Sortase A-catalyzed peptide cyclization for the synthesis of macrocyclic peptides and glycopeptides

Chem Commun (Camb). 2011 Aug 28;47(32):9218-20. doi: 10.1039/c1cc13322e. Epub 2011 Jul 8.

Abstract

A chemoenzymatic method was developed for the synthesis of macrocyclic peptides and glycopeptides. Sortase A was found to mediate either head to tail cyclization or oligomerization and then head to tail cyclization of peptides and glycopeptides, depending on the peptide length, to produce 15-mer or higher cyclic peptides and glycopeptides.

Publication types

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

MeSH terms

  • Amino Acid Sequence
  • Aminoacyltransferases / metabolism*
  • Bacterial Proteins / metabolism*
  • Cyclization
  • Cysteine Endopeptidases / metabolism*
  • Glycopeptides / chemical synthesis*
  • Glycopeptides / metabolism
  • Gram-Positive Bacteria / enzymology*
  • Molecular Sequence Data
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / metabolism

Substances

  • Bacterial Proteins
  • Glycopeptides
  • Peptides, Cyclic
  • Aminoacyltransferases
  • sortase A
  • Cysteine Endopeptidases