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Fmoc-L-His(2-Thio)-OH
Chemical name: (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(2-thioxo-2,3-dihydro-1H-imidazol-4-yl)propanoic acid // Synonyms: Fmoc-2-Thio-L-Histidine, Fmoc-His(2-Thio)-OH
- Product code:FAA8810
- CAS No.:2851463-63-1
- Formula:C21H19N3O4S
- Molecular weight:409.46 g/mol
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description
An analogue of ergothioneine, which can be incorporated into peptides to increase the antioxidant capacity of the peptide.
references
Short protecting-group-free synthesis of 5-acetylsulfanyl-histidines in water: novel precursors of 5-sulfanyl-histidine and its analogues; Org. Biomol. Chem. 2016; 14: 10473-10480. https://doi.org/10.1039/C6OB01870J.
Improved synthesis of the super antioxidant, ergothioneine, and its biosynthetic pathway intermediates; P. L. Khonde, A. Jardine; Org. Biomol. Chem. 2015; 13: 1415-1419. https://doi.org/10.1039/C4OB02023E.
Cysteine as a suitable sulfur reagent for the protecting-group-free synthesis of sulfur-containing amino acids: biomimetic synthesis of L-ergothioneine in water; I. Erdelmeier, S. Daunay, R. Lebel, L. Farescour, J.-C. Yadan; Green Chem. 2012; 14: 2256-2265. https://doi.org/10.1039/C2GC35367A.
Role of 2-oxo and 2-thioxo modifications on the fragmentation reactions of histidine radical cation; Rapid Commun. Mass Spectrom. 2011; 25: 251-261.
Ergothioneine in a peptide: Substitution of histidine with 2-thiohistidine in bioactive peptides: K. A. Jenny, E. L. Ruggles, M. D. Liptak, D. S. Masterson, R. J. Hondal; J. Pept. Sci. 2021; 27(10): e3339.
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