The characterization of undecaprenol of <i>Lactobacillus plantarum</i>

Gough, Doreen P.; Kirby, Alison L.; Richards, J. B.; Hemming, Frank W.

doi:10.1042/bj1180167

Cited by 50 publications

(35 citation statements)

References 14 publications

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“…Unquestionable evidence is for instance given by the normal incorporation of [2-13C]-or [1,2-'3C2-acetate into the isoprenic moiety of antibiotics from several Actinomycetes [29][30][31][32]. Although the radioactivity has usually not been localized, the incorporation of 14C and, in one case of 13C labelled mevalonate into bacterial isoprenoids of different series (C30 and C40 carotenoids, acyclic polyprenol derivatives, isopentenyladenosine, sterols), is also in favour of the occurrence of the classical pathway [33][34][35][36][37][38][39][40][41][42][43][44]. This pathway is also present in the Archaebacteria examined so far, as shown by the incorporation of labelled acetate, mevalonate, glycerol or glucose into the lipids containing phytanyl chains of the thermoacidophilic Caldariella acidophila [4] or the halophilic Halobacterium species [45][46][47][48] and by the conversion of HMG-CoA into MVA by enzymic preparations from the latter bacteria [49].…”

Section: Results and Discussion Incorporation Of 13c-labelled Precursmentioning

confidence: 93%

Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate

Rohmer

Knani

Simonin

et al. 1993

Biochemical Journal

1,079

697

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Incorporation of 13C-labelled glucose, acetate, pyruvate or erythrose allowed the determination of the origin of the carbon atoms of triterpenoids of the hopane series and/or of the ubiquinones from several bacteria (Zymomonas mobilis, Methylobacterium fujisawaense, Escherichia coli and Alicyclobacillus acidoterrestris) confirmed our earlier results obtained by incorporation of 13C-labelled acetate into the hopanoids of other bacteria and led to the identification of a novel biosynthetic route for the early steps of isoprenoid biosynthesis. The C5 framework of isoprenic units results most probably (i) from the condensation of a C2 unit derived from pyruvate decarboxylation (e.g. thiamine-activated acetaldehyde) on the C-2 carbonyl group of a triose phosphate derivative issued probably from dihydroxyacetone phosphate and not from pyruvate and (ii) from a transposition step. Although this hypothetical biosynthetic pathway resembles that of L-valine biosynthesis, this amino acid or its C5 precursors could be excluded as intermediates in the formation of isoprenic units.

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Section: Results and Discussion Incorporation Of 13c-labelled Precursmentioning

confidence: 93%

Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate

Rohmer

Knani

Simonin

et al. 1993

Biochemical Journal

1,079

697

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“…P.G. has been shown to be mevalonate-derived [6] and, more recently, lanosterol and hopanoid biosynthesis has been described for Methylococcus capsulatus [7]. A pentaketide chain supplemented with the two methionine-derived carbons comprises a Ca2 moiety which is linked with a C 9 fatty acid by a C 5 moiety.…”

Section: Introductionmentioning

confidence: 99%

A role for 3-hydroxy-3-methyl-glutaric acid in the biosynthesis of pseudomonic acid A

Mantle

1988

FEMS Microbiology Letters

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[3‐14C]3‐Hydroxy‐3‐methyl‐glutaric acid (HMG) was incorporated (0.9%) into pseudomonic acid A when administered to a shaken flask fermentation of Pseudomonas fluorescens 4, 9 and 14 h after inoculation. [2‐14C]‐Mevalonic acid was not incorporated into pseudomonic acid. Experimental evidence supports the previous deduction that pseudomonic acid biosynthesis might directly involve HMG, an apparently unusual intermediary metabolite in prokaryotes.

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“…11,23 Such an alcohol intermediate is not found in the C 55 -PP pathway in prokaryotes. However, a significant pool of undecaprenol (C 55 -OH) has been observed in many Gram-positive bacteria, 3,35,44,108 whose origin and function are not clearly established. In eukaryotes, dolichol is FIG.…”

Section: Formation and Role Of C 55 -P Derivativesmentioning

confidence: 99%

Deciphering the Metabolism of Undecaprenyl-Phosphate: The Bacterial Cell-Wall Unit Carrier at the Membrane Frontier

Manat

Roure

Auger

et al. 2014

Microbial Drug Resistance

121

139

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During the biogenesis of bacterial cell-wall polysaccharides, such as peptidoglycan, cytoplasmic synthesized precursors should be trafficked across the plasma membrane. This essential process requires a dedicated lipid, undecaprenyl-phosphate that is used as a glycan lipid carrier. The sugar is linked to the lipid carrier at the inner face of the membrane and is translocated toward the periplasm, where the glycan moiety is transferred to the growing polymer. Undecaprenyl-phosphate originates from the dephosphorylation of its precursor undecaprenyl-diphosphate, with itself generated by de novo synthesis or by recycling after the final glycan transfer. Undecaprenyl-diphosphate is de novo synthesized by the cytosolic cis-prenyltransferase undecaprenyldiphosphate synthase, which has been structurally and mechanistically characterized in great detail highlighting the condensation process. In contrast, the next step toward the formation of the lipid carrier, the dephosphorylation step, which has been overlooked for many years, has only started revealing surprising features. In contrast to the previous step, two unrelated families of integral membrane proteins exhibit undecaprenyldiphosphate phosphatase activity: BacA and members of the phosphatidic acid phosphatase type 2 super-family, raising the question of the significance of this multiplicity. Moreover, these enzymes establish an unexpected link between the synthesis of bacterial cell-wall polymers and other biological processes. In the present review, the current knowledge in the field of the bacterial lipid carrier, its mechanism of action, biogenesis, recycling, regulation, and future perspective works are presented.

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The characterization of undecaprenol of Lactobacillus plantarum

Cited by 50 publications

References 14 publications

Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate

Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate

A role for 3-hydroxy-3-methyl-glutaric acid in the biosynthesis of pseudomonic acid A

Deciphering the Metabolism of Undecaprenyl-Phosphate: The Bacterial Cell-Wall Unit Carrier at the Membrane Frontier

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