Selection of a specifically blocked mutant of Streptomyces cinnamonensis: isolation and synthesis of 26-deoxymonensin A.
Streptomyces cinnamonensis produces the polyether ionophore antibiotic monensin A. Following a single round of mutagenesis by UV light, a derivative of this strain has been isolated, which secretes a new metabolite identified as 26-deoxymonensin A (3). The structural elucidation of the new metabolite followed from a spectroscopic analysis, and its identity was proven conclusively following a comparison to 26-deoxymonensin A (3) obtained synthetically from monensin A. The preparation of labelled forms of 3 is described, together with incorporation experiments using the parent strain of S. cinnamonensis. Only very low levels of incorporation of 3 into monensin A were observed.
Ashworth
D M
DM
Chemistry Department, The University, Southampton, UK.
Holmes
D S
DS
Robinson
J A
JA
Oikawa
H
H
Cane
D E
DE
D000900:Anti-Bacterial Agents / Q000032:analysis / Q000096:biosynthesis / Q000302:isolation & purification*; D055598:Chemical Phenomena; D002621:Chemistry; D002850:Chromatography, Gel; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D008985:Monensin / Q000031:analogs & derivatives / Q000032:analysis / Q000096:biosynthesis / Q000302:isolation & purification; D009154:Mutation; D013302:Streptomyces / Q000235:genetics / Q000378:metabolism* / Q000528:radiation effects; D014466:Ultraviolet Rays
D000900:Anti-Bacterial Agents; C060472:26-deoxymonensin A; D008985:Monensin