ES2620131T3 - Nucleótidos marcados - Google Patents

Nucleótidos marcados Download PDF

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Publication number
ES2620131T3
ES2620131T3 ES02781434.2T ES02781434T ES2620131T3 ES 2620131 T3 ES2620131 T3 ES 2620131T3 ES 02781434 T ES02781434 T ES 02781434T ES 2620131 T3 ES2620131 T3 ES 2620131T3
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μmol
molecule
cleavable
labeled nucleotides
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Shankar Balasubramanian
Colin Barnes
Xiaohai Liu
Harold Swerdlow
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Illumina Cambridge Ltd
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Illumina Cambridge Ltd
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Priority claimed from GBGB0129012.1A external-priority patent/GB0129012D0/en
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    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/11—DNA or RNA fragments; Modified forms thereof; Non-coding nucleic acids having a biological activity
    • 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
    • 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
    • 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
    • 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
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
    • C12Q1/6869—Methods for sequencing
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q2525/00—Reactions involving modified oligonucleotides, nucleic acids, or nucleotides
    • C12Q2525/10—Modifications characterised by
    • C12Q2525/186—Modifications characterised by incorporating a non-extendable or blocking moiety
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    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q2535/00—Reactions characterised by the assay type for determining the identity of a nucleotide base or a sequence of oligonucleotides
    • C12Q2535/113—Cycle sequencing

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
  • Physics & Mathematics (AREA)
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  • Microbiology (AREA)
  • Biomedical Technology (AREA)
  • Analytical Chemistry (AREA)
  • Immunology (AREA)
  • Plant Pathology (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Saccharide Compounds (AREA)

Abstract

Una molécula de nucleótido o nucleósido, que tiene una base que se une a un marcador detectable a través de un enlazador escindible, en donde la molécula tiene una porción de azúcar ribosa o desoxirribosa que comprende un grupo protector unido a través del átomo de oxígeno 2' o 3' y el enlazador escindible y el grupo protector son escindibles bajo condiciones idénticas y en donde el enlazador puede ser escindido por exposición a radicales, metales, agentes reductores o agentes oxidantes.

Description

imagen1
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imagen8
Antraceno), 7.48 (d, J = 7.9 Hz, 1 H, H-3), 7.95 (dd, J = 8.1 Hz, J = 1.9 Hz, 1 H, H-2) 8.13 (d, J = 1.9 Hz, 1 H, H-1).+ve electro pulverización (C30H31N3O6S2): esperado 593.17; encontrado 594.3 [M+H], 616.2 [M+Na].
imagen9
20 A una solución de 25.8 mg de 1c (43.4 µmol) en 3 mL de DMF (seco) se añadió 9.9 mg N-hidroxi succinimida (86.8 µmol) y 9.7 mg de DCC (47.1 µmol).La mezcla se agitó durante 5 h en la oscuridad a temperatura ambiente y después se puso en la nevera durante toda la noche. La mezcla se filtró a través de un tapón de algodón en un nuevo matraz y a esto se añadió una solución de 865 µL de propargilamino dUTP (14.7 µmol, 17 µmol en 1 mL de H2O) y 3 mL de amortiguador borato sódico (solución 0.1 M, pH 9).La mezcla se agitó toda la noche. Después de la eliminación de los
25 disolventes el residuo se disolvió en tan poca agua como fue posible y se purificó mediante HPLC. Se usó una columna Zorbax C18 con bicarbonato de trietilamonio 0.1 M (TEAB) y acetonitrilo como amortiguadores. 31P NMR (400 MHz, D2O) : δ = -4.73 (d), -9.93 (d), 19.03 (t).-ve electro pulverización (C42H47N6O19P3S2 asumiendo 4 H+ contra iones): esperado 1096.16; encontrado 1092.9.UV en Agua: λ(max) = 555 nm A(555) = 0.885 (c = 0.036 µmol).
30 Se incorporó satisfactoriamente trifosfato (1) usando ADN polimerasa de Klenow.La reacción se realizó en las siguientes condiciones:50 mM Tris.HCl (pH 7.5), 10 mM NaCl, 2 mM DTT, 0.1 mM EDTA, 5 mM MgCl2, 2µM compuesto 3, 100 nM DNA molde (marcado previamente con P32 y T4 polinucleótido quinasa) y 10 unidades de exo-Klenow comercial (Amersham Corp., Arlington Heights, Illinois, USA).Los moldes de ADN fueron horquillas auto complementarias (5'-TACCgTCgACgTCgACgCTggCg-AgCgTgCTgCggTTTTT(C6-amino)TTACCgCAgCACgCTCgCCAgCg; Sec. con núm.
35 de ident:1).La reacción se realizó en un volumen de 100 µL a 37 ºC con puntos de tiempo tomados a 0, 1, 3, 5 y 10 min. Los productos de reacción se sometieron a electroforesis en un gel de poliacrilamida desnaturalizante (8 M de urea) al 20 % y se formaron imágenes en un PhosphorImager para Typhoon. Se observó una extensión de una sola base completa en 1 minuto que indica una incorporación eficiente de la polimerasa (gel de enlace disulfuro Figura. 4). Un segundo conjunto de carriles se muestra en el que el material se expone al DTT después de la incorporación. Un
40 cambio de banda diferente puede observarse el cual muestra la eliminación del colorante del constructo de ADN, de este modo se ha mostrado un ciclo de incorporación de la polimerasa y de escisión que usa este compuesto de disulfuro.
10

Claims (1)

  1. imagen1
ES02781434.2T 2001-12-04 2002-12-04 Nucleótidos marcados Expired - Lifetime ES2620131T3 (es)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GBGB0129012.1A GB0129012D0 (en) 2001-12-04 2001-12-04 Labelled nucleotides
GB0129012 2001-12-04
US10/227,131 US7057026B2 (en) 2001-12-04 2002-08-23 Labelled nucleotides
US227131 2002-08-23
PCT/GB2002/005474 WO2003048387A2 (en) 2001-12-04 2002-12-04 Labelled nucleotides

Publications (1)

Publication Number Publication Date
ES2620131T3 true ES2620131T3 (es) 2017-06-27

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ES02781434.2T Expired - Lifetime ES2620131T3 (es) 2001-12-04 2002-12-04 Nucleótidos marcados
ES17177650T Expired - Lifetime ES2858359T3 (es) 2001-12-04 2002-12-04 Nucleótidos marcados

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Country Status (16)

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US (4) US7057026B2 (es)
EP (4) EP1451351B1 (es)
JP (1) JP2005511058A (es)
KR (1) KR20050044668A (es)
CN (1) CN1617937A (es)
AU (1) AU2002349155A1 (es)
BR (1) BR0214683A (es)
CA (1) CA2469066A1 (es)
CY (2) CY1118765T1 (es)
DK (2) DK3266791T3 (es)
ES (2) ES2620131T3 (es)
IL (1) IL162170A0 (es)
IS (1) IS7291A (es)
PT (2) PT3266791T (es)
SI (1) SI3266791T1 (es)
WO (1) WO2003048387A2 (es)

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