Sur l'isolement et la constitution chimique des acides mycoliques de mycobacterium phlei et de Mycobaterium smegmatis

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.