Title:
NUCLEIC ACID SYNTHESIS METHOD USING SEGMENT-TYPE AMIDITE
Document Type and Number:
WIPO Patent Application WO/2021/141072
Kind Code:
A1
Abstract:
The purpose of the present invention is to provide a method for synthesizing an oligonucleotide by using a segment-type amidite. An oligonucleotide production method comprising at least one coupling step for coupling a nucleoside phosphoramidite with a thiol group or a hydroxyl group at the 3' or 5' of a nucleoside or a nucleotide in the presence of an activator, wherein, in the at least one coupling step, said nucleoside phosphoramidite has (a) two or more nucleoside portions or (b) at least one nucleoside portion and a linker portion, and said activator has a structure represented by formula (1) (in formula (1), X represents an organic base) or by formula (2) (in formula (2), R1 and R2 are each independently selected from the group consisting of H, straight chain or branched chain C1-7 alkyl groups and optionally substituted aromatic groups).
Inventors:
IIDA TOMOYOSHI (JP)
IWAMOTO MASAFUMI (JP)
SAKAMOTO KOTA (JP)
PAREDES EDUARDO (US)
IWAMOTO MASAFUMI (JP)
SAKAMOTO KOTA (JP)
PAREDES EDUARDO (US)
Application Number:
PCT/JP2021/000273
Publication Date:
July 15, 2021
Filing Date:
January 07, 2021
Export Citation:
Assignee:
NITTO DENKO CORP (JP)
NITTO DENKO AVECIA INC (US)
NITTO DENKO AVECIA INC (US)
International Classes:
C07H21/04
Domestic Patent References:
| WO2019212061A1 | 2019-11-07 | |||
| WO2017111137A1 | 2017-06-29 | |||
| WO2002020543A2 | 2002-03-14 | |||
| WO2019212061A1 | 2019-11-07 |
Foreign References:
| JP2017514479A | 2017-06-08 | |||
| JP2004533488A | 2004-11-04 | |||
| JP2006508081A | 2006-03-09 | |||
| JP2006512411A | 2006-04-13 | |||
| JP2017514479A | 2017-06-08 | |||
| US7501505B2 | 2009-03-10 | |||
| US6642373B2 | 2003-11-04 |
Other References:
HASSLER MATTHEW, WU YI QIAO, MALLIKARJUNA REDDY N., CHAN TAK HANG, DAMHA MASAD J.: "RNA synthesis via dimer and trimer phosphoramidite block coupling", TETRAHEDRON LETTERS, vol. 52, no. 20, 2011, pages 2575 - 2578, XP028194553, DOI: 10.1016/ j.tetlet. 2011.03.04 2
RUSSELL MARK A., LAWS ANDREW P., ATHERTON JOHN H., PAGE MICHAEL I.: "The mechanism of the phosphoramidite synthesis of polynucleotides†", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 6, no. 18, 2008, pages 3270 - 3275, XP055842214, DOI: 10.1039/ b808999j
SINHA NANDA D., FOSTER PATRICK, KUCHIMANCHI SATYA N., MIRANDA GREG, SHAIKH SAIED, MICHAUD DENNIS: "Highly Effective Non-Explosive Activators Based on Saccharin for the Synthesis of Oligonucleotides and Phosphoramidites", NUCLEOSIDES, NUCLEOTIDES & NUCLEIC ACIDS, vol. 26, no. 10-12, 2007, pages 1615 - 1618, XP055842222, DOI: 10.1080/15257770701548766
EFIMOV V A, KALINKINA A L, CHAKHMAKHCHEVA O G: "New activators for phosphoramidate synthesis of oligonucleotides", BIOORGANICHESKAYA KHIMIYA, vol. 22, no. 2, 1996, RU , pages 149 - 152, XP009537843, ISSN: 0132-3423
