Title:
LONG-CHAIN DNA SYNTHESIS USING NON-NATURAL BASE
Document Type and Number:
WIPO Patent Application WO/2022/220019
Kind Code:
A1
Abstract:
The purpose of the present invention is to provide a method for synthesizing a long-chain nucleic acid (particularly DNA) with high accuracy. The present invention provides a method for synthesizing a long-chain nucleic acid, the method comprising using: (i) a nucleoside-3'-O-phosphoramidite derivative having a non-natural nucleic acid base; or (ii) a nucleoside-3'-O-phosphoramidite derivative having a non-natural nucleic acid base and a nucleoside-3'-O-phosphoramidite derivative having a natural nucleic acid base in the chemical synthesis of a nucleic acid based on the phosphoramidite method.
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Inventors:
MASAKI YOSHIAKI (JP)
Application Number:
PCT/JP2022/012843
Publication Date:
October 20, 2022
Filing Date:
March 18, 2022
Export Citation:
Assignee:
TOKYO INST TECH (JP)
International Classes:
C07H19/14; C07H21/04; C12M1/00; C12N15/10; C12N15/11
Domestic Patent References:
| WO2018155450A1 | 2018-08-30 | |||
| WO2019125974A1 | 2019-06-27 |
Foreign References:
| JP2018090562A | 2018-06-14 | |||
| JP2013520438A | 2013-06-06 |
Other References:
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INGALE SACHIN A., SEELA FRANK: "7-Deaza-2′-deoxyguanosine: Selective Nucleobase Halogenation, Positional Impact of Space-Occupying Substituents, and Stability of DNA with Parallel and Antiparallel Strand Orientation", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 81, no. 18, 16 September 2016 (2016-09-16), American Chemical Society, US, pages 8331 - 8342, XP055977933, ISSN: 0022-3263, DOI: 10.1021/acs.joc.6b01498
INGALE SACHIN A., MEI HUI, LEONARD PETER, SEELA FRANK: "Ethynyl Side Chain Hydration during Synthesis and Workup of “Clickable” Oligonucleotides: Bypassing Acetyl Group Formation by Triisopropylsilyl Protection", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 78, no. 22, 15 November 2013 (2013-11-15), American Chemical Society, US, pages 11271 - 11282, XP055977937, ISSN: 0022-3263, DOI: 10.1021/jo401780u
SEELA FRANK, XU KUIYING: "DNA with stable fluorinated dA and dG substitutes: syntheses, base pairing and 19F-NMR spectra of 7-fluoro-7-deaza-2′-deoxyadenosine and 7-fluoro-7-deaza-2′-deoxyguanosine", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 6, no. 19, 1 January 2008 (2008-01-01), pages 3552 - 3560, XP055774483, ISSN: 1477-0520, DOI: 10.1039/b806145a
F.SEELA ET AL.: "Alternating d(G-C)3 and d(C-G)3 Hexanucleotides Containing 7-Deaza-2'-Deoxyguanosine or 8-Aza-7-deaza-2'-deoxyguanosine in Place of dG.", NUCLEIC ACIDS RESEARCH, vol. 17., no. 03., 1 January 1989 (1989-01-01), Oxford University Press, GB, pages 901 - 910., XP002078861, ISSN: 0305-1048
HU TIANNAN; SUTER SCOTT R.; MUMBLEAU MADELINE M.; BEAL PETER A.: "TLR8 activation and inhibition by guanosine analogs in RNA: Importance of functional groups and chain length", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 26, no. 1, 11 November 2017 (2017-11-11), ELSEVIER, AMSTERDAM, NL, pages 77 - 83, XP085307307, ISSN: 0968-0896, DOI: 10.1016/j.bmc.2017.11.020
INGALE SACHIN A., SEELA FRANK: "7-Deaza-2′-deoxyguanosine: Selective Nucleobase Halogenation, Positional Impact of Space-Occupying Substituents, and Stability of DNA with Parallel and Antiparallel Strand Orientation", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 81, no. 18, 16 September 2016 (2016-09-16), American Chemical Society, US, pages 8331 - 8342, XP055977933, ISSN: 0022-3263, DOI: 10.1021/acs.joc.6b01498
INGALE SACHIN A., MEI HUI, LEONARD PETER, SEELA FRANK: "Ethynyl Side Chain Hydration during Synthesis and Workup of “Clickable” Oligonucleotides: Bypassing Acetyl Group Formation by Triisopropylsilyl Protection", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 78, no. 22, 15 November 2013 (2013-11-15), American Chemical Society, US, pages 11271 - 11282, XP055977937, ISSN: 0022-3263, DOI: 10.1021/jo401780u
SEELA FRANK, XU KUIYING: "DNA with stable fluorinated dA and dG substitutes: syntheses, base pairing and 19F-NMR spectra of 7-fluoro-7-deaza-2′-deoxyadenosine and 7-fluoro-7-deaza-2′-deoxyguanosine", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 6, no. 19, 1 January 2008 (2008-01-01), pages 3552 - 3560, XP055774483, ISSN: 1477-0520, DOI: 10.1039/b806145a
F.SEELA ET AL.: "Alternating d(G-C)3 and d(C-G)3 Hexanucleotides Containing 7-Deaza-2'-Deoxyguanosine or 8-Aza-7-deaza-2'-deoxyguanosine in Place of dG.", NUCLEIC ACIDS RESEARCH, vol. 17., no. 03., 1 January 1989 (1989-01-01), Oxford University Press, GB, pages 901 - 910., XP002078861, ISSN: 0305-1048
Attorney, Agent or Firm:
AOKI, Atsushi et al. (JP)
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