Microbiological oxidation of long-chain aliphatic compounds. Part 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.