Microbiological oxidation of long-chain aliphatic compounds. IV. Alkane derivatives having polar terminal groups.

Abstract

In a medium containing glucose, Torulopsis gropengiesseri effects ω- and ω-1-hydroxylation of long-chain alkane derivatives having the following groups as terminal substituents: –NO2, –O·SO2·CH3, –NH·SO2·CH3, –NH·CO·CH3, –NH·CO·C3H7, –NH·CO·C4H9, –NH·CO2·C2H5, –CO·NH·CH3, –CO·N(CH3)2, –CN, and –CO·CH3. It is proposed that these hydroxylations are catalysed by an enzyme which is normally responsible for ω-and ω-1-hydroxylation of fatty acids. The yeast also converts 7-(hexylaminocarbonyloxy)heptane into 7-(hexylaminocarbonyloxy)heptanoic acid, and into a glycolipid incorporating 7-(6-hydroxyhexylaminocarbonyloxy)heptanoic acid.