Biosynthesis of the macrolide antibiotic chlorothricin: basic building blocks

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Abstract
The biosynthesis of chlorothricin (I), a macrolide antibiotic isolated from Streptomyces antibioticus [strain] Tu 99 was studied by feeding experiments with 14C- and 3H-labeled precursors. Acetate and propionate, but not methionine and mevalonate, were incorporated into the macrocyclic aglycone of the antibiotic. Glucose and the various C atoms of tyrosine, except the carboxyl C, also contributed label to the aglycone. Glucose also seems to be a specific precursor of the 2-deoxyrhamnose moiety, probably via a process involving a H shift from C-4 to C-6 of the hexose. The substituted 6-methylsalicylic acid moiety seems to be derived from acetate and 1 O-methyl group provided by methionine; shikimic acid is not incorporated.