Synthesis of Sulfotyrosine-Containing Peptides by Incorporating Fluorosulfated Tyrosine Using an Fmoc-Based Solid-Phase Strategy

Wentao Chen, Jiajia Dong, Suhua Li, Yu Liu, Yujia Wang, Leonard Yoon, Peng Wu, K. Barry Sharpless, Jeffery W. Kelly

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)1835-1838
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number5
DOIs
StatePublished - Jan 26 2016
Externally publishedYes

Fingerprint

Peptides
Tyrosine
Ethylene Glycol
tyrosine O-sulfate
Ethylene glycol
Adhesion
Resins
Proteins
Acids

Keywords

  • click chemistry
  • peptides
  • solid-phase synthesis
  • SuFEx
  • sulfotyrosine

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Synthesis of Sulfotyrosine-Containing Peptides by Incorporating Fluorosulfated Tyrosine Using an Fmoc-Based Solid-Phase Strategy. / Chen, Wentao; Dong, Jiajia; Li, Suhua; Liu, Yu; Wang, Yujia; Yoon, Leonard; Wu, Peng; Sharpless, K. Barry; Kelly, Jeffery W.

In: Angewandte Chemie - International Edition, Vol. 55, No. 5, 26.01.2016, p. 1835-1838.

Research output: Contribution to journalArticle

Chen, Wentao ; Dong, Jiajia ; Li, Suhua ; Liu, Yu ; Wang, Yujia ; Yoon, Leonard ; Wu, Peng ; Sharpless, K. Barry ; Kelly, Jeffery W. / Synthesis of Sulfotyrosine-Containing Peptides by Incorporating Fluorosulfated Tyrosine Using an Fmoc-Based Solid-Phase Strategy. In: Angewandte Chemie - International Edition. 2016 ; Vol. 55, No. 5. pp. 1835-1838.
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AU - Liu, Yu

AU - Wang, Yujia

AU - Yoon, Leonard

AU - Wu, Peng

AU - Sharpless, K. Barry

AU - Kelly, Jeffery W.

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