CA2276481A1 - Multifunctional linking reagents for synthesis of branched oligomers - Google Patents
Multifunctional linking reagents for synthesis of branched oligomers Download PDFInfo
- Publication number
- CA2276481A1 CA2276481A1 CA002276481A CA2276481A CA2276481A1 CA 2276481 A1 CA2276481 A1 CA 2276481A1 CA 002276481 A CA002276481 A CA 002276481A CA 2276481 A CA2276481 A CA 2276481A CA 2276481 A1 CA2276481 A1 CA 2276481A1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 125000005647 linker group Chemical group 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
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- PEJGGZVVBQPTRG-UHFFFAOYSA-N 3-[2-[2-[2-[bis(4-methoxyphenyl)-phenylmethoxy]ethoxy]ethoxy]ethoxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile Chemical compound C1=CC(OC)=CC=C1C(OCCOCCOCCOP(OCCC#N)N(C(C)C)C(C)C)(C=1C=CC(OC)=CC=1)C1=CC=CC=C1 PEJGGZVVBQPTRG-UHFFFAOYSA-N 0.000 description 1
- QWTBDIBOOIAZEF-UHFFFAOYSA-N 3-[chloro-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile Chemical compound CC(C)N(C(C)C)P(Cl)OCCC#N QWTBDIBOOIAZEF-UHFFFAOYSA-N 0.000 description 1
- RKVHNYJPIXOHRW-UHFFFAOYSA-N 3-bis[di(propan-2-yl)amino]phosphanyloxypropanenitrile Chemical compound CC(C)N(C(C)C)P(N(C(C)C)C(C)C)OCCC#N RKVHNYJPIXOHRW-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- IGPUFFYCAUBNIY-UHFFFAOYSA-N 4-oxopentanoyl 4-oxopentanoate Chemical compound CC(=O)CCC(=O)OC(=O)CCC(C)=O IGPUFFYCAUBNIY-UHFFFAOYSA-N 0.000 description 1
- AYXZIZMZXAORLO-UFLZEWODSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid;1-hydroxypyrrolidine-2,5-dione Chemical compound ON1C(=O)CCC1=O.N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 AYXZIZMZXAORLO-UFLZEWODSA-N 0.000 description 1
- QYICDXXLKSTPLF-UHFFFAOYSA-N 5-aminoheptane-1,3-diol Chemical group CCC(N)CC(O)CCO QYICDXXLKSTPLF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
- AHCYMLUZIRLXAA-SHYZEUOFSA-N Deoxyuridine 5'-triphosphate Chemical compound O1[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)C[C@@H]1N1C(=O)NC(=O)C=C1 AHCYMLUZIRLXAA-SHYZEUOFSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 101710163270 Nuclease Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 108010039918 Polylysine Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 208000037065 Subacute sclerosing leukoencephalitis Diseases 0.000 description 1
- 206010042297 Subacute sclerosing panencephalitis Diseases 0.000 description 1
- LSVWVFMKLGMBQM-LQABBHMDSA-N [(2S)-2-amino-3-(4-phosphonooxyphenyl)propanoyl]oxyphosphonamidous acid Chemical class NP(O)OC(=O)[C@@H](N)CC1=CC=C(OP(O)(O)=O)C=C1 LSVWVFMKLGMBQM-LQABBHMDSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000003314 affinity selection Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000003275 alpha amino acid group Chemical group 0.000 description 1
- 230000001668 ameliorated effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000692 anti-sense effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000001501 aryl fluorides Chemical class 0.000 description 1
- 238000002820 assay format Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000004057 biotinyl group Chemical group [H]N1C(=O)N([H])[C@]2([H])[C@@]([H])(SC([H])([H])[C@]12[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003593 chromogenic compound Substances 0.000 description 1
