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Fmoc-D-Sec(Xan)-OH
Chemical name: Fmoc-Se-xanthyl-D-selenocysteine // Synonyms: 2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(9H-xanthen-9-ylselanyl)-propionic acid, N-alpha-(9-Fluorenylmethyloxycarbonyl)-Se-xanthyl-D-selenocysteine, Fmoc-Sec(Xan)-OH
- Product code:FAA8600
- Formula:C31H25NO5Se
- Molecular weight:570.49 g/mol
- Purity :min. 98%
- Enantiomeric Purity:min. 99,9%
Starting at $202.50
description
The 21st proteinogenic amino acid Selenocysteine (Sec, U) plays a crucial role for several biological processes. Fmoc-Sec(Xan)-OH represents a Selenocysteine derivative suitable for Fmoc SPPS bearing Xanthenyl (Xan) as TFA-labile sidechain protecting group.
As reported for Fmoc-Cys(Xan)-OH, Xanthenyl removal is triggered by exposure to dilute TFA in the presence of silane or thiol scavengers: 0.1% TFA for 1 h or 0.2% TFA for 10 min is sufficient when silane scavengers are used (Et3SiH is slightly better than iPr3SiH); 10% TFA is needed in conjunction with b-mercaptoethanol.
Furthermore, in contrast to Fmoc-Sec(Trt)-OH the xanthyl derivative Fmoc-Sec(Xan)-OH is reported to be bench-stable at room temperature for extended timeframes (> 1 month).
See also FAA8465 Fmoc-L-Sec(Xan)-OH
references
Novel S-xanthenyl protecting groups for cysteine and their applications for the N-alpha-9 Fluorenylmethyloxycarbonyl (Fmoc) strategy of peptide synthesis; X. Han, G. Barany; J. Org. Chem. 1997; 62: 3841-3848. https://doi.org/10.1021/jo961882g.
Fmoc-Sec(Xan)-OH: Synthesis and Utility of Fmoc Selenocysteine SPPS Derivatives with Acid-Labile Sidechain Protection; S. Flemer Jr.; J. Pept. Sci. 2015; 21: 53-59. https://doi.org/10.1002/psc.2723.
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