Fmoc-Spr(oNB)-OH

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
Grouped product items
Qty Packing unit Price SKU
100 mg
$506.25
FAA7190.0100
250 mg
$1,147.50
FAA7190.0250
1 g
$3,375.00
FAA7190.0001
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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