting the weft
- D03D47/361—Drum-type weft feeding devices
- D03D47/362—Drum-type weft feeding devices with yarn retaining devices, e.g. stopping pins
- D03D47/363—Construction or control of the yarn retaining devices
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65H—HANDLING THIN OR FILAMENTARY MATERIAL, e.g. SHEETS, WEBS, CABLES
- B65H2557/00—Means for control not provided for in groups B65H2551/00 - B65H2555/00
- B65H2557/30—Control systems architecture or components, e.g. electronic or pneumatic modules; Details thereof
- B65H2557/33—Control systems architecture or components, e.g. electronic or pneumatic modules; Details thereof for digital control, e.g. for generating, counting or comparing pulses
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Looms (AREA)
- Forwarding And Storing Of Filamentary Material (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8205598 | 1982-09-30 | ||
| SE8207098A SE8207098D0 (sv) | 1982-12-10 | 1982-12-10 | Anordning for temporer upplagring och matning av uppmetta garnlengder, foretredesvis till dysvevmaskiner |
| AU83/00254 | 1983-02-22 | ||
| US468498 | 1983-02-22 | ||
| SE8304891A SE8304891D0 (sv) | 1983-09-13 | 1983-09-13 | System for temporer upplagring och matning av uppmetta garnlengder, foretredesvis till dysvevmaskiner |
| SE8305040A SE8305040D0 (sv) | 1983-09-20 | 1983-09-20 | System for temporer upplagring och matning av uppmetta garnlengder, foretredesvis till dys-vevmaskiner |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2197582A Division JP2542453B2 (ja) | 1983-02-22 | 1990-07-23 | 検出可能な１本鎖オリゴヌクレオチドの化学的合成に有用な化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60500717A JPS60500717A (ja) | 1985-05-16 |
| JPH0359914B2 true JPH0359914B2 (pt) | 1991-09-12 |
Family
ID=27484634
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP83503159A Granted JPS59501830A (ja) | 1982-09-30 | 1983-09-30 | 横糸を蓄積、供給および測定する装置および該装置を制御するための方法 |
| JP50152684A Granted JPS60500717A (ja) | 1982-09-30 | 1984-02-22 | リポ−タ−グル−プを含んでいる一定配列の１本鎖オリゴヌクレオチド、およびその化学的合成法 |
| JP28277992A Expired - Lifetime JPH07100900B2 (ja) | 1982-09-30 | 1992-10-21 | 横糸を蓄積、供給および測定する装置を制御するための方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP83503159A Granted JPS59501830A (ja) | 1982-09-30 | 1983-09-30 | 横糸を蓄積、供給および測定する装置および該装置を制御するための方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28277992A Expired - Lifetime JPH07100900B2 (ja) | 1982-09-30 | 1992-10-21 | 横糸を蓄積、供給および測定する装置を制御するための方法 |
Country Status (4)
| Country | Link |
|---|---|
| EP (2) | EP0107110B1 (pt) |
| JP (3) | JPS59501830A (pt) |
| DE (2) | DE3371098D1 (pt) |
| WO (1) | WO1984001394A1 (pt) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8207098D0 (sv) * | 1982-12-10 | 1982-12-10 | Iro Ab | Anordning for temporer upplagring och matning av uppmetta garnlengder, foretredesvis till dysvevmaskiner |
| BE899671A (nl) * | 1984-05-16 | 1984-11-16 | Picanol Nv | Regelbare sturing van de inslagdraad van een weefgetouw. |
| IT1176259B (it) * | 1984-06-04 | 1987-08-18 | Roy Electrotex Spa | Alimentatore di trama per telai di tessitura |
