Development of caged non-hydrolyzable phosphoamino acids and application to photo-control of binding affinity of phosphopeptide mimetic to phosphopeptide-recognizing protein

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• 作者：Koji Ebisuno ; Masaya Denda ; Keiji Ogura ; Tsubasa Inokuma ; Akira Shigenaga ; ^{shigenaga.akira@tokushima-u.ac.jp" class="auth_mail} ; Akira Otaka ; ^{aotaka@tokushima-u.ac.jp" class="auth_mail}
• 关键词：Caged peptide ; Non-hydrolyzable ; Phosphoamino acid ; Phosphopeptide ; UV-responsive
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：1 June 2014
• 年：2014
• 卷：22
• 期：11
• 页码：2984-2991
• 全文大小：1003 K

文摘

The design and synthesis of caged non-hydrolyzable phospho-serine, -threonine, and -tyrosine derivatives that generate parent non-hydrolyzable phosphoamino acids, containing a difluoromethylene unit instead of the oxygen of a phosphoester, after UV-irradiation are described. The caged non-hydrolyzable amino acids were incorporated into peptides by standard Fmoc solid-phase peptide synthesis, and the obtained peptides were successfully converted to the parent non-hydrolyzable phosphopeptides by UV-irradiation. Application of the caged non-hydrolyzable phosphoserine-containing peptide to photo-control the binding affinity of the peptide to 14-3-3尾 protein is also reported.