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Mycobacterial sulfolipids: Spontaneous desulfation
Author(s) -
Goren Mayer B.
Publication year - 1971
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02536373
Subject(s) - chemistry , anhydrous , glycolipid , ammonium sulfate , salt (chemistry) , reagent , biochemistry , trehalose , choline , chromatography , organic chemistry
A glycolipid sulfate elaborated in abundance by surface‐grown cultures of Mycobacterium tuberculosis has been characterized in earlier studies as a complex 2,3,6,6′‐tetraacyl α, α′ trehalose 2′‐sulfate. The purified ammonium salt undergoes rapid quantitative desulfation on mere dissolution in reagent grade anhydrous ether. The same reaction is observed in sulfolipids recovered from a number of human strains and one bovine strain. Experimental observations on the normal and acid‐catalyzed rates of the reaction and on the influence of other solvents and other cationic forms support a proposed mechanism, which is detailed. Structural criteria which may influence the proclivity for spontaneous desulfation are discussed.