title: Chemoselective Protection of Glutathione in the Preparation of Bioconjugates: The Case of Trypanothione Disulfide.
abstract: A novel synthetic route to the chemoselectively protected N,S-ditritylglutathione monomethyl ester is described involving the chemical modification of the commercially available glutathione (GSH). The synthetic value of this building block in the facile preparation of GSH bioconjugates in a satisfying overall yield was exemplified by the case of trypanothione disulfide (TS2), a GSH-spermidine bioconjugate, involved in the antioxidative stress protection system of parasitic protozoa, such as trypanosoma and leishmania parasites.
authors.affiliation: Synthetic Organic Chemistry Laboratory, Department of Chemistry, University of Patras , GR-26504 Patras, Greece.
authors.forename: Antonia I
authors.initials: AI
authors.lastname: Antoniou
authors.affiliation: Synthetic Organic Chemistry Laboratory, Department of Chemistry, University of Patras , GR-26504 Patras, Greece.
authors.forename: Dionissia A
authors.initials: DA
authors.lastname: Pepe
authors.forename: Donatella
authors.initials: D
authors.lastname: Aiello
authors.forename: Carlo
authors.initials: C
authors.lastname: Siciliano
authors.affiliation: Synthetic Organic Chemistry Laboratory, Department of Chemistry, University of Patras , GR-26504 Patras, Greece.
authors.forename: Constantinos M
authors.initials: CM
authors.lastname: Athanassopoulos
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis / Q000494:pharmacology; D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D005978:Glutathione / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D007891:Leishmania / Q000187:drug effects; D018384:Oxidative Stress / Q000187:drug effects; D013095:Spermidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D014345:Trypanosoma / Q000187:drug effects
chemical_list: D000975:Antioxidants; D000981:Antiprotozoal Agents; C044809:trypanothione; D005978:Glutathione; D013095:Spermidine