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Fmoc-L-Tyr(SO3DCV)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-O-(dichlorovinyl-sulfo)-L-tyrosine // Synonyms: (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-((((2,2-dichlorovinyl)oxy)sulfonyl)oxy)phenyl)propanoic acid, Fmoc-Tyr(SO3DCV)-OH,O-[[(2,2-dichloroethenyl)oxy]sulfonyl]-N-[(9H-fluoren-9-ylmet hoxy)carbonyl]-L-Tyrosine
- Product code:FAA8485
- CAS No.:1151854-06-6
- Formula:C26H21Cl2NO8S
- Molecular weight:578.41 g/mol
- Purity :min. 98%
Starting at $383.50
description
A derivative for the synthesis of sulfotyrosine-containing peptides by Fmoc-SPPS. Tyrosine sulfation is a post translational modification that occurs on integral membrane and secreted proteins, and plays a crucial role in mediating biological processes. Thus, this derivative is useful for the study of site-specific tyrosine sulfation and its effect on peptide stability and activity. The sulfate group of FAA8485 is protected with a dichlorovinyl (DCV) group. After synthesis, the peptide is cleaved from the resin using TFA/TIS and all side chain protective groups except DCV are removed. The DCV group is removed at the end of the synthesis by hydrogenolysis using Pd/C, H2 and ammonium formate.
references
Synthesis of disulfated peptides corresponding to the N-terminus of chemokines receptors CXCR6 (CXCR6 1-20) and DARC (DARC 8-42) using a sulfate-protecting group strategy; A. M. Ali, S. D. Taylor; J. Pept. Sci. 2010; 16(4): 190-199. https://doi.org/10.1002/psc.1220.
Efficient solid-phase synthesis of sulfotyrosine peptides using a sulfate protecting-group strategy; A. M. Ali, S. D. Taylor; Angew. Chem. Int. Ed. Engl. 2009; 48(11): 2024-6. https://doi.org/10.1002/anie.200805642.
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