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Easy‐to‐Attach/Detach Solubilizing‐Tag‐Aided Chemical Synthesis of an Aggregative Capsid Protein
Author(s) -
Tsuda Shugo,
Mochizuki Masayoshi,
Ishiba Hiroyuki,
YoshizawaKumagaye Kumiko,
Nishio Hideki,
Oishi Shinya,
Yoshiya Taku
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201711546
Subject(s) - trifluoroacetic acid , chemistry , native chemical ligation , capsid , reagent , combinatorial chemistry , solubility , chromatography , thiol , chemical ligation , peptide , biochemistry , organic chemistry , chemical synthesis , in vitro , gene
Abstract A solubilizing Trt‐K 10 tag was developed for the effective chemical preparation of peptides/proteins with low solubility. The Trt‐K 10 tag comprises a hydrophilic oligo‐Lys sequence and a trityl anchor, and can be selectively introduced to a side chain thiol of Cys of deprotected peptides/proteins with a trityl alcohol‐type introducing reagent Trt(OH)‐K 10 under acidic conditions. Significantly, the ligation product in the reaction mixture of a thiol‐additive‐free native chemical ligation can be modified directly in a one‐pot manner to facilitate the isolation of the product by high‐performance liquid chromatography. Finally, the Trt‐K 10 tag can be readily removed with a standard trifluoroacetic acid cocktail. Using this easy‐to‐attach/detach tag‐aided method, a hepatitis B virus capsid protein that is usually difficult to handle was synthesized successfully.