US 12,466,850 B2
Method for producing peptide compound
Akihiro Nagaya, Funabashi (JP); Michiharu Handa, Funabashi (JP); and Yuji Mimori, Funabashi (JP)
Assigned to NISSAN CHEMICAL CORPORATION, Tokyo (JP)
Appl. No. 17/639,217
Filed by NISSAN CHEMICAL CORPORATION, Tokyo (JP)
PCT Filed Aug. 27, 2020, PCT No. PCT/JP2020/032343
§ 371(c)(1), (2) Date Feb. 28, 2022,
PCT Pub. No. WO2021/039901, PCT Pub. Date Mar. 4, 2021.
Claims priority of application No. 2019-158350 (JP), filed on Aug. 30, 2019.
Prior Publication US 2022/0306682 A1, Sep. 29, 2022
Int. Cl. C07K 1/06 (2006.01); C07F 7/08 (2006.01)
CPC C07K 1/062 (2013.01) [C07F 7/081 (2013.01)] 36 Claims
 
1. A method for producing a peptide, comprising the steps of:
(1) removing the N-terminal protective group of an amino acid or peptide compound represented by the following formula (I):

OG Complex Work Unit Chemistry
wherein
Y represents a residue of an N-protected amino acid or an N-protected peptide, and
each of R1, R2, and R3 independently represents an aliphatic hydrocarbon group which may have a substituent in which each of 1 to 5 methylene groups in the aliphatic hydrocarbon group may be independently replaced by a structure selected from the group consisting of —O—, —CO—, —N(R6)—, —N(R7)CO—, and —CON(R8)— or an aromatic hydrocarbon group which may have a substituent, wherein each of R6, R7, and R8 independently represents a hydrogen atom or a C1-6 alkyl group,
wherein at least one of the R1, R2, and R3 is an aliphatic hydrocarbon group which may have a substituent in which one methylene group in the aliphatic hydrocarbon group may be replaced by —O—, and 3 or more carbon atoms in the aliphatic hydrocarbon group are tertiary or quaternary carbon atoms;
wherein the total number of carbon atoms in the R1R2R3Si group is 18 to 80, and the R1R2R3SiCH2CH2 group is bonded to the C-terminus of the amino acid or peptide residue in Y;
and
(2) causing condensation of an N-protected amino acid or an N-protected peptide and the N-terminus of the C-protected amino acid or C-protected peptide obtained in the step (1).