WO1994000472A3 - Trivalent synthesis of oligonucleotides containing stereospecific alkylphosphonates and arylphosphonates - Google Patents

Trivalent synthesis of oligonucleotides containing stereospecific alkylphosphonates and arylphosphonates Download PDF

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Publication number
WO1994000472A3
WO1994000472A3 PCT/US1993/006251 US9306251W WO9400472A3 WO 1994000472 A3 WO1994000472 A3 WO 1994000472A3 US 9306251 W US9306251 W US 9306251W WO 9400472 A3 WO9400472 A3 WO 9400472A3
Authority
WO
WIPO (PCT)
Prior art keywords
methods
stereospecific
oligonucleotides
synthesis
arylphosphonates
Prior art date
Application number
PCT/US1993/006251
Other languages
French (fr)
Other versions
WO1994000472A2 (en
Inventor
Eric Wickstrom
Jason P Rife
Original Assignee
Res Corp 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 Res Corp Technologies Inc filed Critical Res Corp Technologies Inc
Priority to AU46598/93A priority Critical patent/AU4659893A/en
Publication of WO1994000472A2 publication Critical patent/WO1994000472A2/en
Publication of WO1994000472A3 publication Critical patent/WO1994000472A3/en

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Classifications

    • 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

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Organic Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Physics & Mathematics (AREA)
  • Biophysics (AREA)
  • Plant Pathology (AREA)
  • Microbiology (AREA)
  • Saccharide Compounds (AREA)

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/US1993/006251 1992-06-30 1993-06-30 Trivalent synthesis of oligonucleotides containing stereospecific alkylphosphonates and arylphosphonates WO1994000472A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU46598/93A AU4659893A (en) 1992-06-30 1993-06-30 Trivalent synthesis of oligonucleotides containing stereospecific alkylphosphonates and arylphosphonates

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US90776892A 1992-06-30 1992-06-30
US907,768 1992-06-30

Publications (2)

Publication Number Publication Date
WO1994000472A2 WO1994000472A2 (en) 1994-01-06
WO1994000472A3 true WO1994000472A3 (en) 1994-02-17

Family

ID=25424612

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1993/006251 WO1994000472A2 (en) 1992-06-30 1993-06-30 Trivalent synthesis of oligonucleotides containing stereospecific alkylphosphonates and arylphosphonates

Country Status (2)

Country Link
AU (1) AU4659893A (en)
WO (1) WO1994000472A2 (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2129565A1 (en) * 1993-08-06 1995-02-07 Hiroshi Tanimura 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
US5789576A (en) * 1994-12-09 1998-08-04 Genta Incorporated Methylphosphonate dimer synthesis
US6177614B1 (en) * 1995-03-16 2001-01-23 Cold Spring Harbor Laboratory Control of floral induction in plants and uses therefor
US5821354A (en) * 1996-11-26 1998-10-13 Angiogene Inc. Radiolabeled DNA oligonucleotide and method of preparation
US6486313B1 (en) * 1999-02-18 2002-11-26 Isis Pharmaceuticals, Inc. Oligonucleotides having alkylphosphonate linkages and methods for their preparation
US7259253B2 (en) * 1999-05-14 2007-08-21 Quark Biotech, Inc. Genes associated with mechanical stress, expression products therefrom, and uses thereof
JP2004508379A (en) * 2000-09-07 2004-03-18 アベシア・バイオテクノロジー・インコーポレーテッド Synthons for oligonucleotide synthesis
KR20040074594A (en) 2001-05-16 2004-08-25 마이크로로직스 바이오테크, 인코포레이티드 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 (4)

* Cited by examiner, † Cited by third party
Title
BRILL W K D ET AL: "Oxidative and nonoxidative formation of internucleotide linkages", TETRAHEDRON LETTERS., vol. 30, no. 48, 1989, OXFORD GB, pages 6621 - 6624, XP002915795, DOI: doi:10.1016/S0040-4039(00)70634-4 *
STAWINSKI J ET AL: "Nucleoside H-phosphonates. 12. Synthesis of nucleoside 3'-(hydrogen phosphonothioate) monoesters via phosphinate intermediates", JOURNAL OF ORGANIC CHEMISTRY, vol. 55, 1990, EASTON US, pages 3503 - 3506, XP002075156, DOI: doi:10.1021/jo00298a023 *
STAWINSKI J ET AL: "Nucleoside H-phosphonates. X. Studies on nucleoside hydrogen phosphonothioate diester synthesis", TETRAHEDRON LETTERS., vol. 30, no. 16, 1989, OXFORD GB, pages 2157 - 2160 *
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
AU4659893A (en) 1994-01-24
WO1994000472A2 (en) 1994-01-06

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