Title:
COMPOUND PRODUCTION METHOD
Document Type and Number:
WIPO Patent Application WO/2024/071320
Kind Code:
A1
Abstract:
The present invention provides a method with which it is possible to simply produce a peptide including an aromatic six-membered ring in the scaffold. The present invention pertains to a production method for a compound represented by formula (I), said production method including reacting a compound represented by formula (1) with an amino acid or amino acid derivative or peptide which binds to a solid support and has a free amino group, or with a solid support having a free amino group, to obtain a compound represented by formula (2), wherein a compound obtained by deprotecting the PG of the compound represented by formula (2) is cleaved from the solid support and a cyclization reaction is performed after at least one amino acid condensation reaction is optionally performed.
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Inventors:
SUGA HIROAKI (JP)
GOTO YUKI (JP)
VINOGRADOV ALEXANDER (JP)
ZHANG YUE (JP)
CHANG JUN SHI (JP)
GOTO YUKI (JP)
VINOGRADOV ALEXANDER (JP)
ZHANG YUE (JP)
CHANG JUN SHI (JP)
Application Number:
PCT/JP2023/035472
Publication Date:
April 04, 2024
Filing Date:
September 28, 2023
Export Citation:
Assignee:
UNIV TOKYO (JP)
International Classes:
C07K1/04; C07K1/06
Domestic Patent References:
| WO2020067550A1 | 2020-04-02 |
Other References:
ALEXANDER A. VINOGRADOV: "Introduction to Thiopeptides: Biological Activity, Biosynthesis, and Strategies for Functional Reprogramming", CELL CHEMICAL BIOLOGY, ELSEVIER, AMSTERDAM, NL, vol. 27, no. 8, 1 August 2020 (2020-08-01), AMSTERDAM, NL , pages 1032 - 1051, XP093155949, ISSN: 2451-9456, DOI: 10.1016/j.chembiol.2020.07.003
K. PHILIP WOJTAS; MATTHIAS RIEDRICH; JIN‐YONG LU; PHILIPP WINTER; THOMAS WINKLER; SOPHIA WALTER; HANS‐DIETER ARNDT: "Total Synthesis of Nosiheptide", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, HOBOKEN, USA, vol. 55, no. 33, 27 June 2016 (2016-06-27), Hoboken, USA, pages 9772 - 9776, XP072090331, ISSN: 1433-7851, DOI: 10.1002/anie.201603140
TOMONORI MORI; SHUHEI HIGASHIBAYASHI; TAIJI GOTO; MITSUNORI KOHNO; YUKIKO SATOUCHI; KAZUYUKI SHINKO; KENGO SUZUKI; SHUNYA SUZUKI; : "Total Synthesis of Siomycin A: Completion of the Total Synthesis", CHEMISTRY - AN ASIAN JOURNAL, WILEY-VCH, HOBOKEN, USA, vol. 3, no. 6, 7 May 2008 (2008-05-07), Hoboken, USA, pages 1013 - 1025, XP072416746, ISSN: 1861-4728, DOI: 10.1002/asia.200800033
HEE-JONG HWANG: "Diversity-oriented routes to thiopeptide antibiotics: total synthesis and biological evaluation of micrococcin P2", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 20, no. 9, 2 March 2022 (2022-03-02), pages 1893 - 1899, XP093155952, ISSN: 1477-0520, DOI: 10.1039/D1OB02145A
WALTER J. WEVER: "Identification of Pyridine Synthase Recognition Sequences Allows a Modular Solid-Phase Route to Thiopeptide Variants", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 138, no. 41, 19 October 2016 (2016-10-19), pages 13461 - 13464, XP093155953, ISSN: 0002-7863, DOI: 10.1021/jacs.6b05389
ACOSTA GERARDO A.; ROYO MIRIAM; DE LA TORRE BEATRIZ G.; ALBERICIO FERNANDO: "Facile solid-phase synthesis of head-side chain cyclothiodepsipeptides through a cyclative cleavage from MeDbz-resin", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 58, no. 28, 14 June 2017 (2017-06-14), Amsterdam , NL , pages 2788 - 2791, XP085081569, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2017.06.008
K. PHILIP WOJTAS; MATTHIAS RIEDRICH; JIN‐YONG LU; PHILIPP WINTER; THOMAS WINKLER; SOPHIA WALTER; HANS‐DIETER ARNDT: "Total Synthesis of Nosiheptide", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, HOBOKEN, USA, vol. 55, no. 33, 27 June 2016 (2016-06-27), Hoboken, USA, pages 9772 - 9776, XP072090331, ISSN: 1433-7851, DOI: 10.1002/anie.201603140
TOMONORI MORI; SHUHEI HIGASHIBAYASHI; TAIJI GOTO; MITSUNORI KOHNO; YUKIKO SATOUCHI; KAZUYUKI SHINKO; KENGO SUZUKI; SHUNYA SUZUKI; : "Total Synthesis of Siomycin A: Completion of the Total Synthesis", CHEMISTRY - AN ASIAN JOURNAL, WILEY-VCH, HOBOKEN, USA, vol. 3, no. 6, 7 May 2008 (2008-05-07), Hoboken, USA, pages 1013 - 1025, XP072416746, ISSN: 1861-4728, DOI: 10.1002/asia.200800033
HEE-JONG HWANG: "Diversity-oriented routes to thiopeptide antibiotics: total synthesis and biological evaluation of micrococcin P2", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 20, no. 9, 2 March 2022 (2022-03-02), pages 1893 - 1899, XP093155952, ISSN: 1477-0520, DOI: 10.1039/D1OB02145A
WALTER J. WEVER: "Identification of Pyridine Synthase Recognition Sequences Allows a Modular Solid-Phase Route to Thiopeptide Variants", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 138, no. 41, 19 October 2016 (2016-10-19), pages 13461 - 13464, XP093155953, ISSN: 0002-7863, DOI: 10.1021/jacs.6b05389
ACOSTA GERARDO A.; ROYO MIRIAM; DE LA TORRE BEATRIZ G.; ALBERICIO FERNANDO: "Facile solid-phase synthesis of head-side chain cyclothiodepsipeptides through a cyclative cleavage from MeDbz-resin", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 58, no. 28, 14 June 2017 (2017-06-14), Amsterdam , NL , pages 2788 - 2791, XP085081569, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2017.06.008
Attorney, Agent or Firm:
INABA, Yoshiyuki et al. (JP)
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