Title:
MONOMER FOR SYNTHESIS OF RNA, METHOD FOR PRODUCING SAME, AND METHOD FOR PRODUCING RNA
Document Type and Number:
WIPO Patent Application WO/2014/017615
Kind Code:
A1
Abstract:
The purpose of the present invention is to provide: a monomer for the synthesis of RNA, which can be produced with high efficiency and consequently enables the remarkable reduction in the cost for the production of RNA; a method for producing a monomer for the synthesis of RNA in fewer steps with high efficiency; and a method which can synthesize RNA with high efficiency even when a monomer for the synthesis of the RNA is used in an almost stoichiometric amount. The monomer for the synthesis of RNA according to the present invention is characterized by being represented by formula (I) or (I'). [In the formulae, R1 represents a protective group for a hydroxy group; and R2 represents an alkyl group or the like.]
Inventors:
KATAOKA MASANORI (JP)
Application Number:
PCT/JP2013/070247
Publication Date:
January 30, 2014
Filing Date:
July 25, 2013
Export Citation:
Assignee:
UNIV KOCHI (JP)
International Classes:
C07H19/10; C07H19/20; C07H21/02
Domestic Patent References:
| WO2011030353A2 | 2011-03-17 | |||
| WO2002079215A1 | 2002-10-10 |
Foreign References:
| JP2011512390A | 2011-04-21 | |||
| JP2006077013A | 2006-03-23 | |||
| JP2011521930A | 2011-07-28 |
Other References:
E. ROZNERS ET AL.: "Synthesis of oligoribonucleotides by the H-phosphonate approach using base-labile 2'-O-protecting groups.", V. RECENT PROGRESS IN DEVELOPMENT OF THE METHOD, NUCLEOSIDES & NUCLEOTIDES, vol. 11, no. 9, 1992, pages 1579 - 1593, XP008176005
E. ROZNERS ET AL.: "Synthesis of RNA fragments using the H-phosphonate method and 2'-(2- chlorobenzoyl) protection", NUCLEOSIDES & NUCLEOTIDES, vol. 14, no. 3-5, 1995, pages 855 - 857, XP008175985
E. ROZNERS ET AL.: "Evaluation of 2'-hydroxyl protection in RNA-synthesis using the H- phosphonate approach", NUCLEIC ACIDS RESEARCH, vol. 22, no. 1, 1994, pages 94 - 99, XP002919964
E. ROZNERS ET AL.: "Solid-phase synthesis of oligoribonucleotides by the H-phosphonate method using 2'-O-benzoyl protective group", BIOORGANICHESKAYA KHIMIYA, vol. 14, no. 11, 1988, pages 1580 - 1582, XP008175978
E. ROZNERS ET AL.: "Synthesis of oligoribonucleotides by the H-phosphonate approach using base-labile 2'-O-protecting groups.", IV. A NEW APPROACH TO SOLVE THE PROBLEM OF MODIFICATION AND DEGRADATION OF OLIGORIBONUCLEOTIDES, vol. 18, no. 2, 1992, pages 137 - 144, XP008176004
PER J. GAREGG ET AL.: "Nucleoside H-Phosphonates. IV. Automated Solid Phase Synthesis of Oligoribonucleotides by the Hydrogenphosphonate Approach", TETRAHEDRON LETTERS, vol. 27, no. 34, 1986, pages 4055 - 4058, XP002082972
NEILANDS, OJARS ET AL.: "Synthesis of Novel Tetrathiafulvalene System Containing Redox- Active Ribonucleoside and Oligoribonucleotide", ORGANIC LETTERS, vol. 1, no. 13, 1999, pages 2065 - 2067, XP055183187
"PROTECTION FOR THE HYDROXYL GROUP, INCLUDING 1,2- AND 1,3-DIOLS", PROTECTIVE GROUPS IN ORGANIC SYNTHESIS, 1991, pages 10 - 14, XP008175998
E. ROZNERS ET AL.: "Building blocks for synthesis of oligoarabinonucleotides: preparation of arabinonucleoside H-phosphonates from protected ribonucleosides", NUCLEOSIDES & NUCLEOTIDES, vol. 14, no. 9-10, 1995, pages 2009 - 2025, XP008175987
E. ROZNERS ET AL.: "Synthesis of oligoarabinonucleotides using H-phosphonates", NUCLEOSIDES & NUCLEOTIDES, vol. 14, no. 3-5, 1995, pages 851 - 853, XP008175984
