Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-beta,beta-dimethyl-(2,4-dimethyl-6-(2-nitrobenzyloxy)phenyl)alanine (rac.) // Synonyms: (R,S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-methyl-3-(2,4-dimethyl-6-(2-nitrobenzyloxy)phenyl)butanoic acid, Fmoc-Trimethyl-Lock-Phe(oNBzl)-OH

  • Product code:FAA7190
  • CAS No.:1032400-98-8
  • Formula:C35H34N2O7
  • Molecular weight:594.66 g/mol

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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.


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

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