title: Total synthesis and structural revision of the presumed aeruginosins 205A and B.
abstract: A stereoselective synthesis of enantiopure aeruginosin 205B aglycon confirms the presence of a (3R,2S)-3-chloroleucine amide residue and a (6R)-hydroxy (3aS,7aS)-octahydroindole-(2S)-2-carboxamide [corrected] (Choi) subunit instead of a 6-chloro-substituted core (Ccoi). Enzyme inhibitory tests against thrombin revealed an IC(50) of 0.31 microM. The total synthesis of the presumed aeruginosin 205B shows that the alpha-d-xylopyranosyl unit carries a sulfate group at C-4' (and not at C-3'). Comparison of NMR data leads to the same revision of aeruginosin 205A.
authors.affiliation: Department of Chemistry, Universite de Montreal, C. P. 6128, Succ. Centre-Ville, Montreal, P. Q., Canada H3C 3J7. stephen.hanessian@umontreal.ca
authors.forename: Stephen
authors.initials: S
authors.lastname: Hanessian
authors.forename: Xiaotian
authors.initials: X
authors.lastname: Wang
authors.forename: Karolina
authors.initials: K
authors.lastname: Ersmark
authors.forename: Juan R
authors.initials: JR
authors.lastname: Del Valle
authors.forename: Ellen
authors.initials: E
authors.lastname: Klegraf
mesh_terms: D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007930:Leucine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007211:Indoles; C436761:aeruginosin 298-B; D007930:Leucine