Title:
CYTOSINE-TYPE CROSSLINKED NUCLEOSIDE AMIDITE CRYSTALS AND METHOD FOR PRODUCING SAME
Document Type and Number:
WIPO Patent Application WO/2022/124410
Kind Code:
A1
Abstract:
Provided are cytosine-type crosslinked nucleoside amidite crystals represented by a structural formula. In the formula, R2 and R2 are substitution groups and R3 is a protector group.
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Inventors:
KOHGO SATORU (JP)
Application Number:
PCT/JP2021/045679
Publication Date:
June 16, 2022
Filing Date:
December 10, 2021
Export Citation:
Assignee:
YAMASA CORP (JP)
International Classes:
C07H19/067
Domestic Patent References:
| WO2019224172A1 | 2019-11-28 | |||
| WO2020099533A1 | 2020-05-22 |
Foreign References:
| JP2004536125A | 2004-12-02 | |||
| JP2002521310A | 2002-07-16 | |||
| JPH10304889A | 1998-11-17 |
Other References:
KAORU : "Recrystallization method and precipitation method", EXPERIMENTAL CHEMISTRY COURSE (CONTINUED) 2 SEPARATION AND PURIFICATION, 25 January 1967 (1967-01-25), pages 159-178, 186 - 187, XP009509740
KOSHKIN, A.A. SINGH, S.K. NIELSEN, P. RAJWANSHI, V.K. KUMAR, R. MELDGAARD, M. OLSEN, C.E. WENGEL, J.: "LNA (Locked Nucleic Acids): Synthesis of the Adenine, Cytosine, Guanine, 5-Methylcytosine, Thymine and Uracil Bicyclonucleoside Monomers, Oligomerisation, and Unprecedented Nucleic Acid Recognition", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 54, no. 14, 2 April 1998 (1998-04-02), AMSTERDAM, NL , pages 3607 - 3630, XP004110505, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(98)00094-5
SORENSEN M D,ET AL: "alpha-L-ribo-configured locked nucleic acid (alpha-L-LNA): Synthesis and properties", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 124, no. 10, 13 March 2002 (2002-03-13), pages 2164 - 2176, XP002281373, ISSN: 0002-7863, DOI: 10.1021/ja0168763
NIELSEN POUL, ET AL.: "α-LNA (locked nucleic acid with α-D-configuration): synthesis and selective parallel recognition of RNA", CHEMISTRY-A EUROPEAN JOURNAL, vol. 8, no. 3, 2 February 2002 (2002-02-02), pages 712 - 722, XP055940870, DOI: 10.1002/1521-3765(20020201)8:3<712::AID-CHEM712>3.0.CO;2-0
T. UEMOTO ET AL.: "Direct and practical synthesis of 2'-O,4'-C-aminomethylene-bridged nucleic acid purine derivatives by transglycosylation", TETRAHEDRON, vol. 73, 2017, pages 1211 - 1218
L. TAKESHITA ET AL.: "Synthesis of Deoxypseudouridine 5'-Triphosphate Bearing the Photoremovable Protecting Group at the N1 Position Capable of Enzymatic Incorporation to DNA", J. ORG. CHEM., vol. 85, 2020, pages 1861 - 1870
M. HORIBA ET AL.: "Synthesis of scpBNA-mC, -A, and -G Monomers and Evaluation of the Binding Affinities of scpBNA-Modified Oligonucleotides toward Complementary ssRNA and ssDNA", J. ORG. CHEM., vol. 81, 2016, pages 11000 - 11008, XP055376695, DOI: 10.1021/acs.joc.6b02036
C. RIML ET AL.: "Synthesis of 5-Hydroxymethylcytidine- and 5-Hydroxymethyl-uridine-Modified RNA", SYNTHESIS, vol. 48, 2016, pages 1108 - 1116
TETRAHEDRON, vol. 54, 1998, pages 3607 - 3630
KOSHKIN, A.A. SINGH, S.K. NIELSEN, P. RAJWANSHI, V.K. KUMAR, R. MELDGAARD, M. OLSEN, C.E. WENGEL, J.: "LNA (Locked Nucleic Acids): Synthesis of the Adenine, Cytosine, Guanine, 5-Methylcytosine, Thymine and Uracil Bicyclonucleoside Monomers, Oligomerisation, and Unprecedented Nucleic Acid Recognition", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 54, no. 14, 2 April 1998 (1998-04-02), AMSTERDAM, NL , pages 3607 - 3630, XP004110505, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(98)00094-5
SORENSEN M D,ET AL: "alpha-L-ribo-configured locked nucleic acid (alpha-L-LNA): Synthesis and properties", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 124, no. 10, 13 March 2002 (2002-03-13), pages 2164 - 2176, XP002281373, ISSN: 0002-7863, DOI: 10.1021/ja0168763
NIELSEN POUL, ET AL.: "α-LNA (locked nucleic acid with α-D-configuration): synthesis and selective parallel recognition of RNA", CHEMISTRY-A EUROPEAN JOURNAL, vol. 8, no. 3, 2 February 2002 (2002-02-02), pages 712 - 722, XP055940870, DOI: 10.1002/1521-3765(20020201)8:3<712::AID-CHEM712>3.0.CO;2-0
T. UEMOTO ET AL.: "Direct and practical synthesis of 2'-O,4'-C-aminomethylene-bridged nucleic acid purine derivatives by transglycosylation", TETRAHEDRON, vol. 73, 2017, pages 1211 - 1218
L. TAKESHITA ET AL.: "Synthesis of Deoxypseudouridine 5'-Triphosphate Bearing the Photoremovable Protecting Group at the N1 Position Capable of Enzymatic Incorporation to DNA", J. ORG. CHEM., vol. 85, 2020, pages 1861 - 1870
M. HORIBA ET AL.: "Synthesis of scpBNA-mC, -A, and -G Monomers and Evaluation of the Binding Affinities of scpBNA-Modified Oligonucleotides toward Complementary ssRNA and ssDNA", J. ORG. CHEM., vol. 81, 2016, pages 11000 - 11008, XP055376695, DOI: 10.1021/acs.joc.6b02036
C. RIML ET AL.: "Synthesis of 5-Hydroxymethylcytidine- and 5-Hydroxymethyl-uridine-Modified RNA", SYNTHESIS, vol. 48, 2016, pages 1108 - 1116
TETRAHEDRON, vol. 54, 1998, pages 3607 - 3630
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AXIS PATENT INTERNATIONAL (JP)
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