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Solubilizing Trityl‐Type Tag To Synthesize Asx/Glx‐Containing Peptides
Author(s) -
Tsuda Shugo,
Masuda Shun,
Yoshiya Taku
Publication year - 2019
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201900193
Subject(s) - chemistry , biochemistry , combinatorial chemistry
A novel solubilizing tag system for Asp/Asn/Glu/Gln‐containing peptides is described. In this method, an Asp/Glu[Dbz‐Cys‐NH 2 ]‐containing peptide (Dbz: 3,4‐diaminobenzoic acid) is first synthesized through fluorenylmethyloxycarbonyl (Fmoc) solid‐phase peptide synthesis. The solubilizing moiety containing an oligo‐Lys group is then attached to the peptide in hexafluoroisopropanol through a trityl anchor to afford a hydrophilic tagged peptide. To detach the solubilizing tag, the Dbz moiety of the tagged peptide is activated with NaNO 2 , and the Asp/Asn/Glu/Gln‐containing peptide is obtained through hydrolysis or ammonolysis. This synthetic approach proved to be compatible with native chemical ligation, and amyloid β‐protein 1–42 was successfully synthesized by the solubilizing‐tag‐aided native chemical ligation–desulfurization method.