Archazolid‐7‐O‐β‐D‐glucopyranoside – Isolation, Structural Elucidation and Solution Conformation of a Novel V‐ATPase Inhibitor from the Myxobacterium Cystobacter violaceus

Abstract

AbstractThe novel polyketide macrolide archazolid‐7‐O‐β‐D‐glucopyranoside (3) has been isolated from the myxobacterium Cystobacter violaceus and the structure of this first archazolid‐glycoside has been determined by spectroscopic and degradative methods. A synthesis of simplified 7‐O analogues, based on regioselective derivatisation of archazolid A, was elaborated. These structurally novel archazolids of natural and synthetic origin were evaluated in detail for V‐ATPase inhibition and their biological activities are discussed in terms of their solution conformations, as determined by high‐field NMR studies, including J‐based conformation analysis and constrained molecular dynamics simulations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)