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The Structure of Bactoprenol, a Lipid Formed by Lactobacilli from Mevalonic Acid

Overview
Journal Biochem J
Specialty Biochemistry
Date 1966 Apr 1
PMID 5965329
Citations 24
Authors
K J THORNE
E KODICEK
Affiliations
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Abstract

1. The name ;bactoprenol' has been given to the most abundant lipid formed by three species of lactobacilli from mevalonic acid. 2. A method for the preparation of pure bactoprenol is described. 3. The thin-layer chromatographic properties of bactoprenol and of its acetylated and hydrogenated derivatives resembled those of dolichol. 4. Analysis by mass spectrometry and by nuclear magnetic resonance showed that the molecule is formed by condensation of 10 unsaturated isoprene units and 1 saturated isoprene unit. 5. Its molecular weight is 768 and it has 10 double bonds/molecule. 6. Infrared spectroscopy and the uptake of acetyl groups indicated that the molecule contains a hydroxyl group. 7. It is concluded that bactoprenol is a C(55) isoprenoid alcohol.

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References
1.
CRESSON E, Folkers K, HOFFMAN C, MACRAE G, SKEGGS H, Wolf D . Discovery of a new acetate-replacing factor. J Bacteriol. 1956; 72(4):519-24. PMC: 357945. DOI: 10.1128/jb.72.4.519-524.1956. View
2.
Katz S . The location and tentative identification of steroids on paper chromatograms by means of a system of color tests. Arch Biochem Biophys. 1960; 91:54-60. DOI: 10.1016/0003-9861(60)90454-9. View
3.
THORNE K, KODICEK E . The metabolism of acetate and mevalonic acid by lactob cilli. III. Studies on the unsaponifiable lipids derived from mevalonic acid. Biochim Biophys Acta. 1962; 59:295-306. DOI: 10.1016/0006-3002(62)90177-4. View
4.
Pennock J, Hemming F, Morton R . Dolichol: a naturally occurring isoprenoid alcohol. Nature. 1960; 186:470-2. View
5.
Burgos J, Hemming F, Pennock J, Morton R . DOLICHOL: A NATURALLY-OCCURRING C100 ISOPRENOID ALCOHOL. Biochem J. 1963; 88:470-82. PMC: 1202202. View