Controlled biosynthesis of neoviridogriseins, new homologues of viridogrisein. III. Production, structures and biological properties of neoviridogriseins I and III.
The high response of our isolate of Streptomyces griseoviridus was exploited to provoke the synthesis of new viridogrisein homologues by adding various amino acids to the culture medium in an attempt to replace the alanine, sarcosine, leucine and phenylsarcosine moieties of virdogrisein. Among the amino acids added, L- and DL-alpha-amino-n-butyric acid and L-methionine gave new TLC spots which we named neoviridogriseins I and III and neoviridogrisein VII, respectively. The structures of neoviridogriseins I and III were elucidated: In both compounds, the alanine moiety of viridogrisein is replaced by a L-alpha-amino-n-butyric acid residue; furthermore, in neoviridogrisein I, the allo-hydroxy-D-proline is replaced by D-proline.
D000596:Amino Acids / Q000032:analysis / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000096:biosynthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D010456:Peptides, Cyclic / Q000096:biosynthesis / Q000494:pharmacology; D013302:Streptomyces / Q000378:metabolism; D013997:Time Factors
D000596:Amino Acids; D000900:Anti-Bacterial Agents; D010456:Peptides, Cyclic