6‐Deoxy‐α‐L‐talopyranosides from Streptomyces sp.

European Journal of Organic Chemistry
2006.0

Abstract

<jats:title>Abstract</jats:title><jats:p><jats:italic>Streptomyces</jats:italic> sp. strain GöM1 was found to produce seven novel glycosides (<jats:bold>2</jats:bold>–<jats:bold>8</jats:bold>) containing the rare deoxysugar 6‐deoxy‐α‐<jats:sc>L</jats:sc>‐talose. The aglycones are small phenols, isovaleric acid or aromatic carboxylic acids. By precursor‐directed biosynthesis, the yields of the compounds could be increased significantly. Feeding of 4‐hydroxybenzoic acid led to the production of both acyl and aryl glycosides, and of compound <jats:bold>9</jats:bold> with both structural elements. Pyrrol‐2‐ylcarbonyl 6‐deoxy‐α‐<jats:sc>L</jats:sc>‐talopyranoside (<jats:bold>6</jats:bold>) shows remarkable growth inhibition of some parasites. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2006)

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