XIAOHU ZHAN ET AL.: "High Yield Protection of Purine Ribonucleosides for H-Phosphonate RNA Synthesis", TETRAHEDRON LETTERS, vol. 38, no. 41, 1997, pages 7135 - 7138, XP027242258
SHOICHIRO OZAKI ET AL.: "Enzyme aided regio- selective acylation and deacylation of nucleosides", NUCLEIC ACIDS SYMPOSIUM SERIES, 1993, pages 53 - 54, XP008176002
SHOICHIRO OZAKI ET AL.: "Enzyme Aided Regioselective Acylation of Nucleosides", NUCLEOSIDES & NUCLEOTIDES, vol. 14, no. 3-5, 1995, pages 401 - 404, XP008175986
FRANCISCO MORIS ET AL.: "A useful and versatile procedure for the acylation of nucleosides through an enzymic reaction", JOURNAL OF ORGANIC CHEMISTRY, vol. 58, no. 3, 1993, pages 653 - 660, XP009054627
See also references of EP 2878604A4
XIAOHU ZHANG ET AL., TETRAHEDRON LETTERS, vol. 38, no. 41, 1997, pages 7135 - 7138
E. ROZNERS ET AL.: "Synthesis of RNA fragments using the H-phosphonate method and 2'-(2- chlorobenzoyl) protection", NUCLEOSIDES & NUCLEOTIDES, vol. 14, no. 3-5, 1995, pages 855 - 857, XP008175985
E. ROZNERS ET AL.: "Evaluation of 2'-hydroxyl protection in RNA-synthesis using the H- phosphonate approach", NUCLEIC ACIDS RESEARCH, vol. 22, no. 1, 1994, pages 94 - 99, XP002919964
E. ROZNERS ET AL.: "Solid-phase synthesis of oligoribonucleotides by the H-phosphonate method using 2'-O-benzoyl protective group", BIOORGANICHESKAYA KHIMIYA, vol. 14, no. 11, 1988, pages 1580 - 1582, XP008175978
E. ROZNERS ET AL.: "Synthesis of oligoribonucleotides by the H-phosphonate approach using base-labile 2'-O-protecting groups.", IV. A NEW APPROACH TO SOLVE THE PROBLEM OF MODIFICATION AND DEGRADATION OF OLIGORIBONUCLEOTIDES, vol. 18, no. 2, 1992, pages 137 - 144, XP008176004
PER J. GAREGG ET AL.: "Nucleoside H-Phosphonates. IV. Automated Solid Phase Synthesis of Oligoribonucleotides by the Hydrogenphosphonate Approach", TETRAHEDRON LETTERS, vol. 27, no. 34, 1986, pages 4055 - 4058, XP002082972
NEILANDS, OJARS ET AL.: "Synthesis of Novel Tetrathiafulvalene System Containing Redox- Active Ribonucleoside and Oligoribonucleotide", ORGANIC LETTERS, vol. 1, no. 13, 1999, pages 2065 - 2067, XP055183187
"PROTECTION FOR THE HYDROXYL GROUP, INCLUDING 1,2- AND 1,3-DIOLS", PROTECTIVE GROUPS IN ORGANIC SYNTHESIS, 1991, pages 10 - 14, XP008175998
E. ROZNERS ET AL.: "Building blocks for synthesis of oligoarabinonucleotides: preparation of arabinonucleoside H-phosphonates from protected ribonucleosides", NUCLEOSIDES & NUCLEOTIDES, vol. 14, no. 9-10, 1995, pages 2009 - 2025, XP008175987
E. ROZNERS ET AL.: "Synthesis of oligoarabinonucleotides using H-phosphonates", NUCLEOSIDES & NUCLEOTIDES, vol. 14, no. 3-5, 1995, pages 851 - 853, XP008175984
XIAOHU ZHAN ET AL.: "High Yield Protection of Purine Ribonucleosides for H-Phosphonate RNA Synthesis", TETRAHEDRON LETTERS, vol. 38, no. 41, 1997, pages 7135 - 7138, XP027242258
SHOICHIRO OZAKI ET AL.: "Enzyme aided regio- selective acylation and deacylation of nucleosides", NUCLEIC ACIDS SYMPOSIUM SERIES, 1993, pages 53 - 54, XP008176002
SHOICHIRO OZAKI ET AL.: "Enzyme Aided Regioselective Acylation of Nucleosides", NUCLEOSIDES & NUCLEOTIDES, vol. 14, no. 3-5, 1995, pages 401 - 404, XP008175986
FRANCISCO MORIS ET AL.: "A useful and versatile procedure for the acylation of nucleosides through an enzymic reaction", JOURNAL OF ORGANIC CHEMISTRY, vol. 58, no. 3, 1993, pages 653 - 660, XP009054627
See also references of EP 2878604A4
XIAOHU ZHANG ET AL., TETRAHEDRON LETTERS, vol. 38, no. 41, 1997, pages 7135 - 7138
Attorney, Agent or Firm:
UEKI, Kyuichi et al. (JP)
Hisakazu Ueki (JP)
Hisakazu Ueki (JP)
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