DK2970356T3 - Modificerede nukleosider eller nukleotider - Google Patents

Modificerede nukleosider eller nukleotider Download PDF

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Publication number
DK2970356T3
DK2970356T3 DK13711333.8T DK13711333T DK2970356T3 DK 2970356 T3 DK2970356 T3 DK 2970356T3 DK 13711333 T DK13711333 T DK 13711333T DK 2970356 T3 DK2970356 T3 DK 2970356T3
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Denmark
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hydrogen
modified nucleotide
nucleotide
nucleoside
optionally substituted
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DK13711333.8T
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English (en)
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Xiaohai Liu
Xiaolin Wu
Geoffrey Paul Smith
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Illumina Cambridge Ltd
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    • 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
    • C07H19/073—Pyrimidine radicals with 2-deoxyribosyl as the saccharide radical
    • 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
    • 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
    • C07H19/14—Pyrrolo-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
    • C07H19/16—Purine radicals
    • C07H19/173—Purine radicals with 2-deoxyribosyl as the saccharide radical
    • 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
    • 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
    • C12Q1/6876—Nucleic acid products used in the analysis of nucleic acids, e.g. primers or probes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Claims (15)

1. Et modificeret nukleotid eller nukleosid molekyle omfattende en purin eller pyrimidin base og en ribose eller deoxyribose sukker del med en flytbar 3'-hydroxy beskyttelsesgruppe dannende en struktur -O-C(R)2N3 kovalent fæstnet til 3'-carbon atomet, hvori R er valgt fra gruppen bestående af hydrogen, -C (R1) m (R2) n, C(=O)OR3, -C(=O)NR4R5, -C (R6) 20 (CH2) pNR7R8 og -C(R9)2O-Ph-C (=0) NR10Rn ; hvert R1 og R2 er uafhængigt udvalgt fra hydrogen eller halogen; R3 er udvalgt fra hydrogen eller valgfri erstattet alkyl; hvert R4 og R5 er uafhængigt udvalgt fra hydrogen, valgfri erstattet alkyl, valgfri erstattet aryl, valgfri erstattet heteroaryl, eller valgfri erstattet aralkyl; hvert R6 og R9 er udvalgt fra hydrogen, valgfri erstattet alkyl eller halogen; hvert R7, R8, R10 og R11 er uafhængigt udvalgt fra hydrogen, valgfri erstattet alkyl, valgfri erstattet aryl, valgfrit erstattet heteroaryl eller valgfri erstattet aralkyl; m er et helt tal på 0 til 3; n er et helt tal på 0 til 3; forudsat at totalen af m + n er lig 3; og p er et helt tal på 0 til 6; forudsat at R1 og R2 ikke begge kan være halogen; og at mindst et R ikke er hydrogen.
2. Det modificerede nukleotid eller nukleosid molekyle ifølge patentkrav 1, hvori et af R er hydrogen og det andet R er -C(R1)m(R2)n og hvori -C(R1)m(R2)n er udvalgt fra -CHF2, -CH2F, -CHCI2 eller -CH2C1.
3. Det modificerede nukleotid eller nukleosid molekyle ifølge patentkrav 1, hvori et af R er hydrogen og det andet R er -C(=O)OR3, fortrinsvis R3 er hydrogen.
4. Det modificerede nukleotid eller nuclesid molekyle ifølge patentkrav 1, hvori et af R er hydrogen og det andet R er -C(=O)NR4R5, hvori hvert af R4 og R5 er udvalgt fra hydrogen eller Ci-6 alkyl.
5. Det modificerede nukleotid eller nukleosid molekyle ifølge patentkrav 1, hvori et af R er hydrogen og det andet R er -C (R6) 2O (CH2) PNR7R8, fortrinsvis R6 er hydrogen og hvert R7 og R8 er hydrogen.
6. Det modificerede nukleotid eller nukleosid molekyle ifølge patentkrav 1, hvori et af R er hydrogen og det andet R er -C (R9) 20-Ph-C (=0) NR10R1:L, fortrinsvis hvert R9 og R10 er hydrogen og R11 er udvalgt fra hydrogen eller en amino substitueret alkyl.
7. Det modificerede nukleotid eller nukleosid molekyle ifølge et af patentkravene 1 til 5, hvori 3'-hydroxy beskyttelsesgruppen er fjernet i en afbeskyttende reaktion med en phosphin.
8. Det modificerede nukleotid eller nukleosid molekyle ifølge patentkrav 7, hvori phosphinen er tris(hydroxymethyl)phosphin (THP).
9. Det modificerede nukleotid eller nukleosid molekyle ifølge et af patentkravene 1 til 8, hvori nævnte base er forbundet med en påviselig label via en spaltbar forbindelse eller en ikke-spaltbar forbindelse, og hvori den påviselige label er en fluorophor.
10. Det modificerede nukleotid eller nukleosid molekyle ifølge et af patentkravene 1 til 8, hvori nævnte 3'-hydroxy beskyttelses-gruppe er forbundet til en påviselig label via en spaltbar forbindelse eller en ikke-spaltbar forbindelse og hvori den påviselige label er en fluorophor.
11. En metode til at fremstille en polynucleotide komplementær til målet en enkeltstrenget polynucleotide i en sekvenserings reaktion, omfattende indarbejdelse af en modificerede nukleotid molekyle ifølge et af patentkravene 1 til 10 til den voksende komplementære polynucleotide, hvori indarbejdelsen af den modi-ficerede nukleotid forhindrer indførelsen af nogen efterfølgende nukleotid i den voksende komplementære polynucleotide.
12. Metoden ifølge patentkrav 11, hvori indførelsen af den modificerede nukleotid molekyle er opnået ved en terminal transferase, en terminal polymerase eller en revers transcriptase.
13. En metode til bestemmelse af sekvensen af målet en enkelt-strenget polynucleotide, omfattende kontrol af sekventiel indarbejdelse af komplementære nukleotider, hvori mindst en komplementær indarbejdet nukleotid er en modificeret nukleotid molekyle ifølge patentkrav 9 eller 10; og bestemmelse af identiteten af den modificerede nukleotid molekyle.
14. Metoden ifølge patentkrav 13, hvori identiteten af den modificerede nukleotid er fastslået ved at påvise den påviselige label forbundet til basen.
15. Et sæt omfattende flere modificerede nukleotid eller nukleosid molekyler ifølge et af patentkravene 1 til 10 og emballeringsmateriale dertil.
DK13711333.8T 2013-03-15 2013-03-15 Modificerede nukleosider eller nukleotider DK2970356T3 (da)

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PCT/EP2013/055466 WO2014139596A1 (en) 2013-03-15 2013-03-15 Modified nucleosides or nucleotides

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US (3) US9593373B2 (da)
EP (2) EP3388442A1 (da)
JP (1) JP6333297B2 (da)
KR (2) KR101874680B1 (da)
CN (2) CN108864232B (da)
AU (1) AU2013382358B2 (da)
BR (1) BR112015022448B1 (da)
CA (1) CA2903095C (da)
DK (1) DK2970356T3 (da)
ES (1) ES2685549T3 (da)
HK (1) HK1220463A1 (da)
WO (1) WO2014139596A1 (da)

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