Title:
PEPTIDE AND METHOD FOR MANUFACTURING SAME
Document Type and Number:
WIPO Patent Application WO/2021/002408
Kind Code:
A1
Abstract:
The present invention provides a peptide having a fluoroalkyl group as a side chain. The present invention is a method for manufacturing a fluoroalkyl-group-containing peptide in which a compound represented by general formula (6-2) or (6-4) (* indicates that the absolute configuration of an asymmetric carbon atom indicated by * is S or R; Rf is a C1-30 alkyl group (if the C1-30 alkyl group is a C2-30 alkyl group, there may be 1 to 5 ether-bonding oxygen atoms between the carbon atoms) substituted by at least two fluorine atoms and which may further be substituted by halogen atoms other than fluorine atoms; and R2 is a protection group of an amino group) is condensed with a fluorine-containing amino acid in which the carboxy group is protected, an amino acid in which the carboxy group is protected, a fluorine-containing peptide in which the C-terminus is protected, or a peptide in which the C-terminus is protected.
Inventors:
OKAZOE TAKASHI (JP)
ISHIBASHI YUICHIRO (JP)
SANDO SHINSUKE (JP)
MORIMOTO JUMPEI (JP)
AIKAWA KOHSUKE (JP)
MIKAMI TOSHIKI (JP)
ONO TAKAHIRO (JP)
ISHIBASHI YUICHIRO (JP)
SANDO SHINSUKE (JP)
MORIMOTO JUMPEI (JP)
AIKAWA KOHSUKE (JP)
MIKAMI TOSHIKI (JP)
ONO TAKAHIRO (JP)
Application Number:
PCT/JP2020/025912
Publication Date:
January 07, 2021
Filing Date:
July 01, 2020
Export Citation:
Assignee:
AGC INC (JP)
UNIV TOKYO (JP)
UNIV TOKYO (JP)
International Classes:
C07C231/12; C07C237/12; C07C269/06; C07C271/22; C07K1/06; C07K1/10; C07K5/00; C07K5/08; C07K5/083
Domestic Patent References:
| WO2008089491A2 | 2008-07-24 |
Foreign References:
| US20100099845A1 | 2010-04-22 | |||
| US20090259020A1 | 2009-10-15 | |||
| JP2019124016A | 2019-07-25 | |||
| JP2019209908A | 2019-12-12 | |||
| US6316003B1 | 2001-11-13 | |||
| US6306993B1 | 2001-10-23 |
Other References:
CHIU HSIEN-PO, SUZUKI YUTA, GULLICKSON DONALD, AHMAD RAHEEL, KOKONA BASHKIM, FAIRMAN ROBERT, CHENG RICHARD P.: "Helix Propensity of Highly Fluorinated Amino Acids", J. AM. CHEM. SOC., vol. 128, 2006, pages 15556 - 15557, XP055784078
LEE KYUNG-HOON, LEE HYANG-YEOL, SLUTSKY MORRIS M., ANDERSON JAMES T., MARSH E. NEIL G.: "Fluorous Effect in Proteins: De Novo Design and Characterization of a Four-a-Hel ix Bundle Protein Containing Hexafluoroleucine", BIOCHEMISTRY, vol. 43, 2004, pages 16277 - 16284, XP055784092
HAJIME ABE, HIDEKI AMII, AND KENJI UNEYAMA: "Pd-Catalyzed Asymmetric Hydrogenation of alpha-Fluorinated Iminoesters in Fluorinated Alcohol: A New and Catalytic Enantioselective Synthesis of Fluoro alpha-Amino Acid Derivatives", ORGANIC LETTERS, vol. 3, no. 3, 2001, pages 313 - 315, XP055784094
SHUNKI MIKAMI , KOSUKE AIKAWA, JUNPEI MORIMOTO, SHINSUKE SHANDONG, KYOKO NOZAKI,TAKASHI: "Synthesis of novel fluorine-containing amino acids and application to cell membrane permeable peptides", LECTURE ABSTRACTS OF THE 42ND FLUORINE CONFERENCE OF JAPAN; NOVEMBER 21-22, 2019, vol. 42, 21 November 2019 (2019-11-21) - 22 November 2019 (2019-11-22), JP, pages 142 - 143, XP009532711, ISSN: 2436-0260
MIYAJI ET AL., DRUG METABOLISM AND DISPOSITION, vol. 39, 2011, pages 1946 - 1953
SAKAI ET AL., TETRAHEDRON, vol. 52, no. 1, 1996, pages 233 - 244
FARACIWALSH, BIOCHEMISTRY, vol. 28, no. 2, 1989, pages 431 - 437
ZHANG ET AL., MRS COMMUNICATIONS, vol. 8, 2018, pages 303 - 313
CAI ET AL., ACS APPLIED MATERIALS AND INTERFACES, vol. 8, 2016, pages 5821 - 5832
JOURNAL OF FLUORINE CHEMISTRY, vol. 26, 1984, pages 341 - 358
CHEMICAL AND PHARMACEUTICAL BULLETIN, vol. 35, 1987, pages 468
LIEBIGS ANNALEN DER CHEMIE, vol. 12, 1990, pages 1175 - 1183
See also references of EP 3995486A4
LEE KYUNG-HOON, LEE HYANG-YEOL, SLUTSKY MORRIS M., ANDERSON JAMES T., MARSH E. NEIL G.: "Fluorous Effect in Proteins: De Novo Design and Characterization of a Four-a-Hel ix Bundle Protein Containing Hexafluoroleucine", BIOCHEMISTRY, vol. 43, 2004, pages 16277 - 16284, XP055784092
HAJIME ABE, HIDEKI AMII, AND KENJI UNEYAMA: "Pd-Catalyzed Asymmetric Hydrogenation of alpha-Fluorinated Iminoesters in Fluorinated Alcohol: A New and Catalytic Enantioselective Synthesis of Fluoro alpha-Amino Acid Derivatives", ORGANIC LETTERS, vol. 3, no. 3, 2001, pages 313 - 315, XP055784094
SHUNKI MIKAMI , KOSUKE AIKAWA, JUNPEI MORIMOTO, SHINSUKE SHANDONG, KYOKO NOZAKI,TAKASHI: "Synthesis of novel fluorine-containing amino acids and application to cell membrane permeable peptides", LECTURE ABSTRACTS OF THE 42ND FLUORINE CONFERENCE OF JAPAN; NOVEMBER 21-22, 2019, vol. 42, 21 November 2019 (2019-11-21) - 22 November 2019 (2019-11-22), JP, pages 142 - 143, XP009532711, ISSN: 2436-0260
MIYAJI ET AL., DRUG METABOLISM AND DISPOSITION, vol. 39, 2011, pages 1946 - 1953
SAKAI ET AL., TETRAHEDRON, vol. 52, no. 1, 1996, pages 233 - 244
FARACIWALSH, BIOCHEMISTRY, vol. 28, no. 2, 1989, pages 431 - 437
ZHANG ET AL., MRS COMMUNICATIONS, vol. 8, 2018, pages 303 - 313
CAI ET AL., ACS APPLIED MATERIALS AND INTERFACES, vol. 8, 2016, pages 5821 - 5832
JOURNAL OF FLUORINE CHEMISTRY, vol. 26, 1984, pages 341 - 358
CHEMICAL AND PHARMACEUTICAL BULLETIN, vol. 35, 1987, pages 468
LIEBIGS ANNALEN DER CHEMIE, vol. 12, 1990, pages 1175 - 1183
See also references of EP 3995486A4
Attorney, Agent or Firm:
T.S. PARTNERS et al. (JP)
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