Arylation of Phe and Tyr side chains of unprotected peptides by a Suzuki-Miyaura reaction in water

Org Lett. 2008 Aug 7;10(15):3243-5. doi: 10.1021/ol801009z. Epub 2008 Jul 4.

Abstract

An efficient arylation in water of tyrosine and phenylalanine side chains from unprotected iodopeptides is accomplished by using Suzuki-Miyaura cross-coupling processes. The method is compatible with the hydrophilic and thermolabile nature of biologically active peptides. Also of interest, the arylated tyrosine peptides can be accessed in one-pot mode starting from native peptides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Enkephalin, Leucine / chemistry
  • Iodoproteins / chemistry*
  • Onium Compounds / chemistry
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Phenylalanine / chemistry*
  • Pyridines / chemistry
  • Tyrosine / chemistry*

Substances

  • Iodoproteins
  • Onium Compounds
  • Peptides
  • Pyridines
  • bis(pyridine)iodonium(I) tetrafluoroborate
  • Tyrosine
  • Phenylalanine
  • Enkephalin, Leucine