Total synthesis of the cyclic heptapeptide Argyrin B: a new potent inhibitor of T-cell independent antibody formation.
[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.
Ley
Steven V
SV
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK. svl1000@cam.ac.uk
Priour
Alain
A
Heusser
Christoph
C
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
D007166:Immunosuppressive Agents; D007211:Indoles; D009842:Oligopeptides; D010456:Peptides, Cyclic; C467071:argyrin B