N-alpha-(9-Fluorenylmethyloxycarbonyl)-beta,beta-dimethyl-(2-methyl-6-(2-nitrobenzyloxy)phenyl)alanine (rac.)

This stimulus-responsive peptide-bond-cleaving residue (Spr) is an amino acid based on the trimethyl-lock concept. Biologically active peptides or other compounds can be masked and specifically be activate by a stimulus. By photolysis at 365nm within 3 min the active part of the peptide can be triggered in a traceless release. A wide range of applications already has been published, like prodrug and drug release, use as self immolative spacer or in biomolecular imaging, cleavage and release of peptides and proteins. References: FRET-based assay of the processing reaction kinetics of stimulus-responsive peptides: influence of amino acid sequence on reaction kinetics; Akira Shigenaga, Jun Yamamoto, Hiroko Hirakawa, Keiko Yamaguchi, Akira Otaka; Tetrahedron 2009; 65: 2212-2216. DOI: 10.1016/j.tet.2009.01.063 Enantioselective synthesis of stimulus-responsive amino acid via asymmetric a-amination of aldehyde; Akira Shigenaga, Jun Yamamoto, Naomi Nishioka, Akira Otaka; Tetrahedron 2010; 66: 7367e7372. DOI: 10.1016/j.tet.2010.07.033 Design and synthesis of caged ceramide: UV-responsive ceramide releasing system based on UV-induced amide bond cleavage followed by O-N acyl transfer; Akira Shigenaga, Hiroko Hirakawa, Jun Yamamoto, Keiji Ogura, Masaya Denda, Keiko Yamaguchi, Daisuke Tsuji, Kohji Itoh, Akira Otaka; Tetrahedron 2011; 67: 3984-3990. DOI: 10.1016/j.tet.2011.04.048 Development and photo-responsive peptide bond cleavage reaction of two-photon near-infrared excitation-responsive peptide; Akira Shigenaga, Jun Yamamoto, Yoshitake Sumikawa, Toshiaki Furuta, Akira Otaka; Tet. Lett. 2010; 51: 2868-2871. DOI: 10.1016/j.tetlet.2010.03.079 Photo-triggered fluorescent labelling of recombinant proteins in live cells; Deokho Jung, Kohei Sato, Kyoungmi Min, Akira Shigenaga, Juyeon Jung, Akira Otaka, and Youngeun Kwon; Chem. Commun. 2015: 51: 9670-9673. DOI: 10.1039/c5cc01067e Invention of stimulus-responsive peptide-bond-cleaving residue (Spr) and its application to chemical biology tools; Akira Shigenaga, Jun Yamamoto, Taiki Kohiki, Tsubasa Inokuma, and Akira Otaka; J. Pept. Sci. 2017; 23: 505-513. DOI: 10.1002/psc.2961