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Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-beta-anthraniloyl-L-alanine // Synonyms: (S)-2-(9-Fluorenylmethyloxycarbonylamino)-4-(2-aminophenyl)-4-oxobutanoic acid
|Molecular weight:||430,45 g/mol|
The non-proteinogenic amino acid Kynurenine (Kyn) is a known oxidation product of tryptophan. In cells, this process may be caused by reactive oxygen species (ROS). Such changes can lead to altered protein structure and function causing either degradation or accumulation/aggregation linked to the pathogenesis of several diseases. Our Fmoc-protected Kyn allows to synthesize model peptides for functional and structural studies.
Besides, Kyn is also part of Daptomycin (trade name Cubicin), an effective lipopeptide for the treatment of infections caused by antibiotic-resistant gram-positive pathogens.
A combined solid- and solution-phase approach provides convenient access to analogues of the calcium-dependent lipopeptide antibiotics; P. Hart, L. H. J. Kleijn, G. de Bruin, S. f. Oppedijk, J. Kemmink, and N. I. Martin; Org. Biomol. Chem. 2014; 12: 913-918. https://doi.org/10.1039/c3ob42238k.
Synthesis and Derivatization of Daptomycin: A Chemoenzymatic Route to Acidic Lipopeptide Antibiotics; J. Grünewald, S. A. Sieber, C. Mahlert, U. Linne, and M. A. Marahiel; J. Am. Chem. Soc. 2004; 126: 17025-17031. https://doi.org/10.1021/ja045455t.
Fluorescence Resonance Energy Transfer as a Probe of Peptide Cyclization Catalyzed by Nonribosomal Thioesterase Domains; J. Grünewald, F. Kopp, C. Mahlert, U. Linne, S. A. Sieber, M. A. Marahiel; Chem. Biol. 2005; 12: 873-881. https://doi.org/10.1016/j.chembiol.2005.05.019.
Synthesis of peptides containing 5‐hydroxytryptophan, oxindolylalanine, N‐formylkynurenine and kynurenine; T. Todorovski, M. Fedorova, L. Hennig, R. Hoffmann; J. Pept. Sci. 2011; 17: 256-262. https://doi.org/10.1002/psc.1322.
Mass spectrometric characterization of peptides containing different oxidized tryptophan residues; T. Todorovski, M. Fedorova, R. Hoffmann; J. Mass. Spectrom. 2011; 46: 1030-1038. https://doi.org/10.1002/jms.1984.
Total Synthesis of Laspartomycin C and Characterization of Its Antibacterial Mechanism of Action; L. H. J. Kleijn, S. F. Oppedijk, P. Hart, R. M. van Harten, L. A. Martin-Visscher, J. Kemmink, E. Breukink, and N. I. Martin; J. Med. Chem. 2016; 59: 3569-3574. https://doi.org/10.1021/acs.jmedchem.6b00219.
Establishing the Structure–Activity Relationship of Daptomycin; H. Y. Chow, K. H. L. Po, K. Jin, G Qiao, Z. Sun, W. Ma, X. Ye, N. Zhou, S. Chen, and X. Li; ACS Med. Chem. Lett. 2020; 11: 1442-1449. https://doi.org/10.1021/acsmedchemlett.0c00175.
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