WO1994000473A3 - Pentavalent synthesis of oligonucleotides containing stereospecific alkylphosphonates and arylphosphonates - Google Patents

Pentavalent synthesis of oligonucleotides containing stereospecific alkylphosphonates and arylphosphonates Download PDF

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Publication number
WO1994000473A3
WO1994000473A3 PCT/US1993/006277 US9306277W WO9400473A3 WO 1994000473 A3 WO1994000473 A3 WO 1994000473A3 US 9306277 W US9306277 W US 9306277W WO 9400473 A3 WO9400473 A3 WO 9400473A3
Authority
WO
WIPO (PCT)
Prior art keywords
methods
stereospecific
oligonucleotides
synthesis
arylphosphonates
Prior art date
Application number
PCT/US1993/006277
Other languages
French (fr)
Other versions
WO1994000473A2 (en
Inventor
Eric Wickstrom
Alexander V. Lebedev
Original Assignee
Research Corporation Technologies, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Research Corporation Technologies, Inc. filed Critical Research Corporation Technologies, Inc.
Priority to AU46611/93A priority Critical patent/AU4661193A/en
Publication of WO1994000473A2 publication Critical patent/WO1994000473A2/en
Publication of WO1994000473A3 publication Critical patent/WO1994000473A3/en

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    • 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
    • C12N15/11—DNA or RNA fragments; Modified forms thereof; Non-coding nucleic acids having a biological activity
    • C12N15/113—Non-coding nucleic acids modulating the expression of genes, e.g. antisense oligonucleotides; Antisense DNA or RNA; Triplex- forming oligonucleotides; Catalytic nucleic acids, e.g. ribozymes; Nucleic acids used in co-suppression or gene silencing
    • 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
    • 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
    • C12Q1/6813—Hybridisation assays
    • 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
    • C12Q1/6883—Nucleic acid products used in the analysis of nucleic acids, e.g. primers or probes for diseases caused by alterations of genetic material
    • C12Q1/6886—Nucleic acid products used in the analysis of nucleic acids, e.g. primers or probes for diseases caused by alterations of genetic material for cancer
    • 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
    • C12N2310/00—Structure or type of the nucleic acid
    • C12N2310/30—Chemical structure
    • C12N2310/32—Chemical structure of the sugar
    • C12N2310/321—2'-O-R Modification

Abstract

The present invention provides a method for making R stereospecific alkyl- and aryl-phosphonate linkages between nucleotides. These methods can be used for automated synthesis of oligonucleotides having sequential R stereospecific alkyl- and aryl-phosphonate linkages. The present invention is also directed to the oligonucleotides having several sequential R phosphonate linkages which were produced by the subject methods. Moreover, the present invention provides methods for using the subject oligonucleotides, including methods for regulating the biosynthesis of a DNA, an RNA or a protein and methods for detecting and isolating complementary nucleic acid targets.
PCT/US1993/006277 1992-06-30 1993-06-30 Pentavalent synthesis of oligonucleotides containing stereospecific alkylphosphonates and arylphosphonates WO1994000473A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU46611/93A AU4661193A (en) 1992-06-30 1993-06-30 Pentavalent synthesis of oligonucleotides containing stereospecific alkylphosphonates and arylphosphonates

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US90777192A 1992-06-30 1992-06-30
US907,771 1992-06-30

Publications (2)

Publication Number Publication Date
WO1994000473A2 WO1994000473A2 (en) 1994-01-06
WO1994000473A3 true WO1994000473A3 (en) 1994-02-17

Family

ID=25424615

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1993/006277 WO1994000473A2 (en) 1992-06-30 1993-06-30 Pentavalent synthesis of oligonucleotides containing stereospecific alkylphosphonates and arylphosphonates

Country Status (2)

Country Link
AU (1) AU4661193A (en)
WO (1) WO1994000473A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0653438A3 (en) * 1993-08-06 1995-10-18 Takeda Chemical Industries Ltd Oligonucleotide compounds, their production and use.
US5703223A (en) * 1994-09-02 1997-12-30 Thomas Jefferson University Solid phase synthesis of oligonucleotides with stereospecific substituted phosphonate linkages by pentavalent grignard coupling
US6486313B1 (en) 1999-02-18 2002-11-26 Isis Pharmaceuticals, Inc. Oligonucleotides having alkylphosphonate linkages and methods for their preparation
AU2002316118A1 (en) 2001-05-16 2002-11-25 Micrologix Biotech, Inc. Nucleic acid-based compounds and methods of use thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0411186A1 (en) * 1989-08-01 1991-02-06 Abbott Laboratories DNA probe assay using neutrally charged probe strands
EP0506242A1 (en) * 1991-03-06 1992-09-30 POLISH ACADEMY OF SCIENCES, Center of Molecular and Macromolecular Studies Method and compounds for solid phase synthesis of oligonucleotides and oligonucleotide analogs
US5212295A (en) * 1990-01-11 1993-05-18 Isis Pharmaceuticals Monomers for preparation of oligonucleotides having chiral phosphorus linkages

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0411186A1 (en) * 1989-08-01 1991-02-06 Abbott Laboratories DNA probe assay using neutrally charged probe strands
US5212295A (en) * 1990-01-11 1993-05-18 Isis Pharmaceuticals Monomers for preparation of oligonucleotides having chiral phosphorus linkages
EP0506242A1 (en) * 1991-03-06 1992-09-30 POLISH ACADEMY OF SCIENCES, Center of Molecular and Macromolecular Studies Method and compounds for solid phase synthesis of oligonucleotides and oligonucleotide analogs

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BRILL W K D ET AL: "Synthesis and P-diastereomeric resolution of nucleoside 3'-O-(S-alkyl) and nucleoside 3'-O-(S-aryl) methylphosphonothioates", TETRAHEDRON LETTERS., vol. 29, no. 11, 1988, OXFORD GB, pages 1227 - 1230 *
LEBEDEV A V ET AL: "Stereospecific coupling reaction for internucleotide methylphosphonothioate linkage", TETRAHEDRON LETTERS., vol. 31, no. 6, 1990, OXFORD GB, pages 855 - 858 *
STEC W.J. ET AL: "Novel route to oligo(deoxyribonucleoside phosphorothioates). Stereocontrolled synthesis of P-chiral oligo(deoxyribonucleoside phosphorothioates)", NUCLEIC ACIDS RESEARCH, vol. 19, no. 21, 1991, ARLINGTON, VIRGINIA US, pages 5883 - 5888 *

Also Published As

Publication number Publication date
AU4661193A (en) 1994-01-24
WO1994000473A2 (en) 1994-01-06

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