Abstract
The strain of Mycobacterium phlei that has been studied contains two dextrotatory mycolic acids which are called α- and gb-phlei-mycolic acids. They can only be distingished by chromatography on alumina and infrared spectrography. The two acids contain no methoxyl and correspond to the molecular formula C 83H 166O 4 ± 5CH 2. The strain of M. smegmatis that has been studied contains three smegma-mycolic acids (α: mp. 61°, β: m.p. 61°, and γ: m.p. 70°); these acids are also dextrorotatory, contain no methoxyl and correspond to the molecular formular C 83 H 166O 4 ± 5CH 2. The five mycolic acids described here yield tetrasonic acid on pyrolysis and have the strutural formula ▪ where R is an aliphatic hydroxyl-containing residue C 58H 177O having at least two chains. The strutural formula proposed for α-smegma-mycolic acid is ▪ In contrast to the human and bovine strains of M. tuberculosis, the two saprophyte strains examined here seem incapable of synthesizing hexacosanoic acid; in these strains tetracosanic acid is the highest member of the series of normal fatty acids. We think that this explains why the mycolic acids from saprophyte strains have a side chain C 22H 45 in the α-position of the carboxyl group while the mycolic acids from M. tuberculosis have a corresponding side chain C 24H 49.
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