Thieme Chemistry Journal Awardees - Where are They Now? Scope of Tyrosine O-Arylations with Boronic Acids: Optimized Synthesis of an Orthogonally Protected Isodityrosine

Abstract

The Evans-Chan-Lam variant of the Ullman condensation has been explored to deliver O-arylated tyrosines and tyrosinyl peptides. Key modifications for success were the slow addition of boronic acids to the phenol-catalyst mixture. Selectivity and scope are investigated.

Key words

bioorganic chemistry - copper - cross coupling - peptides - phenols

References and Notes

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14

All peptides were accessed by standard solid-phase peptide synthesis protocols on 2-Cl-trityl or Rink-amide resins, when appropriate, using Fmoc-protected amino acids and HOBt, HBTU, and EtN(i-Pr)₂ as coupling reagents.