Method for producing cyclized peptide having intramolecular S-S bond
AssigneeAjinomoto Co., Inc.
InventorsDaisuke Takahashi, Tatsuji Inomata, Yuki Shinohara
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Abstract
Cyclized peptides having a crosslinked structure by one or more intramolecular S—S bonds may be prepared by: (1-A) as to a completely protected linear peptide having two or more SH groups as functional groups on the peptide, removing protecting groups of all functional groups other than the protected SH groups in the peptide, (1-B) protecting all SH groups of the linear peptide having two or more SH groups as the functional groups on the peptide by forming a temporary S—S bond, and (2) subjecting the peptide obtained by step (1-A) and step (1-B) to a folding step under oxidation and reduction conditions to obtain the cyclized peptide by re-forming an S—S bond in the peptide molecule.
Claims31
A method for producing a cyclized peptide from a linear peptide, wherein:
- the linear peptide comprises two or more SH groups as functional groups,
- all SH groups are protected,
- an N terminal amino group is optionally protected, and
- all of a C-terminal carboxy group and other functional groups on the peptide are protected,
- the method comprising:
- (1-A) removing protecting groups of all functional groups other than the protected SH groups in the linear peptide;
- (1-B) forming a temporary S—S bond to protect all SH groups of the linear peptide;
- wherein the peptide obtained from following both (1-A) and (1-B) in any order or both simultaneously is an S-protected peptide,
- wherein, in the S-protected peptide:
- two or more SH groups are present as the functional groups on the peptide,
- all SH groups are protected by formation of a temporary S—S bond, and
- all protecting groups of other functional groups on the peptide are removed, and
- (2) folding the S-protected peptide under oxidation and reduction conditions to re-form an S—S bond in the S-protected peptide, obtaining the cyclized peptide.
Dependencies are inferred from the claim text.