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Total Synthesis and Structural Characterization of Caveolin‐1
Author(s) -
Hojo Hironobu,
Takei Toshiki,
Asahina Yuya,
Okumura Nobuaki,
Takao Toshifumi,
So Masatomo,
Suetake Isao,
Sato Takeshi,
Kawamoto Akihiro,
Hirabayashi Yoshio
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202100826
Subject(s) - thioester , native chemical ligation , chemistry , peptide , palmitoylation , combinatorial chemistry , lipid bilayer , stereochemistry , model lipid bilayer , bilayer , sequence (biology) , side chain , peptide bond , biochemistry , chemical synthesis , cysteine , membrane , in vitro , organic chemistry , lipid bilayer phase behavior , enzyme , polymer
Abstract Caveolin‐1, which is an essential protein for caveola formation, was chemically synthesized. It is composed of 177 amino acid residues, is triply palmitoylated at the C‐terminal region, and is inserted into the lipid bilayer to form a V‐shaped structure in the middle of the polypeptide chain. The entire sequence was divided into five peptide segments, each of which was synthesized by the solid‐phase method. To improve the solubility of the C‐terminal region, O‐acyl isopeptide structures were incorporated. After ligation by the thioester method and the introduction of the palmitoyl groups, all the protecting groups were removed and the isopeptide structures were converted into the native peptide bond. Finally, the obtained polypeptide was successfully inserted into bicelles, thus showing the success of the synthesis.