Synthesis and biological evaluation of the disulfide form of the glutathione analogue gamma-(L-glutamyl)-L-cysteinyl-L-aspartyl-L-cysteine

Bioorg Chem. 2003 Apr;31(2):109-21. doi: 10.1016/s0045-2068(03)00022-1.

Abstract

By using the chain to chain mode of cyclization the title glutathione analogue (4), containing the 11-membered disulfide ring replacing the native -Cys-Gly fragment, has been synthesized and characterized together with its reduced dithiol form gamma-Glu-Cys-Asp-Cys (5). The activity of (4) with gamma-glutamyl-transferase and glutathione reductase has been evaluated and compared with those of the two conformationally restricted glutathione analogues (2) and (3) previously reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cattle
  • Disulfides / chemistry*
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Glutathione / analogs & derivatives*
  • Glutathione / chemical synthesis
  • Glutathione / pharmacology
  • Glutathione Reductase / antagonists & inhibitors
  • Kidney / enzymology
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacology
  • Saccharomyces cerevisiae / enzymology
  • Structure-Activity Relationship
  • Swine
  • gamma-Glutamyltransferase / antagonists & inhibitors

Substances

  • Disulfides
  • Enzyme Inhibitors
  • Oligopeptides
  • gamma-glutamyl-cysteinyl-aspartyl-cysteine
  • Glutathione Reductase
  • gamma-Glutamyltransferase
  • Glutathione