Beta-replacement reaction of serine-O-carbonate derivatives with thiols catalyzed by a pyridoxal model having an ionophore side-chain

Chem Commun (Camb). 2002 Sep 7:(17):1922-3. doi: 10.1039/b206061b.

Abstract

Serine-O-carbonate derivatives, including peptides having a serine-O-carbonate residue at the N-terminal position, are catalytically transformed into S-substituted cysteine derivatives employing the pyridoxal model having an ionophore function in the presence of Li+; this is the first artificial model mimicking cystathionine Beta-synthase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbonates / chemistry*
  • Catalysis
  • Cystathionine beta-Synthase / metabolism
  • Cysteine / chemistry
  • Ionophores / chemistry*
  • Lithium
  • Molecular Structure
  • Peptides / chemistry
  • Pyridoxal / chemistry*
  • Serine / analogs & derivatives*
  • Serine / chemistry*
  • Sulfhydryl Compounds / chemistry*

Substances

  • Carbonates
  • Ionophores
  • Peptides
  • Sulfhydryl Compounds
  • Pyridoxal
  • Serine
  • Lithium
  • Cystathionine beta-Synthase
  • Cysteine