The Chemistry of the Lipids of Tubercle Bacilli. XLIV. Comparative Study of the Lipids of the Human Tubercle Bacillus¹

Abstract

w-Heptaldehyde Me-n-Hex Me-«-Am ketones EtOAc Moles used 8.0 9.4 6.2 8.3 ( )-Methylnonanol-( ) 2,3 3,3 4,4 5,5 Intermediate products Yield, % 66 77 76 79 B. p. (10 mm.), °C. 90-95 87-88 86-87 83-86 «20 d 1.435 1.436 1.434 1.434 ^J (

Component acids of the lipids of human tubercle bacilli. Part 1

“…Tuberculostearic acid and phthioic acid, isolated by the above procedure from the acetone-soluble fat of the human type tubercle bacillus, strain H-37, appeared to be characteristic components of the lipids of human tubercle bacilli, although the composition ofthe lipids was found to vary from strain to strain (cf. Crowder, Stodola, Pangborn & Anderson, 1936). More recently studies of cell residues from the preparation of the purified tuberculin protein PPD, derived from an unidentified strain of the human tubercle bacillus, indicated the presence of various branched-chain fatty acids which had not been encountered in previous investigations (Peck & Anderson, 1941;Edens, Creighton & Anderson, 1944;Ginger & Anderson, 1944).…”

Structural Peculiarities of Acid-fast Bacterial Lipids.

“…It must be admitted that none of these studies is complete, but we believe that a general outline is evident and that the results that we have obtained can be reproduced, but certain reservations are necessary. It has been found (27), for instance, that five different strains of the human tubercle bacillus which were cultivated under identical conditions showed great variation in chemical constants and in the proportions of the various compounds. However, they all contained the same characteristic components although in varying amounts.…”

Liquid and Solid Acids as Catalysts for the Thiele–Winter reaction of Menadione

“…We have been interested in the synthesis of phthiocol (2hydroxy-3-methyl-1,4-naphthoquinone) (3), an antibiotic substance produced by Mycobacterium tuberculosis and some plants 4 . Our synthesis of phthiocol involves the transformation of methylnaphthoquinone (menadione) (1) into 1,2,4-triacetoxy-3-methylnaphthalene (2) by a Thiele-Winter reaction, and then the saponification of (2) followed by its catalytic oxidation into phthiocol (3) (Scheme 1).…”