Total synthesis and structural revision of the presumed aeruginosins 205A and B.
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.
Hanessian
Stephen
S
Department of Chemistry, Universite de Montreal, C. P. 6128, Succ. Centre-Ville, Montreal, P. Q., Canada H3C 3J7. stephen.hanessian@umontreal.ca
Wang
Xiaotian
X
Ersmark
Karolina
K
Del Valle
Juan R
JR
Klegraf
Ellen
E
D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007930:Leucine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D007211:Indoles; C436761:aeruginosin 298-B; D007930:Leucine