Synthesis of a selenocysteine-containing peptide by native chemical ligation

Org Lett. 2001 May 3;3(9):1331-4. doi: 10.1021/ol015712o.

Abstract

[reaction in text] A new method for the synthesis of selenocysteine derivatives and selenocysteine-containing peptides is described. Fmoc-Se-p-methoxybenzylselenocysteine (1) was prepared and used for solid-phase synthesis of peptides with an N-terminal unprotected selenocysteine. Subsequent native chemical ligation with a peptide thioester provided a 17-mer that corresponds to the C-terminus of ribonucleotide reductase with selenocysteine in place of cysteine.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Ribonucleotide Reductases / chemistry
  • Selenocysteine / chemical synthesis*
  • Selenocysteine / chemistry
  • Sequence Analysis, Protein
  • Sequence Homology, Amino Acid
  • Structure-Activity Relationship

Substances

  • Peptides
  • Selenocysteine
  • Ribonucleotide Reductases