- 238000003759 clinical diagnosis Methods 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229940061607 dibasic sodium phosphate Drugs 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940087646 methanolamine Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- CMWYAOXYQATXSI-UHFFFAOYSA-N n,n-dimethylformamide;piperidine Chemical compound CN(C)C=O.C1CCNCC1 CMWYAOXYQATXSI-UHFFFAOYSA-N 0.000 description 1
- CIXHNHBHWVDBGQ-UHFFFAOYSA-N n-propan-2-ylpropan-2-amine;2h-tetrazole Chemical compound C1=NN=NN1.CC(C)NC(C)C CIXHNHBHWVDBGQ-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000011535 reaction buffer Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 108010062513 snake venom phosphodiesterase I Proteins 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/780,725 US5916750A (en) | 1997-01-08 | 1997-01-08 | Multifunctional linking reagents for synthesis of branched oligomers |
| US08/780,725 | 1997-01-08 | ||
| PCT/US1998/000445 WO1998030719A1 (en) | 1997-01-08 | 1998-01-07 | Multifunctional linking reagents for synthesis of branched oligomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2276481A1 true CA2276481A1 (en) | 1998-07-16 |
Family
ID=25120484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002276481A Abandoned CA2276481A1 (en) | 1997-01-08 | 1998-01-07 | Multifunctional linking reagents for synthesis of branched oligomers |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5916750A (https=) |
| EP (1) | EP1019534A1 (https=) |
| JP (3) | JP2000511562A (https=) |
| AU (1) | AU5912098A (https=) |
| CA (1) | CA2276481A1 (https=) |
| WO (1) | WO1998030719A1 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020022261A1 (en) * | 1995-06-29 | 2002-02-21 | Anderson Rolfe C. | Miniaturized genetic analysis systems and methods |
| JP4004230B2 (ja) * | 1998-11-06 | 2007-11-07 | 株式会社三菱化学ヤトロン | 架橋アビジン含有新規複合体、架橋アビジンを用いる分析方法、並びに分析用試薬及びキット |
| US7135284B1 (en) | 1999-02-05 | 2006-11-14 | Integrated Dna Technologies, Inc. | Primer extension methods for production of high specific activity nucleic acid probes |
| US6258593B1 (en) * | 1999-06-30 | 2001-07-10 | Agilent Technologies Inc. | Apparatus for conducting chemical or biochemical reactions on a solid surface within an enclosed chamber |
| EP1244812A1 (en) * | 1999-12-21 | 2002-10-02 | LION Bioscience AG | Branched compound for use in nucleic acid detection and analysis reactions |
| EP1111068A1 (en) * | 1999-12-21 | 2001-06-27 | LION Bioscience AG | Branched compound for use in nucleic acid detection and analysis reactions |
| GB0016813D0 (en) * | 2000-07-07 | 2000-08-30 | Lee Helen | Improved dipstick assays (4) |
| US6331632B1 (en) * | 2000-11-09 | 2001-12-18 | Beckman Coulter, Inc. | Cyanine dye phosphoramidites |
| GB0102388D0 (en) * | 2001-01-31 | 2001-03-14 | Secr Defence | Polymers |
| CA2439477C (en) * | 2001-02-27 | 2014-04-15 | Virco Bvba | Circular probe amplification (cpa) using energy-transfer primers |
| ATE432347T1 (de) * | 2002-06-24 | 2009-06-15 | Exiqon As | Methoden und systeme zur detektion und isolation von nucleinsäuresequenzen |
| EP3257949A1 (en) | 2005-06-15 | 2017-12-20 | Complete Genomics Inc. | Nucleic acid analysis by random mixtures of non-overlapping fragments |
| CA2624896C (en) | 2005-10-07 | 2017-11-07 | Callida Genomics, Inc. | Self-assembled single molecule arrays and uses thereof |
