title: Thiazolidine-Protected β-Thiol Asparagine: Applications in One-Pot Ligation-Desulfurization Chemistry.
abstract: The synthesis of a β-thiol asparagine derivative bearing a novel (2,4,6-trimethoxyphenyl)thiazolidine protecting group is described. The efficient incorporation of the amino acid into the N-termini of peptides is demonstrated as well as the utility of the β-thiol asparagine moiety for rapid ligation reactions with peptide thioesters. The streamlined synthesis of native peptide products could be accomplished using a one-pot radical desulfurization of the β-thiol auxiliary following the ligation event. The utility of the amino acid is highlighted in the efficient one-pot assembly of the HIV entry inhibitor enfuvirtide.
authors.affiliation: School of Chemistry, The University of Sydney , Sydney, New South Wales 2006, Australia.
authors.forename: Jessica
authors.initials: J
authors.lastname: Sayers
authors.affiliation: School of Chemistry, The University of Sydney , Sydney, New South Wales 2006, Australia.
authors.forename: Robert E
authors.initials: RE
authors.lastname: Thompson
authors.affiliation: School of Chemistry, The University of Sydney , Sydney, New South Wales 2006, Australia.
authors.forename: Kristen J
authors.initials: KJ
authors.lastname: Perry
authors.affiliation: School of Chemistry, The University of Sydney , Sydney, New South Wales 2006, Australia.
authors.forename: Lara R
authors.initials: LR
authors.lastname: Malins
authors.affiliation: School of Chemistry, The University of Sydney , Sydney, New South Wales 2006, Australia.
authors.forename: Richard J
authors.initials: RJ
authors.lastname: Payne
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001216:Asparagine / Q000737:chemistry*; D000077560:Enfuvirtide; D015700:HIV Envelope Protein gp41 / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D010446:Peptide Fragments / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D053778:Thiazolidines / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D019380:Anti-HIV Agents; D015700:HIV Envelope Protein gp41; D010446:Peptide Fragments; D013438:Sulfhydryl Compounds; D053778:Thiazolidines; D000077560:Enfuvirtide; D001216:Asparagine