Nucleoside analogues
First Claim
Patent Images
1. A nucleoside analogue of the formula:
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where Z is O, S, Se, SO NR9 or CH2, R1, R2, R3 and R4 are the same or different and each is H, OH, F, NH2, N3, O-hydrocarbyl or a reporter moiety, R5 is OH or mono-, di- or tri-phosphate or -thiophosphate or corresponding boranophosphate, or one of R2 and R5 is a phosphoramidite or other group for incorporation in a polynucleotide chain, and M is;
where X1, X2 and X3 are the same or different and each is C or N, when X3 is N, there is no R7 group, R6 and R7 are the same or different and each is H, NO2, CO, COR8, OR8, CN, O, CON(R8)2, COOR8, SO2R8, SO3R8, SR8, NHCHO, (CH2)nN(R8)2, halogen, or a reporter moiety, each of R8 and R9 is H or hydrocarbyl or a reporter moiety, and n is 0, 1, 2, 3 or 4, provided that when R5 is not triphosphate, then the nucleoside analogue comprises a reporter moiety and provided that, when M is benzimidazolyl and a reporter moiety is absent, the M has the structure;
and R6 is not H, and further provided that when M is;
then R5 is not OH.
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Accused Products
Abstract
Nucleoside analogues in which a group M replaces the natural base where M is (1) or (2) or (3), where each of X1, X2 and X3 are C or N, each of R6 and R7 is the same or different and each is H, NO2, CO, COR8, OR8, CN, O, CON(R8)2, COOR8, SO2R8, SO3R8, SR8, NHCHO, (CH2)n(R8)2, halogen, or a reporter moiety, each of R8 and R9 is H or hydrocarbyl or a reporter moiety, and n is 0-4. The analogues are substrates for polymerase and terminal transferase enzymes.
151 Citations
12 Claims
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1. A nucleoside analogue of the formula:
-
where Z is O, S, Se, SO NR9 or CH2, R1, R2, R3 and R4 are the same or different and each is H, OH, F, NH2, N3, O-hydrocarbyl or a reporter moiety, R5 is OH or mono-, di- or tri-phosphate or -thiophosphate or corresponding boranophosphate, or one of R2 and R5 is a phosphoramidite or other group for incorporation in a polynucleotide chain, and M is;
where X1, X2 and X3 are the same or different and each is C or N, when X3 is N, there is no R7 group, R6 and R7 are the same or different and each is H, NO2, CO, COR8, OR8, CN, O, CON(R8)2, COOR8, SO2R8, SO3R8, SR8, NHCHO, (CH2)nN(R8)2, halogen, or a reporter moiety, each of R8 and R9 is H or hydrocarbyl or a reporter moiety, and n is 0, 1, 2, 3 or 4, provided that when R5 is not triphosphate, then the nucleoside analogue comprises a reporter moiety and provided that, when M is benzimidazolyl and a reporter moiety is absent, the M has the structure;
and R6 is not H, and further provided that when M is;
then R5 is not OH. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10)
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11. A method of detecting a nucleic acid which contains a residue of a nucleoside analogue of the formula:
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where Z is O, S, Se, SO, NR9 or CH2, R1, R2, R3 and R4 are the same or different and each is H, OH, F, NH2, N3, O-hydrocarbyl or a reporter moiety, R5 is OH or mono-, di- or tri-phosphate or -thiophosphate or corresponding boranophosphate, or one of R2 and R5 is a phosphoramidite or other group for incorporation in a polynucleotide chain, and M is;
where X1, X2 and X3 are the same or different and each is C or N, when X3 is N, there is no R7 group, R6 and R7 are the same or different and each is H, NO2, CO, COR8, OR8, CN, O, CON(R8)2, COOR8, SO2R8, SO3R8, SR8, NHCHO, (CH2)nN(R8)2, halogen, or a reporter moiety, each of R8 and R9 is H or hydrocarbyl or a reporter moiety, and n is 0, 1, 2, 3 or 4, which method comprises using for detection an antibody which binds to M.
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12. [1-(2′
- -deoxy-β
-D-ribofuranosyl)-pyrrole-3,4-dicarboxamide]5′
-triphosphate.
- -deoxy-β
Specification
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- Resources
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Current AssigneeMedical Research Council (Government of United Kingdom)
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Original AssigneeAmersham Pharmacia Biotech UK Ltd. (Danaher Corporation)
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InventorsSmith, Clifford, Loakes, David, Simmonds, Adrian, Hamilton, Alan, Brown, Daniel
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Primary Examiner(s)Riley, Jezia
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Application NumberUS09/101,978Time in Patent Office757 DaysField of Search435/6, 435/91.1, 435/91.2, 536/22.1, 536/23.1, 536/24.3, 536/24.33, 536/25.32, 514/394, 514/395US Class Current514/394CPC Class CodesC07H 19/044 Pyrrole radicalsC07H 19/052 Imidazole radicalsC07H 19/056 Triazole or tetrazole radicalsC07H 21/00 Compounds containing two or...
