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

Rijkers, D.T.S., de Prada López, F., Liskamp, R.M.J. and Diederich, F. (2011) A convenient [2+2] cycloaddition–cycloreversion reaction for the synthesis of 1,1-dicyanobuta-1,3-diene-scaffolded peptides as new imaging chromophores. Tetrahedron Letters, 52(51), pp. 6963-6967. (doi: 10.1016/j.tetlet.2011.10.084)

Abstract

We report on the chemoselective coupling between colorless peptide fragments functionalized with a mutually reactive electron-rich Nα-(4-ethynylphenyl)-Nα-(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 (λmax = 450–500 nm, with molar extinction coefficients (ε) above 5,000 mol−1 dm3 cm−1) peptide-based imaging chromophores.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Liskamp, Professor Robert
• Authors: Rijkers, D.T.S., de Prada López, F., Liskamp, R.M.J., and Diederich, F.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Tetrahedron Letters
• ISSN: 0040-4039
• ISSN (Online): 1873-3581