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Fmoc-D-Kyn(CHO)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-beta-anthraniloyl-(2-formamido)-D-alanine // Synonyms: (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(2-formamidophenyl)-4-oxobutanoic acid, Fmoc-Kyn(CHO)-OH, Fmoc-D-Kynurenine(CHO)-OH
- Product code:FAA8785
- Formula:C26H22N2O6
- Storage temperature:2-8°C
- Molecular weight:458.47 g/mol
from $1,062.50
description
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.
references
Effective synthesis of kynurenine-containing peptides via on-resin ozonolysis of tryptophan residues: synthesis of cyclomontanin B; C. T. T. Wong, H. Y. Lam, X. Li; Org. Biomol. Chem. 2013; 11: 7616-7620. https://doi.org/10.1039/C3OB41631C.
Total Synthesis of Daptomycin by Cyclization via Chemoselective Serine Ligation; H. Y. Lam, Y. Zhang, H. Liu, J. Xu, C. T. T. Wong, C. Xu, X. Li; J. Am. Chem. Soc. 2013; 135(16): 6272-6270. https://doi.org/10.1021/ja4012468.
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.
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