Total synthesis and structural revision of the presumed aeruginosins 205A and B

Stephen Hanessian; Xiaotian Wang; Karolina Ersmark; Juan R Del Valle; Ellen Klegraf

doi:10.1021/ol901702k

Total synthesis and structural revision of the presumed aeruginosins 205A and B

Org Lett. 2009 Sep 17;11(18):4232-5. doi: 10.1021/ol901702k.

Authors

Stephen Hanessian¹, Xiaotian Wang, Karolina Ersmark, Juan R Del Valle, Ellen Klegraf

Affiliation

¹ Department of Chemistry, Universite de Montreal, C. P. 6128, Succ. Centre-Ville, Montreal, P. Q., Canada H3C 3J7. stephen.hanessian@umontreal.ca

PMID: 19691354
DOI: 10.1021/ol901702k

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Indoles / chemical synthesis*
Indoles / chemistry
Leucine / analogs & derivatives
Leucine / chemical synthesis
Leucine / chemistry
Molecular Structure*
Stereoisomerism

Substances

Indoles
aeruginosin 298-B
Leucine