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Fmoc-Spr(oNv)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-beta,beta-dimethyl-(2-methyl-6-(2-nitroveratryl)phenyl)alanine (rac.) // Synonyms: (R,S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(2-(4,5-dimethoxy-2-nitrobenzyloxy)-6-methylphenyl)-3-methylbutanoic acid, Fmoc-Trimethyl-Lock-Phe(oNv)-OH
- Product code:FAA7200
- CAS No.:1228829-20-6
- Formula:C36H36N2O9
- Molecular weight:640.68 g/mol
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description
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
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