| US4781224A (en) * | 1984-07-20 | 1988-11-01 | Nissan Motor Co., Ltd. | Loom equipped with weft picking control system |
| JPH0639735B2 (ja) * | 1984-07-24 | 1994-05-25 | 日産自動車株式会社 | 流体噴射式織機の制御装置 |
| US4768565A (en) * | 1984-09-27 | 1988-09-06 | Aktiebolaget Iro | Method for controlling a yarn storing, feeding and measuring device |
| DE3440389C1 (de) * | 1984-11-05 | 1986-03-20 | Bernd Dipl-Ing Scheffel | Fadenspeichervorrichtung fuer Webmaschinen und Verfahren zu deren Betrieb |
| IT1215235B (it) * | 1985-01-30 | 1990-01-31 | Omv Off Mecc Vilminore | Dell'alimentazione di filati di dispositivo di autoregolazione trama in telai di tessitura ad aria. |
| JPH0627398B2 (ja) * | 1985-03-30 | 1994-04-13 | 日産自動車株式会社 | 流体噴射式織機の緯入れ装置 |
| JP2509574B2 (ja) * | 1985-08-15 | 1996-06-19 | アモコ・コーポレーション | 標識付けした核酸 |
| CH670263A5 (pt) * | 1986-05-23 | 1989-05-31 | Sulzer Ag | |
| DE3675389D1 (de) * | 1986-05-30 | 1990-12-06 | Iro Ab | Vorrichtung fuer die kontrolle eines schusseintrages. |
| EP0250359B1 (de) * | 1986-06-16 | 1990-01-17 | GebràDer Sulzer Aktiengesellschaft | Schussfadenspeicher für Webmaschine |
| JPS6328944A (ja) * | 1986-07-14 | 1988-02-06 | 津田駒工業株式会社 | よこ入れ装置の測長量設定方法およびその装置 |
| EP0253760B1 (de) * | 1986-07-15 | 1991-11-27 | GebràDer Sulzer Aktiengesellschaft | Verfahren für den Betrieb eines Schussfadenspeichers für eine Webmaschine |
| DE3628485A1 (de) * | 1986-08-22 | 1988-02-25 | Iro Ab | Geraet zum speichern von garn |
| BE905471A (nl) * | 1986-09-23 | 1987-03-23 | Picanol Nv | Werkwijze om bij weefmaschines de lengte van de in de gaap te brengen inslagdraad te regelen en inrichtingen hierbij aangewend. |
| DE8800216U1 (de) * | 1987-11-29 | 1989-03-30 | Aktiebolaget Iro, Ulricehamn | Vorrichtung zum Speichern, Liefern und Messen eines Fadens |
| JPH01321951A (ja) * | 1988-06-03 | 1989-12-27 | Gebr Sulzer Ag | 緯糸蓄積装置 |
| FR2632955B1 (fr) * | 1988-06-20 | 1991-12-27 | Oris Ind | Derives de nucleosides utilisables pour la synthese d'oligonucleotides marques, oligonucleotides obtenus a partir de ces derives et leur synthese |
| EP0561218A1 (de) * | 1992-03-16 | 1993-09-22 | Lindauer Dornier Gesellschaft M.B.H | Verfahren und Vorrichtung zur Bereitstellung einer definierten Schussfadenreserve bei Webstop |
| SE511091C2 (sv) * | 1993-04-21 | 1999-08-02 | Sipra Patent Beteiligung | Garnmatare för textilmaskiner |
| US5800996A (en) * | 1996-05-03 | 1998-09-01 | The Perkin Elmer Corporation | Energy transfer dyes with enchanced fluorescence |
| WO2005103249A1 (ja) | 2004-04-26 | 2005-11-03 | Wako Pure Chemical Industries, Ltd. | 結核菌検出用プライマー及びプローブ、並びにこれを用いたヒト型結核菌の検出方法 |
| ATE496996T1 (de) | 2005-05-13 | 2011-02-15 | Wako Pure Chem Ind Ltd | Primer, sonden, verfahren und verwendungen davon zum nachweis von mycobacterium kansasii |
| JP5239853B2 (ja) | 2006-03-13 | 2013-07-17 | 和光純薬工業株式会社 | 変異遺伝子の検出方法 |
| CN101432426B (zh) | 2006-05-02 | 2012-09-19 | 和光纯药工业株式会社 | 胞内分枝杆菌检测用引物和探针、以及使用该引物和探针的胞内分枝杆菌的检测方法 |
| JPWO2008075520A1 (ja) | 2006-12-18 | 2010-04-08 | 和光純薬工業株式会社 | マイコバクテリウム・アビウム検出用プライマー及びプローブ、並びにこれを用いたマイコバクテリウム・アビウムの検出方法 |
