Title:
PROCESS FOR PRODUCTION OF PEPTIDE THIOESTER
Document Type and Number:
WIPO Patent Application WO/2008/044628
Kind Code:
A1
Abstract:
Disclosed is a process for synthesizing a desired peptide thioester by using a readily available compound within a relatively short period under such conditions where any side reaction is hardly caused. In the method, a peptide chain is elongated by Fmoc method utilizing an N-alkylcysteine as the C-terminal amino acid. After the deprotection is completed, the N-S transfer of a peptide bond to a thiol group in the N- alkylcysteine is conducted under weakly acidic conditions, thereby forming a thioester bond.
Inventors:
HOJO HIRONOBU (JP)
NAKAHARA YOSHIAKI (JP)
NAKAHARA YOSHIAKI (JP)
Application Number:
PCT/JP2007/069555
Publication Date:
April 17, 2008
Filing Date:
October 05, 2007
Export Citation:
Assignee:
UNIV TOKAI EDUCATIONAL SYSTEM (JP)
HOJO HIRONOBU (JP)
NAKAHARA YOSHIAKI (JP)
HOJO HIRONOBU (JP)
NAKAHARA YOSHIAKI (JP)
International Classes:
C07K1/113; C07C319/20; C07C323/58; C07K1/08
Foreign References:
| JP2002526387A | 2002-08-20 | |||
| JP2002030050A | 2002-01-29 | |||
| JPS5553248A | 1980-04-18 | |||
| JPH11217397A | 1999-08-10 | |||
| JPH11217397A | 1999-08-10 |
Other References:
LIU J.-F. ET AL.: "A Convenient Synthesis of N-Fluorenylmethoxycarbonyl-N-Methyl-L-Cysteine Derivatives [Fmoc,Me-Cys(R)-OH]", SYNTHESIS, no. 11, 2002, pages 1499 - 1501, XP003022163
OZAWA C. ET AL.: "Synthesis of Glycopeptide Dendrimer with Thioester Prepared by a new Method", THE JAPANESE SOCIETY OF CARBOHYDRATE RESEARCH NENKAI YOSHISHU, vol. 27, 10 July 2007 (2007-07-10), pages 135, XP003022164
BAYO-PUXAN N. ET AL.: "Total Solid-Phase Synthesis of the Azathiocoraline Class of Symmetric Bicyclic Peptides", CHEM. EUR. J., vol. 12, 4 December 2006 (2006-12-04), pages 9001 - 9009, XP002513162, DOI: doi:10.1002/chem.200600815
HIRONOBU HOJO ET AL.: "N-Alkyl cysteine-assisted thioesterification of peptides", TETRAHEDRON LETTERS, vol. 48, no. 1, 1 January 2007 (2007-01-01), pages 25 - 28, XP005785943
TORU KAWAKAMI ET AL.: "Peptide Thioester preparation based on an N-S acyl shift reaction mediated by a thiol ligation auxiliary", TETRAHEDRON LETTERS, vol. 46, 2005, pages 8805 - 8807, XP005161812
UEKI, A. ET AL., TETRAHEDRON, vol. 63, 2007, pages 2170 - 2181
See also references of EP 2085403A4
OZAWA C. ET AL.: "Synthesis of Glycopeptide Dendrimer with Thioester Prepared by a new Method", THE JAPANESE SOCIETY OF CARBOHYDRATE RESEARCH NENKAI YOSHISHU, vol. 27, 10 July 2007 (2007-07-10), pages 135, XP003022164
BAYO-PUXAN N. ET AL.: "Total Solid-Phase Synthesis of the Azathiocoraline Class of Symmetric Bicyclic Peptides", CHEM. EUR. J., vol. 12, 4 December 2006 (2006-12-04), pages 9001 - 9009, XP002513162, DOI: doi:10.1002/chem.200600815
HIRONOBU HOJO ET AL.: "N-Alkyl cysteine-assisted thioesterification of peptides", TETRAHEDRON LETTERS, vol. 48, no. 1, 1 January 2007 (2007-01-01), pages 25 - 28, XP005785943
TORU KAWAKAMI ET AL.: "Peptide Thioester preparation based on an N-S acyl shift reaction mediated by a thiol ligation auxiliary", TETRAHEDRON LETTERS, vol. 46, 2005, pages 8805 - 8807, XP005161812
UEKI, A. ET AL., TETRAHEDRON, vol. 63, 2007, pages 2170 - 2181
See also references of EP 2085403A4
Attorney, Agent or Firm:
SIKs & Co. (Kyobashi-Nisshoku Bldg.8-7, Kyobashi 1-chome,Chuo-k, Tokyo 31, JP)
Download PDF: