Abstract
Microbial transformation of the amide congeners of lysergic acid diethylamide (LSD) by Streptomyces roseochromogenes was examined. Derivatives having no methylene group at the (ω-1) position of the amine alkyl chain of the amide function, lysergic acid dimethylamide (LDM) and lysergic acid diallylamide (LDA), were oxidized at the α-position of the amide nitrogen to give the corresponding N-dealkylated products, lysergic acid methylamide (LAM) and lysergic acid allylamide (LAA). On the other hand, derivatives having a methylene group at the (ω-1) position, lysergic acid di-n-propylamide (LDP) and lysergic acid di-n-butylamide (LDB), were oxidized at the (ω-1) position to give pairs of (ω-1) hydroxylation products, 2-hydroxy-LDP and epi-2-hydroxyLDP, and 3-hydroxyLDB and epi-3-hydroxyLDB, together with the corresponding ketomethyl products, 2-oxoLDP and 3-oxoLDB. The predominant formation of 2-hydroxyLDP in the case of LDP indicated that (ω-1) hydroxylation occurred stereospecifically.
