Title:
CYCLIC PEPTIDE COMPOUND SIMULATING NATURAL PRODUCT STRUCTURE, AND METHOD FOR PREPARATION THEREOF
Document Type and Number:
WIPO Patent Application WO/2020/228097
Kind Code:
A1
Abstract:
Provided are a cyclic peptide compound simulating a natural product structure, and a method for preparation thereof. The preparation method is: the compound of formula I, a divalent palladium catalyst, and a silver salt undergoing an intramolecular arylation reaction in a solvent under heating and stirring to construct a cyclic peptide, to generate the compound of formula II. In the prepared cyclic peptide compound, the arylation sites are diverse, and can be extended to the side chain γ-position methyl or methylene of the majority of hydrophobic amino acids (amino acids connected to the PA at the N-terminus) to perform intramolecular arylation to construct a cyclic peptide, thus overcoming the defect of the limitation of the original types of selectable amino acids, and effectively constructing a novel aromatic ring-supported cyclic peptide compound. The aromatic ring support structure of this type of cyclic peptide can be fully integrated into the backbone of the cyclic peptide molecule, forming a novel 3D structure similar to a natural product, and providing a very favorable support for the subsequent construction of a cyclic peptide molecular library and high-throughput drug screening.
Inventors:
CHEN GONG (CN)
LI BO (CN)
LI XINGHUA (CN)
HAN BOYANG (CN)
HE GANG (CN)
LI BO (CN)
LI XINGHUA (CN)
HAN BOYANG (CN)
HE GANG (CN)
Application Number:
PCT/CN2019/092373
Publication Date:
November 19, 2020
Filing Date:
June 21, 2019
Export Citation:
Assignee:
UNIV NANKAI (CN)
International Classes:
C07K5/083; C07K1/02; C07K5/087; C07K5/103; C07K5/107; C07K7/06
Foreign References:
| CN106995483A | 2017-08-01 |
Other References:
ZHANG, X. K. ET AL.: "A general strategy for synthesis of cyclophane-braced peptide macrocycles via palladium-catalysed intramolecular sp3 C-H arylation", NATURE CHEMISTRY, vol. 10, 2 April 2018 (2018-04-02), XP036928977, DOI: 20200119173810
NOISIER, A. F. M. ET AL.: "C-H Functionalization in the Synthesis of Amino Acids and Peptides", CHEMICAL REVIEWS, vol. 114, 21 August 2014 (2014-08-21), XP55752914, DOI: 20200119174012A
HE, G. ET AL.: "Syntheses and Transformations of α-Amino Acids via Palladium-Catalyzed Auxiliary-Directed sp3 C−H Functionalization", ACC. CHEM. RES., vol. 49, 25 March 2016 (2016-03-25), XP55752917, DOI: 20200119174417A
HE, G. ET AL.: "Total Synthesis of Hibispeptin A via Pd-Catalyzed C(sp3)−H Arylation with Sterically Hindered Aryl Iodides", ORG. LETT., vol. 16, 9 December 2014 (2014-12-09), XP55752919, DOI: 20200119174905A
NOISIER, A. F. M. ET AL.: "C-H Functionalization in the Synthesis of Amino Acids and Peptides", CHEMICAL REVIEWS, vol. 114, 21 August 2014 (2014-08-21), XP55752914, DOI: 20200119174012A
HE, G. ET AL.: "Syntheses and Transformations of α-Amino Acids via Palladium-Catalyzed Auxiliary-Directed sp3 C−H Functionalization", ACC. CHEM. RES., vol. 49, 25 March 2016 (2016-03-25), XP55752917, DOI: 20200119174417A
HE, G. ET AL.: "Total Synthesis of Hibispeptin A via Pd-Catalyzed C(sp3)−H Arylation with Sterically Hindered Aryl Iodides", ORG. LETT., vol. 16, 9 December 2014 (2014-12-09), XP55752919, DOI: 20200119174905A
Attorney, Agent or Firm:
SBZL IP LAW OFFICE (CN)
Download PDF: