MICROBIOLOGICAL OXYGENATION OF ALICYCLIC AMIDES

Continuing our broad study of the microbiological oxygenation of simple monocyclic systems, a series of N-cycloalkylamides and N,N-dicycloalkylamides was subjected to fermentation by Sporotrichum sulfurescens. Consonant with the hypothetical enzyme-substrate model proposed earlier, N-cyclododecylacetamide was monooxygenated at the 5, 6, and 7 positions, while a variety of N-cyclohexylamides and N-cycloheptylamides underwent oxygenation at the 4 position. N-Cyelooctylamides gave two products, thought to be monoxygenated at the 4 and 5 positions. When confronted with two alicyclic rings of different sizes in the same N,N-dicycloalkylacetamide molecule, the organism seemed to prefer the cycloheptyl to the cyclohexyl ring, and showed little tendency to attack a cyclopentyl ring. © 1968, American Chemical Society. All rights reserved.