Design and synthesis of a hydrogen peroxide-responsive amino acid that induces peptide bond cleavage after exposure to hydrogen peroxide. Issue 28 (8th July 2015)

• Record Type: Journal Article
• Authors: Kita, Miku; Yamamoto, Jun; Morisaki, Takuya; Komiya, Chiaki; Inokuma, Tsubasa; Miyamoto, Licht; Tsuchiya, Koichiro; Shigenaga, Akira; Otaka, Akira
• Is Part Of: Tetrahedron letters. Volume 56:Issue 28(2015)
• Page Start: 4228
• Page End: 4231
• Publication Date: 2015-07-08
• Subjects: Amide bond cleavage -- Hydrogen peroxide -- Oxidative stress -- Stimulus-responsive -- Trimethyl lock; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.05.060
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Oxidative stress-responsive compounds are attracting significant attention in the field of medicinal chemistry and chemical biology. Here, we disclose the development of a hydrogen peroxide (H2 O2 )-responsive amino acid that induces peptide bond cleavage in the presence of H2 O2 that closely relates to oxidative stress. The H2 O2 -responsive amino acid possessing a boronate or boronic acid moiety was incorporated into a peptide using Fmoc-based solid-phase peptide synthesis or that with minor modifications, respectively, and the peptide bond cleavage of the obtained peptide was successfully triggered by the addition of H2 O2 .