Title:
METHOD FOR PRODUCING PEPTIDE HYDRAZIDE, PEPTIDE AMIDE, AND PEPTIDE THIOESTER
Document Type and Number:
WIPO Patent Application WO/2015/068532
Kind Code:
A1
Abstract:
The purpose of the present invention is to provide a method for producing peptide thioester compounds, peptide hydrazide compounds, and peptide amide compounds. The present invention provides a method for producing peptide hydrazide compounds or peptide amide compounds by using a compound represented by general formula (2) [in the formula, R1, R2, R3, and X are as defined in the specification] as the starting raw material and using a hydrazine compound or an ammonia compound in a reaction reagent. The present invention also provides a method for producing peptide thioester compounds from the peptide hydrazide compounds.
Inventors:
OTAKA AKIRA (JP)
SHIGENAGA AKIRA (JP)
SUGIYAMA MASAKAZU (JP)
FUJII HIDEMI (JP)
SHIGENAGA AKIRA (JP)
SUGIYAMA MASAKAZU (JP)
FUJII HIDEMI (JP)
Application Number:
PCT/JP2014/077271
Publication Date:
May 14, 2015
Filing Date:
October 10, 2014
Export Citation:
Assignee:
AJINOMOTO KK (JP)
International Classes:
C07K1/02; C07K1/04; C07K1/06; C07K1/107; C07K1/13
Domestic Patent References:
| WO1999065931A1 | 1999-12-23 |
Foreign References:
| CN102199214A | 2011-09-28 | |||
| JPH06504676A | 1994-06-02 | |||
| JP2005536470A | 2005-12-02 | |||
| JPH1171396A | 1999-03-16 |
Other References:
YURIE KANEMITSU ET AL.: "S-cyanyl Cysteine Zanki Bui deno Sentakuteki Hydrazide-ka Hanno o Riyo shita Shinki Peptide Thioester Goseiho no Kaihatsu Kenkyu", 94TH ANNUAL MEETING OF THE CHEMICAL SOCIETY OF JAPAN IN SPRING (2014) KOEN YOSHISHU IV, March 2014 (2014-03-01), pages 1472
ADAMS, AL. ET AL.: "Cysteine promoted C- terminal hydrazinolysis of native peptides and proteins", ANGEW. CHEM. INT. ED. ENGL., vol. 52, no. 49, October 2013 (2013-10-01), pages 13062 - 13066
FANG, GM. ET AL.: "Protein chemical synthesis by ligation of peptide hydrazides", ANGEW. CHEM. INT. ED. ENGL., vol. 50, no. 33, 2011, pages 7645 - 7649
STEMMLER EA . ET AL.: "C-terminal methylation of truncated neuropeptides: an enzyme-assisted extraction artifact involving methanol", PEPTIDES, vol. 46, 2013, pages 108 - 125
AKIRA SHIGENAGA ET AL.: "Recent Progress in the Synthetic Methodologies of Peptide Thioesters", JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY, vol. 68, no. 9, 2010, JAPAN, pages 911 - 919
CHANDRUDU, S. ET AL.: "Chemical methods for peptide and protein production", MOLECULES, vol. 18, no. 4, April 2013 (2013-04-01), pages 4373 - 4388
ADAMS, AL. ET AL.: "Cysteine promoted C- terminal hydrazinolysis of native peptides and proteins", ANGEW. CHEM. INT. ED. ENGL., vol. 52, no. 49, October 2013 (2013-10-01), pages 13062 - 13066
FANG, GM. ET AL.: "Protein chemical synthesis by ligation of peptide hydrazides", ANGEW. CHEM. INT. ED. ENGL., vol. 50, no. 33, 2011, pages 7645 - 7649
STEMMLER EA . ET AL.: "C-terminal methylation of truncated neuropeptides: an enzyme-assisted extraction artifact involving methanol", PEPTIDES, vol. 46, 2013, pages 108 - 125
AKIRA SHIGENAGA ET AL.: "Recent Progress in the Synthetic Methodologies of Peptide Thioesters", JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY, vol. 68, no. 9, 2010, JAPAN, pages 911 - 919
CHANDRUDU, S. ET AL.: "Chemical methods for peptide and protein production", MOLECULES, vol. 18, no. 4, April 2013 (2013-04-01), pages 4373 - 4388
Attorney, Agent or Firm:
SAEGUSA & PARTNERS (JP)
Patent business corporation 3 Edakuni [Hajime] patent firm (JP)
Patent business corporation 3 Edakuni [Hajime] patent firm (JP)
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