Structure of Phthiocerol | Nature

ABSTRACT PHTHIOCEROL, a characteristic constituent of the waxes of human and bovine strains of tubercle bacilli1–3, was found by Stodola and Anderson1 in 1936 to be a methoxy-glycol with the

formula C34H67(OH)2OCH3 or C35H69(OH)2OCH3. About ten years ago it was shown that phthiocerol has a long-chain structure with a methyl branch in position 4 4–6. More recently the presence

of a β-glycol grouping was demonstrated7,8, and several structural formulæ have been suggested on the basis of degradation experiments (for a review see ref. 9). Definite evidence that the

methoxyl group is attached to carbon atom 3 adjacent to the methyl group was first obtained by a mass spectrometric study of phthiocerol10,11, and this was afterwards confirmed by chemical

studies12–14. The mass-spectrometric results also indicated the presence of a hydroxyl group in position 22 from the straight-chain end of the molecule. The mass spectrum of a purified

sample of phthiocerane, the hydrocarbon obtained by reduction of phthiocerol15, showed this compound to consist mainly of 4-methyltetratriacontane11. Structure (I) for phthiocerol was

suggested on the basis of the mass spectrometric study11. Access through your institution Buy or subscribe This is a preview of subscription content, access via your institution ACCESS

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DERIVATIVES FROM _ASPERGILLUS CALIFORNICUS_ Article 01 October 2020 REFERENCES * Stodola, F. H., and Anderson, R. J., _J. Biol. Chem._, 114, 467 (1936). CAS  Google Scholar  * Reeves, R. E.,

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published). Download references AUTHOR INFORMATION AUTHORS AND AFFILIATIONS * Institut de Biologie physico-chimique, Paris H. DEMARTEAU-GINSBURG & E. LEDERER * Laboratory for Mass

Spectrometry, Karolinska Institutet, Stockholm R. RYHAGE * Institute of Medical Biochemistry, University of Gothenburg, S. STÄLLBERG-STENHAGEN * Institute of Medical Chemistry, University of

Uppsala, E. STENHAGEN Authors * H. DEMARTEAU-GINSBURG View author publications You can also search for this author inPubMed Google Scholar * E. LEDERER View author publications You can also

search for this author inPubMed Google Scholar * R. RYHAGE View author publications You can also search for this author inPubMed Google Scholar * S. STÄLLBERG-STENHAGEN View author

publications You can also search for this author inPubMed Google Scholar * E. STENHAGEN View author publications You can also search for this author inPubMed Google Scholar RIGHTS AND

PERMISSIONS Reprints and permissions ABOUT THIS ARTICLE CITE THIS ARTICLE DEMARTEAU-GINSBURG, H., LEDERER, E., RYHAGE, R. _et al._ Structure of Phthiocerol. _Nature_ 183, 1117–1119 (1959).

https://doi.org/10.1038/1831117a0 Download citation * Issue Date: 18 April 1959 * DOI: https://doi.org/10.1038/1831117a0 SHARE THIS ARTICLE Anyone you share the following link with will be

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