The Characterization of Undecaprenol of Lactobacillus Plantarum

Overview

Journal Biochem J

Specialty Biochemistry

Date 1970 Jun 1

PMID 5472148

Citations 11

Authors

D P Gough

A L Kirby

J B Richards

F W Hemming

Affiliations

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Abstract

Evidence for the presence of undecaprenol in the unsaponifiable lipid of Lactobacillus plantarum (N.C.I.B. 6376) is presented. Characterization of the compound was based mainly on mass, i.r. and n.m.r. spectrometry. The prenol was isolated at a concentration of 40mug/g wet wt. of bacteria and contained over 90% (1.0-5.4% of the dose) of the (14)C present in the unsaponifiable lipid after incubation of the bacteria with [2-(14)C]mevalonate. N.m.r. spectrometry indicated the presence of two internal trans-, one alpha-cis- and seven internal cis-isoprene residues per molecule. The (3)H/(14)C ratios of the prenol after incubation of the bacteria with [2-(14)C,(4R)-4-(3)H(1)]- and [2-(14)C,(4S)-4-(3)H(1)]-mevalonate were in agreement with this stereochemistry. There was no evidence of saturated isoprene residues in the molecule. The undecaprenol appeared to be accompanied by much smaller quantities of decaprenol and nonaprenol.

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References

Dunphy P, Whittle K, Pennock J . On the use of fluorescein and dichlorofluorescein as non-destructive stains for lipids. Chem Ind. 1965; 27:1217-8. View

THORNE K, KODICEK E . The structure of bactoprenol, a lipid formed by lactobacilli from mevalonic acid. Biochem J. 1966; 99(1):123-7. PMC: 1264965. DOI: 10.1042/bj0990123. View

Wellburn A, Stevenson J, Hemming F, Morton R . The characterization and properties of castaprenol-11, -12 and -13 from the leaves of Aesculus hippocastanum (horse chestnut). Biochem J. 1967; 102(1):313-24. PMC: 1270242. DOI: 10.1042/bj1020313. View

Wright A, Dankert M, Fennessey P, Robbins P . Characterization of a polyisoprenoid compound functional in O-antigen biosynthesis. Proc Natl Acad Sci U S A. 1967; 57(6):1798-803. PMC: 224549. DOI: 10.1073/pnas.57.6.1798. View

Higashi Y, Strominger J, Sweeley C . Structure of a lipid intermediate in cell wall peptidoglycan synthesis: a derivative of a C55 isoprenoid alcohol. Proc Natl Acad Sci U S A. 1967; 57(6):1878-84. PMC: 224560. DOI: 10.1073/pnas.57.6.1878. View

Feeney J, Hemming F . Nuclear magnetic resonance spectrometry of naturally occurring polyprenols. Anal Biochem. 1967; 20(1):1-15. DOI: 10.1016/0003-2697(67)90258-8. View

Stone K, Hemming F . The stereochemistry of hexahydroprenol, ubiquinone and ergosterol biosynthesis in the mycelium of Aspergillus fumigatus Fresenius. Biochem J. 1967; 104(1):43-56. PMC: 1270544. DOI: 10.1042/bj1040043. View

Scher M, Lennarz W, Sweeley C . The biosynthesis of mannosyl-1-phosphoryl-polyisoprenol in Micrococcus lysodeikticus and its role in mannan synthesis. Proc Natl Acad Sci U S A. 1968; 59(4):1313-20. PMC: 224869. DOI: 10.1073/pnas.59.4.1313. View

Gough D, Hemming F . The stereochemistry of betulaprenol biosynthesis. Biochem J. 1970; 117(2):309-17. PMC: 1178863. DOI: 10.1042/bj1170309. View

10.

Gough D, Hemming F . The characterization and stereochemistry of biosynthesis of dolichols in rat liver. Biochem J. 1970; 118(1):163-6. PMC: 1179092. DOI: 10.1042/bj1180163. View

11.

Hemming F . Polyprenols. Biochem Soc Symp. 1970; 29:105-17. View

12.

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

13.

THORNE K, KODICEK E . The metabolism of acetate and mevalonic acid by lactobacilli. I. The effect of acetate and mevalonic acid on growth. Biochim Biophys Acta. 1962; 59:273-9. DOI: 10.1016/0006-3002(62)90175-0. View

14.

Durr I, SHWAYRI A . METABOLISM OF MEVALONIC ACID BY LACTOBACILLUS PLANTARUM. J Bacteriol. 1964; 88:361-6. PMC: 277308. DOI: 10.1128/jb.88.2.361-366.1964. View

15.

THORNE K, KODICEK E . The metabolism of acetate and mevalonic acid by lactobacilli. II. The incorporation of [14C]acetate and [14C]mevalonic acid into the bacterial lipids. Biochim Biophys Acta. 1962; 59:280-94. DOI: 10.1016/0006-3002(62)90176-2. View