Glytech, Inc.

Ryo Okamoto

Yasuhiro Kajihara

Kazuyuki Ishii

Izumi Sakamoto

Takefumi Murase

Rie Nishikawa

Kota Nomura

Takuya Haraguchi

Yuta Maki

Masayuki Izumi

Yoko Amazaki

Motoharu Kimura

An object of the present invention is to provide a novel method having high efficiency and versatility for a peptide thioester and peptide. The present invention provides a method for producing a peptide thioester, comprising the steps of: (1) providing a peptide thioester having a CGC triplet at the C-terminal; (2) causing a transfer between an SH group of the C-terminal cysteine and a carbonyl group of the glycine in the CGC triplet to obtain an R-X-CG-thioester; and (3) causing, in the R-X-CG-thioester, a transfer between the SH group of the cysteine and a carbonyl group of X, and a transfer between an amino group of the cysteine and a thiol group of the glycine to obtain a peptide thioester, and a method for producing a peptide using the peptide thioester produced by this method.

Methods for producing peptide thioester and peptide

The object of the present invention is to provide a method for manufacturing an amino acid polymer more simply and efficiently compared to conventional methods for manufacturing amino acid polymers. The present invention provides a method for manufacturing an amino acid polymer with thioacid amino acids. Specifically, the manufacturing method of the present invention comprises (A) a step of preparing first and second thioacid amino acids, (B) a step of subjecting said first and second thioacid amino acids to an oxidation reaction to obtain an amino acid polymer linked by peptide bonds. The manufacturing method of the present invention is characterized in that it partially uses thioacid amino acids that do not possess a protecting group.

Production method for amino-acid polymer

A process for chemically converting a peptide chain into a peptide thioester includes, when a &#x2014;C(&#x2550;X)&#x2014;Rgroup is introduced to the thiol group of the cysteine residue and then the resulting peptide is reacted with a compound having a leaving group represented by the formula: &#x2014;NH&#x2014;C(&#x2550;Y)NHRin an organic solvent, the &#x2014;NH&#x2014;C(&#x2550;Y)NHRgroup binds via addition reaction to the carboxyl group of the N-terminal-side peptide bond of the cysteine residue, whereby the peptide bond is cleaved and the C-terminal-side peptide fragment is cut off. Further, when the resulting peptide chain having the &#x2014;NH&#x2014;C(&#x2550;Y)NHRgroup is reacted with a thiol in a buffer solution, a thiol exchange reaction occurs, namely, the thiol group of the thiol binds to the carbonyl carbon to which the &#x2014;NH&#x2014;C(&#x2550;Y)NHRgroup has bound, whereby the &#x2014;NH&#x2014;C(&#x2550;Y)NHRgroup is eliminated.

Process for production of peptide thioester

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Osaka, Japan

Ryo Okamoto