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Fmoc-D-Sec(Xan)-OH
Nom chimique: Fmoc-Se-xanthyl-D-selenocysteine // Synonymes: 2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(9H-xanthen-9-ylselanyl)-propionic acid, N-alpha-(9-Fluorenylmethyloxycarbonyl)-Se-xanthyl-D-selenocysteine, Fmoc-Sec(Xan)-OH
- n° Art.:FAA8600
- n° CAS:2988660-46-2
- Formule:C31H25NO5Se
- Storage temperature:-20°C
- Masse moléculaire:570,49 g/mol
- Pureté:min. 98%
- Pureté Énantiomérique:min. 99,9%
from 162,00 €
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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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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