| US7960104B2 (en) * | 2005-10-07 | 2011-06-14 | Callida Genomics, Inc. | Self-assembled single molecule arrays and uses thereof |
| SG170028A1 (en) * | 2006-02-24 | 2011-04-29 | Callida Genomics Inc | High throughput genome sequencing on dna arrays |
| CN101432439B (zh) * | 2006-02-24 | 2013-07-24 | 考利达基因组股份有限公司 | Dna阵列上的高通量基因组测序 |
| US7910354B2 (en) * | 2006-10-27 | 2011-03-22 | Complete Genomics, Inc. | Efficient arrays of amplified polynucleotides |
| US20090111706A1 (en) * | 2006-11-09 | 2009-04-30 | Complete Genomics, Inc. | Selection of dna adaptor orientation by amplification |
| CA2690612C (en) | 2007-05-14 | 2016-07-05 | Historx, Inc. | Compartment segregation by pixel characterization using image data clustering |
| ES2599902T3 (es) * | 2007-06-15 | 2017-02-06 | Novartis Ag | Sistema y método de microscopio para obtener datos de muestra normalizados |
| CA2604317C (en) | 2007-08-06 | 2017-02-28 | Historx, Inc. | Methods and system for validating sample images for quantitative immunoassays |
| CA2596204C (en) * | 2007-08-07 | 2019-02-26 | Historx, Inc. | Method and system for determining an optimal dilution of a reagent |
| WO2009029810A1 (en) * | 2007-08-31 | 2009-03-05 | Historx, Inc. | Automatic exposure time selection for imaging tissue |
| WO2009132028A1 (en) * | 2008-04-21 | 2009-10-29 | Complete Genomics, Inc. | Array structures for nucleic acid detection |
| JP5551702B2 (ja) * | 2008-09-16 | 2014-07-16 | ヒストロックス，インコーポレイテッド． | バイオマーカー発現の再現性のある定量 |
| EP2539355B1 (en) * | 2010-02-26 | 2016-10-05 | Ventana Medical Systems, Inc. | In-situ hybridization with polytag probes |
| WO2011117353A1 (en) * | 2010-03-24 | 2011-09-29 | Mirrx Therapeutics A/S | Bivalent antisense oligonucleotides |
| JP2023524812A (ja) * | 2020-05-08 | 2023-06-13 | エムペグ エルエイ リミテッド ライアビリティ カンパニー | リンカー化合物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3574520A (en) * | 1966-11-02 | 1971-04-13 | Warnaco Inc | Treating cellulosic garments with a s-trimethylol triazine triol,buffered magnesium chloride,and methylol stearamide |
| US5359100A (en) * | 1987-10-15 | 1994-10-25 | Chiron Corporation | Bifunctional blocked phosphoramidites useful in making nucleic acid mutimers |
| JPH06505704A (ja) * | 1990-09-20 | 1994-06-30 | ギリアド サイエンシズ，インコーポレイテッド | 改変ヌクレオシド間結合 |
| WO1995001365A1 (en) * | 1993-07-02 | 1995-01-12 | Lynx Therapeutics, Inc. | Synthesis of branched nucleic acids |
-
1997
- 1997-01-08 US US08/780,725 patent/US5916750A/en not_active Expired - Lifetime
-
1998
- 1998-01-07 CA CA002276481A patent/CA2276481A1/en not_active Abandoned
- 1998-01-07 AU AU59120/98A patent/AU5912098A/en not_active Abandoned
- 1998-01-07 JP JP10531144A patent/JP2000511562A/ja active Pending
- 1998-01-07 EP EP98902467A patent/EP1019534A1/en not_active Withdrawn
- 1998-01-07 WO PCT/US1998/000445 patent/WO1998030719A1/en not_active Ceased
-
2004
- 2004-04-19 JP JP2004151054A patent/JP2004325457A/ja active Pending
- 2004-04-19 JP JP2004151055A patent/JP2004305216A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1019534A1 (en) | 2000-07-19 |
| AU5912098A (en) | 1998-08-03 |
| JP2004325457A (ja) | 2004-11-18 |
| JP2004305216A (ja) | 2004-11-04 |
| WO1998030719A1 (en) | 1998-07-16 |
| JP2000511562A (ja) | 2000-09-05 |
| US5916750A (en) | 1999-06-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |