Synthesis of 2-multiprenylphenols and 2-multiprenyl-6-methoxyphenols, biosynthetic precursors of the ubiquinones

Daves, G. Doyle; Moore, Harold W.; Schwab, Donald E.; Olsen, Richard K.; Wilczynski, Joseph J.; Folkers, Karl

doi:10.1021/jo01280a027

Cited by 26 publications

(10 citation statements)

References 1 publication

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“…In the cases of 2-nonaprenylphenol, 2-octaprenylphenol and 6-methoxy-2-nonaprenylphenol sufficient amounts were isolated to obtain u.v. spectra; these were identical with those of authentic samples (Imamoto & Senoh, 1967;Daves et al 1967). The identities of 2-nonaprenylphenol and 6-methoxy-2-nonaprenylphenol were confirmed by mass spectrometry, the samples having parent ions at m/e 706 and 736 respectively.…”

Section: Resultssupporting

confidence: 68%

Biosynthesis of ubiquinone in non-photosynthetic Gram-negative bacteria

Whistance

Brown

Threlfall

1970

Biochemical Journal

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1. The polyprenylphenol and quinone complements of the non-photosynthetic Gram-negative bacteria, Pseudomonas ovalis Chester, Proteus mirabilis and ;Vibrio O1' (Moraxella sp.), were investigated. 2. Ps. ovalis Chester and Prot. mirabilis were shown to contain 2-polyprenylphenols, 6-methoxy-2-polyprenylphenols, 6-methoxy-2-polyprenyl-1,4-benzoquinones, 5-demethoxyubiquinones, ubiquinones, an unidentified 1,4-benzoquinone [2-polyprenyl-1,4-benzoquinone (?)] and ;epoxyubiquinones'. ;Vibrio O1' was shown to contain only 5-demethoxyubiquinones, ubiquinones and ;epoxyubiquinones'. 3. It was established that in Ps. ovalis Chester 2-polyprenylphenols, 6-methoxy-2-polyprenylphenols, 6-methoxy-2-polyprenyl-1,4-benzoquinones, 5-demethoxyubiquinones and 2-polyprenyl-1,4-benzoquinones (?) are precursors of ubiquinones. 4. Intracellular distribution studies showed that in Ps. ovalis Chester ubiquinone and its prenylated precursors are localized entirely on the protoplast membrane. 5. Investigations into the oxygen requirements for ubiquinone biosynthesis by Ps. ovalis Chester showed that the organism could not convert p-hydroxybenzoic acid into ubiquinone in the absence of oxygen, although it could convert a limited amount into 2-polyprenylphenols. 6. Attempts were made to prepare cell-free preparations capable of synthesizing ubiquinone. Purified protoplast membranes of Ps. ovalis Chester were found to be incapable of carrying out this synthesis, even when supplemented with cytoplasm. With crushed-cell preparations of Ps. ovalis Chester, organism PC4 (Achromobacter sp.) and Escherichia coli, synthesis was observed, although this was attributable in part to a small number of intact cells present in the preparations.

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Section: Resultssupporting

confidence: 68%

Biosynthesis of ubiquinone in non-photosynthetic Gram-negative bacteria

Whistance

Brown

Threlfall

1970

Biochemical Journal

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“…This is in accordance with theoretical work on the electronic structure of diphenoquinone. 3 In the same way it has been confirmed that in benzoquinone the absorption in the visible is predominantly polarized along the long molecular axis.4 For 2,3-benzanthracene a short axis polarization of the long-wavelength transition follows in accordance with the theoretical work of Pariser. 6 From these examples it follows that absorption experiments of oriented molecules in an ordered liquid crystal matrix give valuable information about the polarization of optical transitions.…”

supporting

confidence: 54%

Benzocarborane

Hota¹,

Matteson²

1968

J. Am. Chem. Soc.

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“…A pathway for the biosynthesis of ubiquinone has been proposed by Friis, Daves & Folkers (1966). Three of the proposed seven intermediates between 4-hydroxybenzoate and ubiquinone have been isolated from apparently 'wild-type' bacterial cells and identified by spectroscopy and chemical synthesis (Daves et al 1967;Imamoto & Senoh, 1967;Olsen et al 1965Olsen et al , 1966a. However, a methyl multiprenyl-benzoquinone (in this paper 'prenyl' refers to the Cs isoprene unit) has also been detected, and this compound does not fit into the proposed scheme (Friis, Nilsson, Daves & Folkers, 1967).…”

Section: -Hydroxy[u-14c]benzoate Could Be Detected In Cell Extractsmentioning

confidence: 89%

Ubiquinone biosynthesis in Escherichia coli K-12. Accumulation of an octaprenol, farnesylfarnesylgeraniol, by a multiple aromatic auxotroph

Hamilton

Cox

1971

Biochemical Journal

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Cell extracts of a multiple aromatic auxotroph of Escherichia coli K-12, strain AB2830, grown in the absence of precursors of the quinone rings of the ubiquinone and menaquinone molecules, converted 4-hydroxy[U-(14)C]benzoate into a mixture of 3-octaprenyl-4-hydroxybenzoate and 2-octaprenylphenol. An octaprenol, farnesylfarnesylgeraniol, was isolated from such cell extracts and characterized by n.m.r. and mass spectroscopy. Neither the octaprenol, nor polyprenylation of 4-hydroxy[U-(14)C]benzoate, could be detected in cell extracts of strain AB2830 grown in the presence of 0.1mm-4-hydroxybenzoate. It was concluded that, in the biosynthesis of ubiquinone, the polyprenyl side chain is added to 4-hydroxybenzoate as a C(40) unit, the active form of which is converted by cell extracts into farnesylfarnesylgeraniol. The multiple aromatic auxotroph, when grown in the absence of 4-hydroxybenzoate but in the presence of 4-aminobenzoate, converted the latter compound into 3-octaprenyl-4-aminobenzoate. This compound was isolated from whole cells and characterized by n.m.r. and mass spectroscopy.

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Synthesis of 2-multiprenylphenols and 2-multiprenyl-6-methoxyphenols, biosynthetic precursors of the ubiquinones

Cited by 26 publications

References 1 publication

Biosynthesis of ubiquinone in non-photosynthetic Gram-negative bacteria

Biosynthesis of ubiquinone in non-photosynthetic Gram-negative bacteria

Benzocarborane

Ubiquinone biosynthesis in Escherichia coli K-12. Accumulation of an octaprenol, farnesylfarnesylgeraniol, by a multiple aromatic auxotroph

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