Chain terminators for DNA synthesis

Chemistry: molecular biology and microbiology – Measuring or testing process involving enzymes or... – Involving nucleic acid

Reexamination Certificate

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C435S091200, C544S243000, C544S264000

Reexamination Certificate

active

06858393

ABSTRACT:
The invention relates to acyclic chain terminator nucleotide analogs. More particularly, the invention relates to phosphonomethoxyethyl nucleotide analogs and detectably labeled versions thereof, especially fluorescently labeled versions thereof. The invention further relates to the use of chain terminating phosphonomethoxyethyl nucleotide analogs in methods of synthesizing a polynucleotide, labeling a polynucleotide, determining polynucleotide sequence information, and kits therefor.

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Holy et al. (II), “Synthesis of Potential Prodrugs and Metabolites of 9-(S)-(3-hydroxy-2-phosphonylmethoxypropyl)adenine,”Coll. Czech. Chem. Comm., 52(11), 2792-2800 (Nov., 1987).*
Holy et al. (III), “Synthesis of 9-(S)-(2-phosphonylmethoxyethyl) adenine,”Coll. Czech. Chem. Comm., 52(11), 2801-2809 (Nov., 1987).*
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Starret et al., “Synthesis, Oral Bioavailability Determination, and In Vitro Evaluation of Prodrugs of the Antiviral Agent 9-[2-(Phosphonomethoxy)ethyl] adenine (PMEA),”Journal of Medicinal Chemistry, 37(12), 1857-1864 (Jun. 10, 1994).*
Wormstädt et al., “Synthesis of Acylic Nucleoside Phosphonates as Antiviral Compounds,”Journal of Heterocyclic Chemistry,37, 1187-1191 (Sep. -Oct., 2000).*
Holy et al. (IV). “Structure-Antiviral Activity Relationship in the Series of Pyrimidine and Purine N-[2-(2-Phosphonomethoxy)ethyl]Nucleotide Analogues. 1. Derivatives Substituted at the Carbon Atoms of the Base ,”Journal of Medicinal Chemistry, 42(12), 2064-2086 (Jun. 17, 1999).*
Holy et al. (V), “Synthesis of N-(2-Phosphonylmethoxyethyl) Derivatives of Heterocyclic Bases,”Coll. Czech. Chem. Comm., 54(8), 2190-2210 (Aug., 1989).*
Merta, et al. “Phosphorylation of acyclic nucleotide analogs HPMPA and PMEA in L1210 mouse lukemia cell extracts”, Neoplasma, 1990, V.37, pp. 111-120.
Martinez, et al. “Acyclic Nucleoside Triphoshate Analogs as Terminators in Biocatalytic DNA Replication”, Bioorganic & Medicinal Chemistry Letters, 1997, vol. 7, No. 23, pp. 3013-3016.
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Martinez, et al. “An allylic/acyclix adenosine nucleoside triphosphate for termination of DNA synthesis by DNA template-dependent polymerases” Nucleic Acid Research, 1999, vol. 27, No. 5, pp. 1271-1274.

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