US 11,939,404 B2
Method for producing cyclized peptide having intramolecular S-S bond
Daisuke Takahashi, Kawasaki (JP); Tatsuji Inomata, Yokkaichi (JP); and Yuki Shinohara, Yokkaichi (JP)
Assigned to AJINOMOTO CO., INC., Tokyo (JP)
Filed by AJINOMOTO CO., INC., Tokyo (JP)
Filed on May 13, 2021, as Appl. No. 17/319,346.
Application 17/319,346 is a continuation of application No. PCT/JP2019/044962, filed on Nov. 15, 2019.
Claims priority of application No. 2018-216024 (JP), filed on Nov. 16, 2018.
Prior Publication US 2021/0277063 A1, Sep. 9, 2021
Int. Cl. C07K 7/64 (2006.01); C07K 1/06 (2006.01); C07K 1/107 (2006.01)
CPC C07K 7/64 (2013.01) [C07K 1/061 (2013.01); C07K 1/107 (2013.01)] 31 Claims
 
1. 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.