| US20100323365A1 (en) | 2008-02-08 | 2010-12-23 | Tomokazu Ishikawa | Primer and probe for detecting chlamydophila caviae, as well as a chlamydophila caviae detection method using the same |
| WO2009145181A1 (ja) | 2008-05-28 | 2009-12-03 | 和光純薬工業株式会社 | マイコバクテリウム・イントラセルラー検出用プライマー及びプローブ、並びにこれを用いたマイコバクテリウム・イントラセルラーの検出方法 |
| CN102918155B (zh) | 2010-03-23 | 2015-12-16 | 和光纯药工业株式会社 | 沙眼衣原体检测用引物和探针、以及使用该引物和探针的沙眼衣原体的检测方法 |
| JP5648669B2 (ja) * | 2012-10-12 | 2015-01-07 | 株式会社豊田自動織機 | 緯糸測長貯留装置の緯糸送り羽根調整工具 |
| JP6844613B2 (ja) | 2016-03-30 | 2021-03-17 | 富士フイルム和光純薬株式会社 | クラミジア・トラコマティス検出用プライマーセット及びこれを用いたクラミジア・トラコマティス検出方法、並びにそのための試薬キット |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57176998A (en) * | 1981-03-27 | 1982-10-30 | University Patents Inc | Phosphoramidate compound and manufacture |
| JPS57209297A (en) * | 1981-04-17 | 1982-12-22 | Univ Yale | Modified nucleotide, manufacture and use |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH394899A (it) * | 1961-10-31 | 1965-06-30 | Sobrevin Soc De Brevets Ind Et | Apparecchio per la regolazione della tensione all'uscita di un filo nel passaggio dal suo svolgimento al suo avvolgimento |
| CH404575A (de) * | 1963-09-12 | 1965-12-15 | Saurer Ag Adolph | Dosiervorrichtung an Webmaschine |
| JPS5626038A (en) * | 1979-08-10 | 1981-03-13 | Nissan Motor | Weft yarn storage apparatus of shuttleless loom |
| CH647999A5 (de) * | 1980-06-17 | 1985-02-28 | Rueti Ag Maschf | Fadenliefervorrichtung fuer textilmaschinen und verfahren zum betrieb der fadenliefervorrichtung. |
| JPS5782546A (en) * | 1980-11-12 | 1982-05-24 | Nissan Motor | Storage apparatus of "futakoshi" weft yarn of shuttleless loom |
-
1983
- 1983-09-30 EP EP19830109818 patent/EP0107110B1/en not_active Expired
- 1983-09-30 EP EP19840113290 patent/EP0148356B1/en not_active Expired
- 1983-09-30 DE DE8383109818T patent/DE3371098D1/de not_active Expired
- 1983-09-30 WO PCT/EP1983/000254 patent/WO1984001394A1/de unknown
- 1983-09-30 DE DE8484113290T patent/DE3382053D1/de not_active Expired - Lifetime
- 1983-09-30 JP JP83503159A patent/JPS59501830A/ja active Granted
-
1984
- 1984-02-22 JP JP50152684A patent/JPS60500717A/ja active Granted
-
1992
- 1992-10-21 JP JP28277992A patent/JPH07100900B2/ja not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57176998A (en) * | 1981-03-27 | 1982-10-30 | University Patents Inc | Phosphoramidate compound and manufacture |
| JPS57209297A (en) * | 1981-04-17 | 1982-12-22 | Univ Yale | Modified nucleotide, manufacture and use |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59501830A (ja) | 1984-11-01 |
| EP0148356A3 (en) | 1989-02-15 |
| DE3382053D1 (de) | 1991-01-17 |
| EP0148356A2 (en) | 1985-07-17 |
| WO1984001394A1 (en) | 1984-04-12 |
| EP0107110B1 (en) | 1987-04-22 |
| JPS60500717A (ja) | 1985-05-16 |
| JPH07102449A (ja) | 1995-04-18 |
| JPH0555619B2 (pt) | 1993-08-17 |
| EP0107110A1 (en) | 1984-05-02 |
| EP0148356B1 (en) | 1990-12-05 |
| DE3371098D1 (en) | 1987-05-27 |
| JPH07100900B2 (ja) | 1995-11-01 |
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