N-alpha-(9-Fluorenylmethyloxycarbonyl)-3-(2-furyl)-L-alanine

2-Furyl-alanine has a set of surprising properties, which make it a useful tool for site-specific chemical modification of proteins, furan-mediated nucleic acid crosslinking and solid phase-based peptide labeling. It also already has been used in construction of fluorescent probes via peptide labeling and in antibody drug conjugates for diagnostic and therapeutic purposes. As an electron rich dien it can be used in Diels-Alder reaction with an appropriate dienophile. Photoactivation leads to singlet oxygen (1O2) mediated furan-based labeling, which can be carried out in physiological aqueous solutions. Hence, it is a powerful ligation tool for fast and efficient peptide, protein and antibody modification. References: Novel furan-oxidation based site-specific conjugation methodology for peptide labeling and antibody drug conjugates; presented at the 6th World ADC meeting October 19th-22nd 2015, San Diego, CA; An Van Den Bulcke, Eirini Antonatou, Willem Vannecke, Kurt Hoogewijs and Annemieke Madder; M. Sletten, C. R. Bertozzi, Angew. Chem. Int. Ed. 2009; 48: 6974. K. Stevens, A. Madder, Nucleic Acids Research 2009; 1555. M. Op De Beeck, A. Madder, J. Am. Chem. Soc. 2011; 133: 796. Op De Beeck, A. Madder, J. Am. Chem. Soc. 2012; 134: 10737. A. Deceuninck, A. Madder, Chem. Commun. 2009; 340. K. Hoogewijs, D. Buyst, J. M. Winne, J. C. Martins, A. Madder, Chem. Commun. 2013; 49: 2927. M. J. Schmidt, A. Weber, M. Pott, W. Welteand, D. Summerer, ChemBioChem 2014; 15: 1755. M. J. Schmidt, D. Summerer, Angew. Chem. Int. Ed. 2013; 52: 4690.