Acylglucoses of the Corynebacteria and Mycobacteria

Abstract

Acylglucoses have been identified as major components of the soluble lipids of Corynebacterium diphtheriae, Mycobacterium smeginatis and BCG, grown in the presence of glucose. These have been purified and the structures determined. All contain one fatty acid per mole of glucose. Mass spectrometry of the methylated lipids and other methylation studies and periodate oxidation indicate that the fatty acids are estcrified to position 6 of the glucose. The major fatty acid of the acylglucose from C. diphtheriae andM. smegrnatis is corynomycolic acid (C,,H,,-CH-CH-COOH).

Identification of 2‐Methyl‐3‐hydroxydecanoic and 2‐Methyl‐3‐hydroxytetradecanoic Acids in the ‘Lipid X’ Fraction of the Bordetella pertussis Endotoxin

“…The formation of higher homologues containing 3 or 4 molecules of 3-hydroxytetradecanoic acids was also observed. [15]. Occurrence of simple a-branched P-hydroxy acid in material of biological origin does not seem to have been reported.…”

The Polar Lipids of Some Species of Nocardia

“…coeliaca by preparative t.1.c. as described previously (Brennan, Lehane & Thomas, 1970). Each showed only glucose and fatty acids on alkaline hydrolysis and their chromatographic properties and fatty acyl to glucose ratios indicated a triacylglucose in N .…”

Microbiotechnology Based Surfactants and Their Applications

“…The other type, trehalose lipids containing corynemycolic acid also carry β-hydroxy-α-branched fatty acid moieties and have been described to occur within the genus Rhodococcus (2, Table 1), carrying 30-56 carbon atoms and within the genus Corynebacterium, carrying 22-36 carbon atoms. They are also described to occur in mycobacteria (Brennan et al, 1970) and found in trehalose lipids of Brevibacterium vitarumen (Lanéelle and Asselineau, 1977), Arthrobacter paraffineus and a Nocardia sp. (Suzuki et al, 1969).…”

“…Complete structures of acylglucoses carrying mycolic acid esters have been elucidated and reported to be produced by isolates belonging to the genera Corynebacterium and Mycobacterium (Brennan et al, 1970) (Table 1), whereas acylglucoses carrying fatty acid esters have been described for Brevibacterium spp. (Okazaki et al, 1969) (Table 2).…”