Stereospecific microbiological 10-O-demethylation of R-(-)-10,11-dimethoxyaporphines.
The microbiological O-dealkylation of (+) and (-) 10,11-dimethoxyaporphine and the corresponding N-n-propyl analog 10,11-dimethoxy-N-n-propylnoraporphine utilizing the fungus Cunninghamella elegans (ATCC 9245) was found to proceed with regioselectivity for the 10-position, and with a high degree of substrate stereospecificity for the 6a R(-)enantiomer. Only the (R) 10-demethylated products were isolated i.e. (R) iosapocodeine and (R) N-n-propylnor-isoapocodeine. The products were confirmed by comparison with their GC/MS spectra.
D001058:Apomorphine / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000378:metabolism; D001711:Biotransformation; D055598:Chemical Phenomena; D002621:Chemistry; D003640:Dealkylation; D008401:Gas Chromatography-Mass Spectrometry; D009090:Mucorales / Q000378:metabolism*; D013237:Stereoisomerism
C044752:isoapocodeine; C044756:10,11-dimethoxy-N-n-propylnoraporphine; C044753:N-n-propylnorisoapocodeine; D001058:Apomorphine