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Synthesis of Sulfotyrosine‐Containing Peptides by Incorporating Fluorosulfated Tyrosine Using an Fmoc‐Based Solid‐Phase Strategy
Author(s) -
Chen Wentao,
Dong Jiajia,
Li Suhua,
Liu Yu,
Wang Yujia,
Yoon Leonard,
Wu Peng,
Sharpless K. Barry,
Kelly Jeffery W.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201509016
Subject(s) - tyrosine , chemistry , solid phase synthesis , peptide , residue (chemistry) , peptide synthesis , combinatorial chemistry , ethylene glycol , amino acid , side chain , sulfation , stereochemistry , biochemistry , organic chemistry , polymer
Tyrosine O‐sulfation is a common protein post‐translational modification that regulates many biological processes, including leukocyte adhesion and chemotaxis. Many peptides with therapeutic potential contain one or more sulfotyrosine residues. We report a one‐step synthesis for Fmoc‐fluorosulfated tyrosine. An efficient Fmoc‐based solid‐phase peptide synthetic strategy is then introduced for incorporating the fluorosulfated tyrosine residue into peptides of interest. Standard simultaneous peptide‐resin cleavage and removal of the acid‐labile side‐chain protecting groups affords the crude peptides containing fluorosulfated tyrosine. Basic ethylene glycol, serving both as solvent and reactant, transforms the fluorosulfated tyrosine peptides into sulfotyrosine peptides in high yield.