Method for production of peptide thioester compound

Details Method for production of peptide thioester compound Method for production of peptide thioester compound

2007-03-28

2011-11-15

Russel, Jeffrey E (Department: 1654)

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Synthesis of peptides

C530S345000

Reexamination Certificate

active

08058394

ABSTRACT:
The present invention provides a process for producing a peptide thioester compound. The process involves: (A) forming a peptide by a solid-phase synthesis method using a resin modified with a linker represented by the formula (1) as a solid phase:wherein R1represents C1-4alkyl group, R2represents hydrogen atom or C1-4alkoxy group, and n represents an integer of 1 to 4; (B) cleaving a bond between the solid phase and the peptide with at least one acid selected from dilute hydrochloric acid, dilute sulfuric acid, formic acid, and acetic acid to produce a peptide having a carboxyl group at the C-terminus; and (C) reacting a thiol compound with the peptide at −100 to 0° C. in the presence of a condensing agent in a solvent.

REFERENCES:
patent: 7135566 (2006-11-01), Kajihara et al.
patent: 2004/0181054 (2004-09-01), Kajihara et al.
patent: 2005/0222382 (2005-10-01), Kajihara
patent: 1 961 764 (2008-08-01), None
patent: WO 03/008431 (2003-01-01), None
patent: WO 2004/005330 (2004-01-01), None
patent: WO 2005/095331 (2005-10-01), None
patent: WO 2007/063907 (2007-06-01), None
Clippingdale, Andrew B., et al.—“Peptide Thioester Preparation by Fmoc Solid Phase Peptide Synthesis for Use in Native Chemical Ligation”,Journal of Peptide Science, 6: pp. 225-234; (2000).
Ingenito, Raffaele, et al.—“Solid Phase Synthesis of Peptide C-Terminal Thioesters by Fmoc/t-Bu Chemistry”—Journal American Chemical Society—pp. 11369-11374.—Nov. 25, 1999.
Mezzato, Stefano, et al.—“An Orthogonal Double-Linker Resin Facilitates the Efficient Solid-Phase Synthesis of Complex-Type N-Glycopeptide Thioesters Suitable for Native Chemical Ligation”—Angew. Chem. Int. Ed.—vol. 44, pp. 1650-1654.—2005.
Futaki, Shiroh, et al.—“Preparation of Peptide Thioesters using Fmoc-Solid-Phase Peptide Synthesis and its Application to the Construction of a Template-Assembled Synthetic Protein (TASP)”—Tetrahedron Letters., vol. 44, pp. 6237-6240.—1997.
Von Eggelkraut-Gottanka, Regula, et al.—“Peptide Thioester Formation Using Standard Fmoc-chemistry”—Tetrahedron Letters 44 (Feb. 28, 2003), pp. 3551-3554.
Mezo, Adam R., et al.—“Oligomerization of Uniquely Folded Mini-Protein Motifs: Development of a Homotrimeric ββα Peptide”—Journal American Chemical Society—(Apr. 6, 2001), pp. 3885-3891.
Riniker, Bernhard, et al.—“A General Strategy for the Synthesis of Large Peptides: The Combined Solid-Phase and Solution Approach.”—Tetrahedron Letters vol. 49, No. 41, (Apr. 22, 1993), pp. 9307-9320.
Nakahara, Yoshiaki,—“Problems and Progress in Glycopeptide Synthesis”—Trends in Glycoscience and Glycotechnology, vol. 15, No. 85, (Sep. 2003), pp. 257-273.
Kajihara, Yasuhiro, et al.—“Prompt Chemoenzymatic Synthesis of Diverse Complex-Type Oligosaccharides and Its Application to the Solid-Phase Synthesis of a Glycopeptide with Asn- Linked Sialyl-undeca- and Asialo-nanasaccharides”—Chem. Eur. Journal, vol. 10, (2004), pp. 971-985.
Kajihara, Yasuhiro, et al. —“Convenient Synthesis of a Sialylglycopeptide-thioester Having an Intact and Homogeneous Complex-type Disialyl-Oligosaccharide”—Carbohydrate Research 341 (2006), pp. 1333-1340.

Affiliated with

Also associated with

Rating

Method for production of peptide thioester compound does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method for production of peptide thioester compound, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method for production of peptide thioester compound will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-4275654