Syntheses of Trehalose Monomycolate and Related Compounds, and Their Lethal Toxicity and Adjuvant Activity

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Abstract
Five monoesters, 6-O-mycoloyl-α, α-treha lose (TMM), 6-O-mycoloyl-D-glucose (GlcM), 6-O-mycoloyl-N-acetyl-D-glucosamine (GlcNAcM), 5-O-mycoloyl-D-arabinose (AraM) and 6-O-mycoloyl-D-galactose (GalM), were synthesized by use of mycolic acid isolated from Mycobacterium tuberculosis strain Aoyama B. Their toxicity and macrophage activating ability were examined in mice. A single intravenous administration of 400 μg of TMM in 9% oil-in-water emulsion killed 8 of 8 treated mice. The other analogs showed less lethal toxicity to mice at the same dose. Tumoricidal activity of mouse peritoneal macrophages was induced by intraperitoneal injection of TMM, GlcM, and GlcNAcM, respectively.