Methionine anchoring applied to the solid-phase synthesis of lysine-containing 'head-to-tail' cyclic peptides

Joseph C. Kappel, George Barany

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

Lysine-containing 'head-to-tail' cyclic peptides can be prepared via a side-chain anchoring solid-phase synthesis strategy. A handle is prepared using a methionine residue, the Cα-carboxyl of which forms an amide with the Nε-amine of lysine. Subsequently, the linear peptide sequence is assembled, appropriate deblocking steps are carried out, and on-resin head-to-tail cyclization follows. Optionally, acid-labile protecting groups may be removed while the peptide remains resin-bound. The final cleavage step uses CNBr, and releases the free or protected cyclic peptide into solution.

Original languageEnglish (US)
Pages (from-to)119-125
Number of pages7
JournalLetters in Peptide Science
Volume10
Issue number2
DOIs
StatePublished - Dec 1 2003

Keywords

  • Cyanogen bromide
  • Cyclic peptides
  • Lysine attachment
  • Methionine linker
  • Orthogonal protection
  • Side-chain anchoring
  • Solid-phase synthesis

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