title: Total synthesis of the cyclic heptapeptide Argyrin B: a new potent inhibitor of T-cell independent antibody formation.
abstract: [structure: see text] The total synthesis of Argyrin B (1) is presented using a synthetic plan that is convergent and flexible and conserves the stereogenic centers. The unusual amino acid 4-methoxy tryptophan (6) was obtained via an enzymatic resolution. Cyclization followed by oxidative elimination of the phenylseleno cysteine to the sensitive dehydroalanine afforded synthetic 1.
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK. svl1000@cam.ac.uk
authors.forename: Steven V
authors.initials: SV
authors.lastname: Ley
authors.forename: Alain
authors.initials: A
authors.lastname: Priour
authors.forename: Christoph
authors.initials: C
authors.lastname: Heusser
mesh_terms: D000818:Animals; D000917:Antibody Formation / Q000187:drug effects; D006801:Humans; D007166:Immunosuppressive Agents / Q000138:chemical synthesis; D007211:Indoles / Q000737:chemistry; D009842:Oligopeptides / Q000138:chemical synthesis*; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D014183:Transplantation, Heterologous / Q000276:immunology
chemical_list: D007166:Immunosuppressive Agents; D007211:Indoles; D009842:Oligopeptides; D010456:Peptides, Cyclic; C467071:argyrin B