Title:
PEPTIDE COMPOUND PRODUCTION METHOD AND AMIDATION AGENT
Document Type and Number:
WIPO Patent Application WO/2022/255195
Kind Code:
A1
Abstract:
The present invention provides a method for inexpensively and efficiently synthesizing polypeptide compounds comprising various amino acids. The method involves (i) inducing an amide formation reaction between the carboxyl group on the right side in the formula of the amino acid or peptide compound represented by formula (R1) and the amino group on the left side in the formula of the amino acid ester or peptide ester compound represented by formula (R2) in the presence of an aluminum compound represented by formula (A) to obtain a peptide compound represented by formula (P1) (the definitions of the reference signs in the formula are as presented in the description).
Inventors:
YAMAMOTO HISASHI (JP)
HATTORI TOMOHIRO (JP)
HATTORI TOMOHIRO (JP)
Application Number:
PCT/JP2022/021434
Publication Date:
December 08, 2022
Filing Date:
May 25, 2022
Export Citation:
Assignee:
CHUBU UNIV EDUCATIONAL FOUNDATION (JP)
International Classes:
C07K1/08
Domestic Patent References:
| WO2009060843A1 | 2009-05-14 | |||
| WO2017204144A1 | 2017-11-30 | |||
| WO2018199146A1 | 2018-11-01 | |||
| WO2018199147A1 | 2018-11-01 | |||
| WO2019208731A1 | 2019-10-31 | |||
| WO2021085635A1 | 2021-05-06 | |||
| WO2021085636A1 | 2021-05-06 | |||
| WO2021149814A1 | 2021-07-29 |
Foreign References:
| JP2009507906A | 2009-02-26 |
Other References:
MARTIN, S.F. DWYER, M.P. LYNCH, C.L.: "Application of AlMe3-mediated amidation reactions to solution phase peptide synthesis", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 39, no. 12, 19 March 1998 (1998-03-19), Amsterdam , NL , pages 1517 - 1520, XP004108088, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(98)00071-9
MURAMATSU WATARU, HATTORI TOMOHIRO, YAMAMOTO HISASHI: "Substrate-Directed Lewis-Acid Catalysis for Peptide Synthesis", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 141, no. 31, 16 July 2019 (2019-07-16), pages 12288 - 12295, XP055930667, ISSN: 0002-7863, DOI: 10.1021/jacs.9b03850
MURAMATSU WATARU, HATTORI TOMOHIRO, YAMAMOTO HISASHI: "Game Change from Reagent- to Substrate-Controlled Peptide Synthesis", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOCIETY OF JAPAN,NIPPON KAGAKUKAI, JP, vol. 93, no. 6, 15 June 2020 (2020-06-15), JP , pages 759 - 767, XP055930673, ISSN: 0009-2673, DOI: 10.1246/bcsj.20200057
CHUNG: "Trimethylaluminium-Facilitated Direct Amidation of Carboxylic Acids", SYNLETT, vol. 14, 1 January 2011 (2011-01-01), pages 2072 - 2074, XP055132481
LI JIANQING, SUBRAMANIAM KRISHNANANTHAN, SMITH DANIEL, QIAO JENNIFER X., LI JIE JACK, QIAN-CUTRONE JINGFANG, KADOW JOHN F., VITE G: "AlMe 3 -Promoted Formation of Amides from Acids and Amines", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 14, no. 1, 6 January 2012 (2012-01-06), US , pages 214 - 217, XP093009377, ISSN: 1523-7060, DOI: 10.1021/ol203007s
DUBOIS NATHALIE; GLYNN DANIEL; MCINALLY THOMAS; RHODES BARRIE; WOODWARD SIMON; IRVINE DEREK J.; DODDS CHRIS: "On DABAL-Me3promoted formation of amides", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 69, no. 46, 1 January 1900 (1900-01-01), AMSTERDAM, NL , pages 9890 - 9897, XP028732810, ISSN: 0040-4020, DOI: 10.1016/j.tet.2013.08.062
CHEM. REV., vol. 111, 2011, pages 6557 - 6602
ORG. PROCESS RES. DEV., vol. 20, no. 2, 2016, pages 140 - 177
CHEM. REV., vol. 116, 2016, pages 12029 - 12122
SCIENCE, vol. 256, 1992, pages 221 - 225
ANGEW. CHEM. INT. ED., vol. 45, 2006, pages 1248 - 1252
CHEM. EUR. J., vol. 25, 2019, pages 15091
ORG. LETT., vol. 22, 2020, pages 8039
CHEM. EUR. J., vol. 24, 2018, pages 7033
SYNLETT, 2011, pages 2072 - 2074
MURAMATSU WATARU, HATTORI TOMOHIRO, YAMAMOTO HISASHI: "Substrate-Directed Lewis-Acid Catalysis for Peptide Synthesis", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 141, no. 31, 16 July 2019 (2019-07-16), pages 12288 - 12295, XP055930667, ISSN: 0002-7863, DOI: 10.1021/jacs.9b03850
MURAMATSU WATARU, HATTORI TOMOHIRO, YAMAMOTO HISASHI: "Game Change from Reagent- to Substrate-Controlled Peptide Synthesis", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOCIETY OF JAPAN,NIPPON KAGAKUKAI, JP, vol. 93, no. 6, 15 June 2020 (2020-06-15), JP , pages 759 - 767, XP055930673, ISSN: 0009-2673, DOI: 10.1246/bcsj.20200057
CHUNG: "Trimethylaluminium-Facilitated Direct Amidation of Carboxylic Acids", SYNLETT, vol. 14, 1 January 2011 (2011-01-01), pages 2072 - 2074, XP055132481
LI JIANQING, SUBRAMANIAM KRISHNANANTHAN, SMITH DANIEL, QIAO JENNIFER X., LI JIE JACK, QIAN-CUTRONE JINGFANG, KADOW JOHN F., VITE G: "AlMe 3 -Promoted Formation of Amides from Acids and Amines", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 14, no. 1, 6 January 2012 (2012-01-06), US , pages 214 - 217, XP093009377, ISSN: 1523-7060, DOI: 10.1021/ol203007s
DUBOIS NATHALIE; GLYNN DANIEL; MCINALLY THOMAS; RHODES BARRIE; WOODWARD SIMON; IRVINE DEREK J.; DODDS CHRIS: "On DABAL-Me3promoted formation of amides", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 69, no. 46, 1 January 1900 (1900-01-01), AMSTERDAM, NL , pages 9890 - 9897, XP028732810, ISSN: 0040-4020, DOI: 10.1016/j.tet.2013.08.062
CHEM. REV., vol. 111, 2011, pages 6557 - 6602
ORG. PROCESS RES. DEV., vol. 20, no. 2, 2016, pages 140 - 177
CHEM. REV., vol. 116, 2016, pages 12029 - 12122
SCIENCE, vol. 256, 1992, pages 221 - 225
ANGEW. CHEM. INT. ED., vol. 45, 2006, pages 1248 - 1252
CHEM. EUR. J., vol. 25, 2019, pages 15091
ORG. LETT., vol. 22, 2020, pages 8039
CHEM. EUR. J., vol. 24, 2018, pages 7033
SYNLETT, 2011, pages 2072 - 2074
Attorney, Agent or Firm:
AOKI, Atsushi et al. (JP)
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