Method for producing peptide thioester

Details Method for producing peptide thioester Method for producing peptide thioester

2006-10-25

2011-12-13

Tsang, Cecilia J (Department: 1654)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Peptide containing doai

C514S020900, C530S324000, C508S344000

Reexamination Certificate

active

08076299

ABSTRACT:
It is an object of the present invention to provide a novel method for producing a peptide thioester. In the present invention, general peptide synthesis is performed on a solid-phase resin, carboxylic acid obtained after cutout is allowed to react with p-toluenesulfonyl isocyanate, and then the reaction product is alkylated, and is reacted with thiol. Thus, peptide thioester is simply synthesized under mild conditions.

REFERENCES:
patent: 2003/0191291 (2003-10-01), Kochendoerfer et al.
patent: 2004-508338 (2004-03-01), None
patent: 2004-508383 (2004-03-01), None
patent: 02/20557 (2002-03-01), None
patent: 03/070764 (2003-08-01), None
He, Organic Letters, 2006, 8, 2483-2485.
Kerber, 1968, The journal of Organic Chemistry, 33, 4442-4445.
English Traslation of JP 2007/049635, Traslation date: Aug. 9, 2011.
English Traslation of Foreign priority document: Japan 2005-30953 Oct. 25, 2005 filed on Aug. 18, 2011 by applicants.
Ten Holte et al., “Solid-Phase Synthesis of 3,5-Disubstituted 1,3-Oxazolidin-2-ones by an Activation/Cyclo-elimination Process”,Tetrahedron Lett., vol. 39, pp. 7407-7410 (1998).
Li et al., “Direct Preparation of Peptide Thioesters Using an Fmoc Solid-Phase Method”,Tetrahedron Lett., vol. 39, pp. 8669-8672 (1998).
Ingenito et al., “Solid-Phase Synthesis of Peptide C-Terminal Thioesters by Fmoc/t-Bu Chemistry”,J. Am. Chem. Soc., vol. 121, pp. 11369-11374 (1999).
Sewing et al., “Fmoc-Compatible Solid-Phase Peptide Synthesis of Long C-Terminal Peptide Thioesters”,Angew. Chem. Int. Ed., vol. 40, No. 18, pp. 3395-3396 (2001).
Brask et al., “Fmoc Solid-Phase Synthesis of Peptide Thioesters by Masking as Trithioortho Esters”,Org. Lett., vol. 5, pp. 2951-2953 (2003).
Botti et al., “Native Chemical Ligation through in Situ O to S Acyl Shift”,Org. Lett., vol. 6, pp. 4861-4864 (2004).
Ollivier et al., “Fmoc Solid-Phase Synthesis of Peptide Thioesters Using an IntramolecularN,S-Acyl Shift”,Org. Lett., vol. 7, pp. 2647-2650 (2005).

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