A convenient synthesis of new chromophoric tetracyanobutadiene-scaffolded peptides via a dipolar [2+2] cycloaddition-cycloreversion reaction

作者：Rijkers Dirk T S^*; Diederich Francois

来源：Tetrahedron Letters, 2011, 52(31): 4021-4025.

DOI：10.1016/j.tetlet.2011.05.136

• Acetylenes
• Cycloaddition
• Donor-acceptor chromophores
• pi-Conjugated peptides
• Peptides
• Peptidomimetics

Herein, we report a novel approach for the synthesis of it-conjugated peptide-based donor-acceptor (D-pi-A) chromophores, by reacting electron-rich alkynes with tetracyanoethylene. The desired tetracy-anobutadiene-scaffolded peptides were obtained in good yields with various optical properties, lambda(max): 321-492 nm, epsilon: 21,000-65,000 mol(-1) dm(3) cm(-1) depending on the substitution pattern of the cyanobutadiene scaffold.

• 出版日期2011-8-3