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Fmoc-L-His(2-Oxo)-OH
Chemical name: (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(2-oxo-2,3-dihydro-1H-imidazol-4-yl)propanoic acid // Synonyms: Fmoc-2-Oxo-Histidine, Oxohistidine, Fmoc-2-Oxo-L-Histidine, Fmoc-2-Oxo-Histidine, Fmoc-2-Oxohistidine, Fmoc-His(2-Oxo)-OH
- Product code:FAA8800
- CAS No.:2679858-41-2
- Formula:C21H19N3O5
- Storage temperature:-20°C
- Molecular weight:393.40 g/mol
from €1,000.00
description
Histidine is one of the major oxidation targets due to its metal‐chelating property and susceptibility to metal‐catalyzed oxidation. The major product of histidine oxidation, 2-oxohistidine, has been identified as a stable marker of oxidative damage in biological system, associated with aging and neurodegenerative disorders. Peptide probes and peptide antigens containing 2‐oxohistidine will help to advance the study of non‐enzymatic posttranslational modification.
references
Synthesis of peptides containing 2-oxohistidine residues and their characterization by liquid chromatography-tandem mass spectrometry; C.-F. Huang, Y.-H. Liu, H.-C. Tai; J. Pept. Sci. 2014; 21(2): 114-119. https://doi.org/10.1002/psc.2735.
Role of 2-oxo and 2-thioxo modifications on the fragmentation reactions of histidine radical cation; Rapid Commun. Mass Spectrom. 2011; 25: 251-261.
Model Studies on the Metal-Catalyzed Protein Oxidation: Structure of a Possible His-Lys Cross-Link; Y. Liu, G. Sun, A. David, L. M. Sayre; Chem. Res. Toxicol. 2004; 17(1): 110-118. https://doi.org/10.1021/tx034167s.
Determination of 2-Oxohistidine by Amino Acid Analysis; S. A. Lewisch, R. L. Levine; Anal. Biochem. 1995; 231: 440-446. https://doi.org/10.1006/abio.1995.9974.
Identification of oxidized histidine generated at the active site of Cu,Zn-superoxide dismutase exposed to H2O2. Selective generation of 2-oxo-histidine at the histidine 18. K. Uchida, S. Kawakishi; J. Biol. Chem. 1994; 269(4): 2405-2410. https://doi.org/10.1016/S0021-9258(17)41960-0.
2-Oxo-histidine as a novel biological marker for oxidatively modified proteins; K. Uchida, S. Kawakishi; FEBS Lett. 1993; 332(3): 208-210. https://doi.org/10.1016/0014-5793(93)80632-5.
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