PAUL GAYTáN, CONTRERAS-ZAMBRANO CASANDRA, ORTIZ-ALVARADO MóNICA, MORALES-PABLOS ALFREDO, YáñEZ JORGE: "TrimerDimer: an oligonucleotide-based saturation mutagenesis approach that removes redundant and stop codons", NUCLEIC ACIDS RESEARCH, vol. 37, no. 18, 1 October 2009 (2009-10-01), GB , pages e125/1 - e125/13, XP055648565, ISSN: 0305-1048, DOI: 10.1093/nar/gkp602
CHIH-HAU CHEN; CHEN WEI-YU; CHEN YU-CHIE; LEE MING-JUAN; HUANG CHYUAN-DER; CHANDA KAUSHIK; SUN CHUNG-MING: "Convergent Solution Phase Synthesis of Chimeric Oligonucleotides by a 2+2 and 3+3 Phosphoramidite Strategy", AUSTRALIAN JOURNAL OF CHEMISTRY, vol. 63, no. 2, 2010, pages 227 - 235, XP055648558
MATTHÄUS JANCZYK; APPEL BETTINA; SPRINGSTUBBE DANILO; FRITZ HANS-JOACHIM; MÜLLER SABINE: "A new and convenient approach for the preparation of β-cyanoethyl protected trinucleotide phosphoramidites", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 10, no. 8, 2012, pages 1510 - 1513, XP055648551
"RNA synthesis via dimer and trimer phosphoramidite block coupling", TETRAHEDRON LETTERS, vol. 52, 2011, pages 2575 - 2578
RUSSELL MARK A., LAWS ANDREW P., ATHERTON JOHN H., PAGE MICHAEL I.: "The mechanism of the phosphoramidite synthesis of polynucleotides†", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 6, no. 18, 2008, pages 3270 - 3275, XP055842214, DOI: 10.1039/ b808999j
SINHA NANDA D., FOSTER PATRICK, KUCHIMANCHI SATYA N., MIRANDA GREG, SHAIKH SAIED, MICHAUD DENNIS: "Highly Effective Non-Explosive Activators Based on Saccharin for the Synthesis of Oligonucleotides and Phosphoramidites", NUCLEOSIDES, NUCLEOTIDES & NUCLEIC ACIDS, vol. 26, no. 10-12, 2007, pages 1615 - 1618, XP055842222, DOI: 10.1080/15257770701548766
EFIMOV V A, KALINKINA A L, CHAKHMAKHCHEVA O G: "New activators for phosphoramidate synthesis of oligonucleotides", BIOORGANICHESKAYA KHIMIYA, vol. 22, no. 2, 1996, RU , pages 149 - 152, XP009537843, ISSN: 0132-3423
PAUL GAYTáN, CONTRERAS-ZAMBRANO CASANDRA, ORTIZ-ALVARADO MóNICA, MORALES-PABLOS ALFREDO, YáñEZ JORGE: "TrimerDimer: an oligonucleotide-based saturation mutagenesis approach that removes redundant and stop codons", NUCLEIC ACIDS RESEARCH, vol. 37, no. 18, 1 October 2009 (2009-10-01), GB , pages e125/1 - e125/13, XP055648565, ISSN: 0305-1048, DOI: 10.1093/nar/gkp602
CHIH-HAU CHEN; CHEN WEI-YU; CHEN YU-CHIE; LEE MING-JUAN; HUANG CHYUAN-DER; CHANDA KAUSHIK; SUN CHUNG-MING: "Convergent Solution Phase Synthesis of Chimeric Oligonucleotides by a 2+2 and 3+3 Phosphoramidite Strategy", AUSTRALIAN JOURNAL OF CHEMISTRY, vol. 63, no. 2, 2010, pages 227 - 235, XP055648558
MATTHÄUS JANCZYK; APPEL BETTINA; SPRINGSTUBBE DANILO; FRITZ HANS-JOACHIM; MÜLLER SABINE: "A new and convenient approach for the preparation of β-cyanoethyl protected trinucleotide phosphoramidites", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 10, no. 8, 2012, pages 1510 - 1513, XP055648551
"RNA synthesis via dimer and trimer phosphoramidite block coupling", TETRAHEDRON LETTERS, vol. 52, 2011, pages 2575 - 2578
Attorney, Agent or Firm:
KUZUWA, Kiyoshi (JP)
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