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Fmoc-L-Tyr(SO3nP)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-O-(2,2-dimethylpropylsulfo)-L-tyrosine // Synonyms: (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-(((neopentyloxy)sulfonyl)oxy)phenyl)propanoic acid,O-[(2,2-dimethylpropoxy)sulfonyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-Tyrosine, Fmoc-Tyr( SO3nP)-OH
- Product code:FAA8490
- CAS No.:878408-63-0
- Storage temperature:-20°C
- Formula:C29H31NO8S
- Molecular weight:553.63 g/mol
from €330.00
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 neopentyl (nP) group, which is stable to TFA. Neopentyl groups can be removed by treatment with aqueous ammonium acetate (1-2 M, 37 °C water bath, 6-12 hrs) or sodiumazide (50 eq, 70 °C, 16 h).
references
Regulation of chemokine recognition by site-specific tyrosine sulfation of receptor peptides; L. S. Simpson, J. Z. Zhu, T. S. Widlanski, M. J. Stone; Chem. Biol. 2009; 16(2): 153-61. https://doi.org/10.1016/j.chembiol.2008.12.007.
Phosphate modulates receptor sulfotyrosine recognition by the chemokine monocyte chemoattractant protein-1 (MCP-1/CCL2). J. P. Ludeman, M. Nazari-Robati, B. L. Wilkinson, C. Huang, R. J. Payne, M. J. Stone; Org. Biomol. Chem. 2015; 13, 2162-2169. https://doi.org/10.1039/C4OB02262A.
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