Title:
β-STRAND TYPE CROSSLINKED PEPTIDE
Document Type and Number:
WIPO Patent Application WO/2022/092295
Kind Code:
A1
Abstract:
The present disclosure provides a novel crosslinked peptide. The present disclosure provides a crosslinked peptide that contains a crosslinked portion and a peptide portion, wherein, when the carbon atom at which the crosslinked portion is bonded to the peptide is regarded as being at the α position, then the β position is tertiary or quaternary. The present disclosure provides a novel crosslinked peptide. In particular, the present disclosure provides a crosslinked peptide in which a peptide having no hydrogen bond for inducing or maintaining a secondary structure, for example, a peptide having a β-strand structure, is stably crosslinked.
Inventors:
HAYASHI KAZUHIRO (JP)
MATSUDA MICHIYUKI (JP)
MATSUDA MICHIYUKI (JP)
Application Number:
PCT/JP2021/040138
Publication Date:
May 05, 2022
Filing Date:
October 29, 2021
Export Citation:
Assignee:
XENO INTERFACE INC (JP)
UNIV KYOTO (JP)
UNIV KYOTO (JP)
International Classes:
C07K4/00; A61K38/02
Domestic Patent References:
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ATHERTON, E.SHEPPARD, R. C.: "Solid Phase Peptide Synthesis: A Practical Approach", 1989, IRL PRESS AT OXFORD UNIVERSITY PRESS OXFORD
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ELIEL, E.L.: "Stereochemistry of Carbon Compounds", 1962, MCGRAW-HILL
WILEN, S. H.: "Tables of Resolving Agents and Optical Resolutions", 1972, UNIV. OF NOTRE DAME PRESS, pages: 268
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FISHER BF, J., AM. CHEM. SOC., vol. 138, 2016, pages 10766 - 10769
S. HUNT: "The Non-Protein Amino Acids: In Chemistry and Biochemistry of the Amino Acids", 1985, CHAPMAN AND HALL
BAYLEY, H.: "Photogenerated Reagents in Biochemistry and Molecular Biology", 1983, ELSEVIER
STEWART J. M.YOUNG, J. D.: "The Practice of Peptide Synthesis", 1984, PIERCE CHEMICAL COMPANY
HECHT: "Bioorganic chemistry: Peptides and Proteins", 1998, OXFORD UNIVERSITY PRESS
GRUBBS ET AL., ACC. CHEM. RES., vol. 28, 1995, pages 446 - 452
SCHROCK ET AL., ORGANOMETALLICS, vol. 1, 1982, pages 1645
GALLIVAN ET AL., TETRAHEDRON LETTERS, vol. 46, 2005, pages 2577 - 2580
CROMM, P. M. ET AL.: "Orthogonal ring-closing alkyne and olefinmetathesis for the synthesis of small GTPase-targeting bicyclic peptides", NAT. COMMUN., vol. 7, 2016, pages 11300
HEPPEKAUSEN J ET AL.: "Chem. Eur. J.", vol. 18, 2012, pages: 10281 - 10299
FURSTNER ET AL., J. AM. CHEM. SOC., vol. 118, 1996, pages 12349
M. B. SMITHJ. MARCH: "March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure", 2001, JOHN WILEY SONS
CAREYSUNDBERG: "Advance Organic Chemistry, Part B: Reactions and Synthesis", 1993, PLENUM PRESS
A. R. GENNARO: "Remington's The Science and Practice of Pharmacy,", 2006, LIPPINCOTT, WILLIAMS & WILKINS
"Remington: The Science and Practice of Pharmacy", 2005, LIPPINCOTT WILLIAMS WILKINS
PAUL A. BARTLETT ET AL., J. ORG. CHEM., vol. 47, 1982, pages 393303941
LOUGHLIN WENDY A., TYNDALL JOEL D. A., GLENN MATTHEW P., FAIRLIE DAVID P.: "Update 1 of: beta-strand mimetics", CHEMICAL REVIEWS, vol. 110, 1 January 2010 (2010-01-01), pages PR32 - PR69, XP055925782, DOI: 10.1021/cr900395y
FURSTNER ET AL., J. AM. CHEM. SOC., vol. 121, 1999, pages 9453
CHEM. EUR. J., vol. 7, 2001, pages 5299
ATHERTON, E.SHEPPARD, R. C.: "Solid Phase Peptide Synthesis: A Practical Approach", 1989, IRL PRESS AT OXFORD UNIVERSITY PRESS OXFORD
CARRUTHERS: "Some Modern Methods of Organic Synthesis", 1987, CAMBRIDGE UNIVERSITY PRESS
JACQUES ET AL.: "Enantiomers, Racemates and Resolutions", 1981, WILEY INTERSCIENCE
WILEN ET AL.: "33", TETRAHEDRON, 1977, pages 2725
ELIEL, E.L.: "Stereochemistry of Carbon Compounds", 1962, MCGRAW-HILL
WILEN, S. H.: "Tables of Resolving Agents and Optical Resolutions", 1972, UNIV. OF NOTRE DAME PRESS, pages: 268
SCHAFMEISTER CE ET AL.: "An All-Hydrocarbon Cross-Linking System for Enhancing the Helicity and Metabolic Stability of Peptides", J. AM. CHEM. SOC., vol. 122, 2000, pages 5891 - 5892
BERGE ET AL., J. PHARMACEUTICAL SCIENCES, vol. 66, 1977, pages 1 - 19
FISHER BF, J., AM. CHEM. SOC., vol. 138, 2016, pages 10766 - 10769
S. HUNT: "The Non-Protein Amino Acids: In Chemistry and Biochemistry of the Amino Acids", 1985, CHAPMAN AND HALL
BAYLEY, H.: "Photogenerated Reagents in Biochemistry and Molecular Biology", 1983, ELSEVIER
STEWART J. M.YOUNG, J. D.: "The Practice of Peptide Synthesis", 1984, PIERCE CHEMICAL COMPANY
HECHT: "Bioorganic chemistry: Peptides and Proteins", 1998, OXFORD UNIVERSITY PRESS
GRUBBS ET AL., ACC. CHEM. RES., vol. 28, 1995, pages 446 - 452
SCHROCK ET AL., ORGANOMETALLICS, vol. 1, 1982, pages 1645
GALLIVAN ET AL., TETRAHEDRON LETTERS, vol. 46, 2005, pages 2577 - 2580
CROMM, P. M. ET AL.: "Orthogonal ring-closing alkyne and olefinmetathesis for the synthesis of small GTPase-targeting bicyclic peptides", NAT. COMMUN., vol. 7, 2016, pages 11300
HEPPEKAUSEN J ET AL.: "Chem. Eur. J.", vol. 18, 2012, pages: 10281 - 10299
FURSTNER ET AL., J. AM. CHEM. SOC., vol. 118, 1996, pages 12349
M. B. SMITHJ. MARCH: "March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure", 2001, JOHN WILEY SONS
CAREYSUNDBERG: "Advance Organic Chemistry, Part B: Reactions and Synthesis", 1993, PLENUM PRESS
A. R. GENNARO: "Remington's The Science and Practice of Pharmacy,", 2006, LIPPINCOTT, WILLIAMS & WILKINS
"Remington: The Science and Practice of Pharmacy", 2005, LIPPINCOTT WILLIAMS WILKINS
PAUL A. BARTLETT ET AL., J. ORG. CHEM., vol. 47, 1982, pages 393303941
Attorney, Agent or Firm:
YAMAMOTO, Shusaku et al. (JP)
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