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Boc-L-Kyn-OH
Chemical name: N-alpha-(t-Butyloxycarbonyl)-beta-anthraniloyl-L-alanine // Synonyms: (S)-4-(2-aminophenyl)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid, Boc-Kynurenine, Boc-L-Kynurenine-OH, Boc-Kyn-OH
- Product code:BAA4820
- CAS No.:74802-08-7
- Formula:C15H20N2O5
- Storage temperature:2-8°C
- Molecular weight:308.33 g/mol
from $937.50
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
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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All information contained in our webshop is compiled to the best of our knowledge.
Prices and product availability are subject to change and require reconfirmation. Please contact us for further information.
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