Title:
PEPTIDE COMPOUND PRODUCTION METHOD
Document Type and Number:
WIPO Patent Application WO/2023/136301
Kind Code:
A1
Abstract:
Provided is a method that prevents decreases in solubility in an organic solvent when elongating a peptide chain by a peptide coupling reaction and improves the reactivity of a peptide chain and the operability in a purification process. The method makes it possible to obtain a polypeptide compound represented by formula (P1) by performing amide formation reaction of the carboxyl group on the right side of the amino acid or the peptide compound in formula (R1) with the amino group on the left side of the amino acid or the peptide ester compound in formula (R2) in which the terminal carboxyl group is protected by a silicon-containing hydrophobic substituent TAG(Si).
Inventors:
YAMAMOTO HISASHI (JP)
HATTORI TOMOHIRO (JP)
HATTORI TOMOHIRO (JP)
Application Number:
PCT/JP2023/000653
Publication Date:
July 20, 2023
Filing Date:
January 12, 2023
Export Citation:
Assignee:
CHUBU UNIV EDUCATIONAL FOUNDATION (JP)
International Classes:
C07F7/18; C07K1/06
Domestic Patent References:
| WO2019198833A1 | 2019-10-17 | |||
| WO2021039901A1 | 2021-03-04 | |||
| WO2019069978A1 | 2019-04-11 | |||
| WO2020162393A1 | 2020-08-13 |
Foreign References:
| JP2007078791A | 2007-03-29 | |||
| JP7063408B1 | 2022-05-09 | |||
| JP7063409B1 | 2022-05-09 |
Other References:
WAGNER MICHAEL, HEINER SEBASTIAN, KUNZ HORST: "The (2-Phenyl-2-trimethylsilyl)ethoxycarbonyl (Psoc) Group - A Novel Amino Protecting Group", SYNLETT, GEORG THIEME VERLAG, DE, vol. 2000, no. 12, 1 January 2000 (2000-01-01), DE , pages 1753 - 1756, XP093078983, ISSN: 0936-5214, DOI: 10.1055/s-2000-8677
HATTORI, TOMOHIRO; WATARU, MURAMATSU; HISASHI, YAMAMOTO: "Substrate-Controlled Amide Bond Formation: Innovation of Peptide Synthesis", JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY, JAPAN, vol. 79, no. 5, 1 January 2021 (2021-01-01), pages 382 - 390, XP009547744, ISSN: 1883-6526, DOI: 10.5059/yukigoseikyokaishi.79.382
LIU, Y. ; YAMAZAKI, S. ; IZUHARA, S.: "Modification and chemical transformation of Si(111) surface", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 691, no. 26, 15 December 2006 (2006-12-15), AMSTERDAM, NL , pages 5809 - 5824, XP028048325, ISSN: 0022-328X, DOI: 10.1016/j.jorganchem.2006.09.048
WAGNER MICHAEL, KUNZ HORST: "(2-Phenyl-2-trimethylsilyl)ethyl (PTMSE) Esters - a Novel Carboxyl Protecting Group", SYNLETT, GEORG THIEME VERLAG, DE, vol. 2000, no. 3, 1 January 2000 (2000-01-01), DE , pages 400 - 402, XP093078989, ISSN: 0936-5214, DOI: 10.1055/s-2000-6513
FUSTERO SANTOS, SANCHO AMADOR GARCÍA, CHIVA GEMA, SANZ-CERVERA JUAN F., DEL POZO CARLOS, ACEÑA JOSÉ LUIS: "Fluorous (Trimethylsilyl)ethanol: A New Reagent for Carboxylic Acid Tagging and Protection in Peptide Synthesis", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 71, no. 8, 1 April 2006 (2006-04-01), pages 3299 - 3302, XP093078992, ISSN: 0022-3263, DOI: 10.1021/jo052569u
HATTORI, TOMOHIRO; WATARU, MURAMATSU; HISASHI, YAMAMOTO: "Substrate-Controlled Amide Bond Formation: Innovation of Peptide Synthesis", JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY, JAPAN, vol. 79, no. 5, 1 January 2021 (2021-01-01), pages 382 - 390, XP009547744, ISSN: 1883-6526, DOI: 10.5059/yukigoseikyokaishi.79.382
LIU, Y. ; YAMAZAKI, S. ; IZUHARA, S.: "Modification and chemical transformation of Si(111) surface", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 691, no. 26, 15 December 2006 (2006-12-15), AMSTERDAM, NL , pages 5809 - 5824, XP028048325, ISSN: 0022-328X, DOI: 10.1016/j.jorganchem.2006.09.048
WAGNER MICHAEL, KUNZ HORST: "(2-Phenyl-2-trimethylsilyl)ethyl (PTMSE) Esters - a Novel Carboxyl Protecting Group", SYNLETT, GEORG THIEME VERLAG, DE, vol. 2000, no. 3, 1 January 2000 (2000-01-01), DE , pages 400 - 402, XP093078989, ISSN: 0936-5214, DOI: 10.1055/s-2000-6513
FUSTERO SANTOS, SANCHO AMADOR GARCÍA, CHIVA GEMA, SANZ-CERVERA JUAN F., DEL POZO CARLOS, ACEÑA JOSÉ LUIS: "Fluorous (Trimethylsilyl)ethanol: A New Reagent for Carboxylic Acid Tagging and Protection in Peptide Synthesis", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 71, no. 8, 1 April 2006 (2006-04-01), pages 3299 - 3302, XP093078992, ISSN: 0022-3263, DOI: 10.1021/jo052569u
Attorney, Agent or Firm:
AOKI, Atsushi et al. (JP)
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