A convenient [2+2] cycloaddition-cycloreversion reaction for the synthesis of 1,1-dicyanobuta-1,3-diene-scaffolded peptides as new imaging chromophores期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

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A convenient [2+2] cycloaddition-cycloreversion reaction for the synthesis of 1,1-dicyanobuta-1,3-diene-scaffolded peptides as new imaging chromophores

Authors:	Dirk TS Rijkers Fernando de Prada LópezRob MJ Liskamp François Diederich

Institution:	^a Medicinal Chemistry & Chemical Biology, Utrecht Institute for Pharmaceutical Sciences, Department of Pharmaceutical Sciences, Faculty of Science, Utrecht University, Universiteitsweg 99, 3584 CG Utrecht, The Netherlands ^b Laboratorium für Organische Chemie, ETH-Zürich, Hönggerberg HCI, Wolfgang-Pauli-Strasse 10, CH-8093 Zürich, Switzerland

Abstract:	We report on the chemoselective coupling between colorless peptide fragments functionalized with a mutually reactive electron-rich N^α-(4-ethynylphenyl)-N^α-(methyl)-glycyl- and an electron-deficient 4-(2,2-dicyanovinyl)]benzoyl moiety. The resulting donor-substituted 1,1-dicyanobuta-1,3-dienes represent a new class of orange-red colored (λ_max = 450-500 nm, with molar extinction coefficients (ε) above 5,000 mol⁻¹ dm³ cm⁻¹) peptide-based imaging chromophores.

Keywords:	Cycloaddition Dicyanovinyl derivatives Donor-acceptor chromophores π-Conjugated peptides Peptides Peptidomimetics
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