Microbial conversion of daunorubicin into N-acetyl-13(S)-dihydrodaunomycin and bisanhydro-13-dihydrodaunomycinone.
By using a strain of Streptomyces willmorii, daunorubicin (daunomycin) was stereoselectively converted into N-acetyl-13(S)-dihydrodaunomycin and bisanhydro-13-dihydrodaunomycinone. The absolute stereochemistry of the new chiral center in N-acetyl-13(S)-dihydrodaunomycin was established by means of nuclear Overhauser effect measured in the 9,13-O-isopropylidene derivative.
D003630:Daunorubicin / Q000031:analogs & derivatives* / Q000378:metabolism*; D005285:Fermentation; D008968:Molecular Conformation; D009279:Naphthacenes / Q000378:metabolism*; D013302:Streptomyces / Q000378:metabolism*
D009279:Naphthacenes; C046898:bisanhydro-13-dihydrodaunomycinone; C046897:N-acetyl-13-dihydrodaunomycin; D003630:Daunorubicin