Studies of precursor-directed biosynthesis with streptomyces, 3 - Structural diversity of 1-O-acyl alpha-L-rhamnopyranosides by precursor-directed biosynthesis with Streptomyces griseoviridis

The ability of Streptomyces griseoviridis (strain Tu 3634) to glycosylate v arious carboxylic acids with I-rhamnose was investigated by feeding mainly heteroaromatic and aromatic carboxylic acids to growing cultures. The speci al application of the precursor-directed biosynthesis (PDB) gave rise to a wide variety of acyl alpha-L-rhamnopyranosides as novel metabolites. The ex periments resulted in furanyl, pyrrolyl, thienyl, indolyl, and pyridyl deri vatives (1-8), the analogues 9-24 were generated by feeding fluoro-, hydrox y- or aminobenzoic acids or cinnamic acids. All results are discussed with respect to the substrate specificity of the corresponding enzyme system.