Biosythesis of corrins. I. Experiments with carbon-14-labeled porphobilinogen and carbon-14-labeled uroporphyrinogens

Ai, Scott; Ca, Townsend; Okada, Kazunori; Kajiwara, M.

doi:10.1021/ja00833a036

Cited by 29 publications

(9 citation statements)

References 27 publications

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“…Further studies with cell-free extracts of Propionibacterium shermanii or Clostridium tetanomorphum (8,25,61,62) showed that cobyrinic acid is biosynthesized from uroporphyrinogen III (urogen III [compound 1]). Urogen III is a key intermediate because of its position at the branch point of two divergent pathways.…”

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confidence: 99%

Purification and characterization of S-adenosyl-L-methionine: uroporphyrinogen III methyltransferase from Pseudomonas denitrificans

et al. 1989

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S-Adenosyl-L-methionine:uroporphyrinogen III methyltransferase (SUMT), the enzyme of the cobalamin biosynthetic pathway which catalyzes C methylation of uroporphyrinogen III, was purified about 150-fold to homogeneity from extracts of a recombinant strain of Pseudomonas denitrificans derived from a cobalamin-overproducing strain by ammonium sulfate fractionation, anion-exchange chromatography, and hydroxyapatite chromatography. The purified protein has an isoelectric point of 6.4 and molecular weights of 56,500 as estimated by gel filtration and 30,000 as estimated by gel electrophoresis under denaturing conditions, suggesting that the active enzyme is a homodimer. It does not contain a chromophoric prosthetic group and does not seem to require metal ions or cofactors for activity. SUMT catalyzes the two successive C-2 and C-7 methylation reactions involved in the conversion of uroporphyrinogen III to precorrin-2 via the intermediate formation of precorrin-1. In vitro studies suggest that the intermediate monomethylated product (precorrin-1) is released from the protein and then added back to the enzyme for the second C-methylation reaction. The pH optimum was 7.7, the Km values for S-adenosyl-L-methionine and uroporphyrinogen III were 6.3 and 1.0 microM, respectively, and the turnover number was 38 h-1. The enzyme activity was shown to be completely insensitive to feedback inhibition by cobalamin and corrinoid intermediates tested at physiological concentration. At uroporphyrinogen III concentrations above 2 microM, SUMT exhibited a substrate inhibition phenomenon. It is suggested that this property might play a regulatory role in cobalamin biosynthesis in the cobalamin-overproducing strain studied.

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confidence: 99%

Purification and characterization of S-adenosyl-L-methionine: uroporphyrinogen III methyltransferase from Pseudomonas denitrificans

et al. 1989

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“…After 144 h, 1 and 2 were efficiently isolated from the culture filtrate as pure compounds, and analyzed by 13 C NMR spectroscopy. Specific incorporations were calculated according to Scott et al [18] NMR signals were analyzed as first-order derivatives or by spin simulation. The results of the 13 C NMR spectral analysis of 2 produced in the tracer experiments are presented in Table 2.…”

Section: Biosynthetic Studiesmentioning

confidence: 99%

Mixed Acetate‐Glycerol Biosynthesis and Formation of Benzoate Directly from Shikimate in Streptomyces sp.

Hoffmann

Grond

2004

Eur J Org Chem

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Keywords: Biosynthesis / Natural products / Lactones / Benzoate biosynthesis / Shikimate / Streptomyces Biosynthetic studies of γ-butyrolactones and 3-furanylcarbonyl α-L-rhamnopyranosides reveal a new mixed biosynthetic pathway which provides different types of secondary metabolites. The new γ-butyrolactone 1 is produced by Streptomyces sp. (strain GT 61150) together with (propenyl-3-furanyl)carbonyl α-L-rhamnopyranoside (2). Their structures were elucidated by chemical and spectroscopic methods. The biosynthesis of 1 and 2 was established by feeding 13 C-labelled acetate and glycerol to Streptomyces sp. and resulted in a complete labelling pattern of 1 and 2.

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“…13 C-NMR analysis of enriched 1 after feeding of individual 13 C-labelled precursors (% specific incorporations (calculated according to Scott et al [10] ) or 13 C-13 C coupling constants) 48 h after inoculation. After 72 h, echinosporin (1) was isolated from the culture filtrate as described, and analysed by 13 C NMR spectroscopy.…”

Section: Feeding Experimentsmentioning

confidence: 99%

“…After 72 h, echinosporin (1) was isolated from the culture filtrate as described, and analysed by 13 C NMR spectroscopy. Specific incorporations were calculated according to Scott et al, [10] 13 C-13 C coupling constants are given, where possible (Table 3).…”

Section: Feeding Experimentsmentioning

confidence: 99%

Biosynthesis of the Antibiotic Echinosporin by a Novel Branch of the Shikimate Pathway

et al. 2002

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Echinosporin (1), a known antibiotic with a unique tricyclic acetal-lactone structure, is produced by Streptomyces erythraeus (strain Tü 4015), together with the novel 7-deoxyechinosporin (2) as minor compound, which was fully characterized. The biosynthesis of 1 was established by feeding experiments with 13 C-labelled precursors. The results revealed that 1 was formed by the shikimate pathway, with chorismate as a biosynthetic intermediate. The proposed mechanism for

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Biosythesis of corrins. I. Experiments with carbon-14-labeled porphobilinogen and carbon-14-labeled uroporphyrinogens

Cited by 29 publications

References 27 publications

Purification and characterization of S-adenosyl-L-methionine: uroporphyrinogen III methyltransferase from Pseudomonas denitrificans

Purification and characterization of S-adenosyl-L-methionine: uroporphyrinogen III methyltransferase from Pseudomonas denitrificans

Mixed Acetate‐Glycerol Biosynthesis and Formation of Benzoate Directly from Shikimate in Streptomyces sp.

Biosynthesis of the Antibiotic Echinosporin by a Novel Branch of the Shikimate Pathway

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