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Structural Diversity of 1‐ O ‐Acyl α‐ L ‐Rhamnopyranosides by Precursor‐Directed Biosynthesis with Streptomyces griseoviridis
Author(s) -
Grond Stephanie,
Papastavrou Ina,
Zeeck Axel
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200005)2000:10<1875::aid-ejoc1875>3.0.co;2-g
Subject(s) - chemistry , biosynthesis , stereochemistry , cinnamic acid , substrate (aquarium) , streptomyces , enzyme , organic chemistry , bacteria , oceanography , biology , genetics , geology
The ability of Streptomyces griseoviridis (strain Tü 3634) to glycosylate various carboxylic acids with L ‐rhamnose was investigated by feeding mainly heteroaromatic and aromatic carboxylic acids to growing cultures. The special application of the precursor‐directed biosynthesis (PDB) gave rise to a wide variety of acyl α‐ L ‐rhamnopyranosides as novel metabolites. The experiments resulted in furanyl, pyrrolyl, thienyl, indolyl, and pyridyl derivatives ( 1−8 ), the analogues 9−24 were generated by feeding fluoro‐, hydroxy‐ or aminobenzoic acids or cinnamic acids. All results are discussed with respect to the substrate specificity of the corresponding enzyme system.