Biogenetic Studies on Oxazolomycin, a Metabolite of Streptomyces albus (Strain JA 3453)

Liebigs Annalen der Chemie
1992.0

Abstract

<jats:title>Abstract</jats:title><jats:p>Feeding experiments with sodium [<jats:sup>13</jats:sup>C]‐labelled acetate, sodium [1‐<jats:sup>13</jats:sup>C]propionate, <jats:sc>L</jats:sc>‐[<jats:italic>methyl</jats:italic>‐<jats:sup>13</jats:sup>C]methionine, <jats:sc>L</jats:sc>‐[1‐<jats:sup>13</jats:sup>C]‐alanine, and [1‐<jats:sup>13</jats:sup>C]glycine on <jats:italic>Streptomyces albus</jats:italic> (strain JA 3453) produced oxazolomycin (<jats:bold>1</jats:bold>), whose NMR analysis provided information about the biogenetic construction of its carbon skeleton. Both the (<jats:italic>E</jats:italic>,<jats:italic>E</jats:italic>)‐diene and the (<jats:italic>Z</jats:italic>,<jats:italic>Z</jats:italic>,<jats:italic>E</jats:italic>)‐triene chains are built up from acetate via the polyketide pathway each starting with a glycine‐derived building block. The use of glycine predicts an uncommon biosynthetic pathway leading to oxazole rings in actinomycetes. The spiro‐ring system in <jats:bold>1</jats:bold> is formed from acetate, glycine, and a C<jats:sub>3</jats:sub> unit of unknown origin. The oxazolomycin producing organism combines carbon, oxygen, and nitrogen methylation activity via methionine (C<jats:sub>1</jats:sub> pool) for the biosynthesis of <jats:bold>1</jats:bold>.

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