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Contribution à l'étude de la structure et de la biosynthèse de glycolipides spécifiques isolés de mycobactéries: les mycosides A et B

Studies on the structure and the biosynthesis of specific glycolipids isolated from mycobacteria: Mycosides A and B

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Abstract

Mycosides are glycosides of p-phenols with a branched glycolic chain the hydroxyl functions of which are esterified with normal and branched chain fatty acids. They differ by the nature and number of sugar molecules which are attached to the phenolic hydroxyl group of the aglycones (Fig. 15).

The structures of the aglycones of mycoside A (isolated fromM. kansasii) and of mycoside B (isolated from bovine strains) are established by oxidative degradation and confirmed by mass spectrometry.

The phenol-glycols A and B differ by the length of the aliphatic glycolic chains. Each aglycone is a mixture of homologues (the fatty acids are homologues and the phenol-glycols are homologues).

The scheme of incorporation of propionic acid into phenol-glycols A and B is the same as the one which has been established for phthiocerol.

Résumé

Les mycosides sont des glycosides de p-phénols ayant une longue chaîne glycolique ramifiée dont les fonctions hydroxyles sont estérifiées par des acides gras normaux et ramifiés. Ils diffèrent par la nature et le nombre des molécules de sucres qui sont fixées sur l'hydroxyle phénolique des aglycones (Fig. 15).

Les structures des aglycones du mycoside A (isolé deM. kansasii) et du mycoside B (isolé de souches bovines) ont été établies par dégradation oxydative et confirmées par spectrométrie de masse.

Les phénol-glycols A et B diffèrent par la longeur des chaînes glycoliques aliphatiques. Chacun des aglycones A et B est un mélange de substances homologues (les acides gras sont des homologues et les phénol-glycols sont des homologues).

L'acide propionique radioactif est incorporé dans les phénol-glycols A et B selon un schéma analogue à celui du phtiocérol. La phénylalanine n'est pas incorporée dans le noyau aromatique des mycosides.

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Author notes

  1. M. Gastambide-Odier

    Present address: Laboratoire de Biochemie Microbienne Faculté des Sciences, B. P. 347, 51 Reims, France

Authors and Affiliations

  1. Institut de Chimie des Substances Naturelles, C.N.R.S., 91-Gif-sur-Yvette, Essonne

    M. Gastambide-Odier & P. Sarda

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  1. M. Gastambide-Odier
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  2. P. Sarda
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Additional information

Ce travail a bénéficié d'une subvention du National Institute of Allergy and Infectious Diseases (U.S. Public Health Service), Grant AI-02838, et d'une subvention du Commissariat à l'Energie Atomique, Saclay, pour l'achat de radioisotopes.

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Gastambide-Odier, M., Sarda, P. Contribution à l'étude de la structure et de la biosynthèse de glycolipides spécifiques isolés de mycobactéries: les mycosides A et B. Pneumologie 142, 241–255 (1970). https://doi.org/10.1007/BF02095222

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