Ansamycin biogenesis: Incorporation of [1‐<sup>13</sup>C]glucose and [1‐<sup>13</sup>C]glycerate into the chromophore of rifamycin S

White, Richard; Martinelli, E.

doi:10.1016/0014-5793(74)80519-3

Cited by 43 publications

(19 citation statements)

References 11 publications

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“…This structural element is present in a number of diverse natural products, for example, geldanamycin, pactamycin, rifamycin, and validamycin A. [163-165] …”

Section: Biosynthesismentioning

confidence: 99%

Mitomycinoid Alkaloids: Mechanism of Action, Biosynthesis, Total Syntheses, and Synthetic Approaches

et al. 2013

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“…This structural element is present in a number of diverse natural products, for example, geldanamycin, pactamycin, rifamycin, and validamycin A. [163-165] …”

Section: Biosynthesismentioning

confidence: 99%

Mitomycinoid Alkaloids: Mechanism of Action, Biosynthesis, Total Syntheses, and Synthetic Approaches

et al. 2013

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“…The mC 7 N unit of validamycin and acarbose arises from 2-epi-5-epi-valiolone, a product of the cyclization of seduheptulose 7-phosphate, 14 that of pactamycin from the shikimate pathway via 3-aminobenzoic acid, 15 and those of asukamycin and manumycin from 3-amino-4-hydroxybenzoic acid, which arises from the condensation of a triose phosphate and a C 4 -dicarboxylic acid. 16 The incorporation patterns of labeled precursors into several ansamycins and into mitomycins, 13,[17][18][19] as well as mutant complementation studies 20 all suggested a shikimate pathway origin of the mC 7 N unit, but attempts to incorporate labeled shikimic acid, quinic acid or 3-dehydroquinic acid were unsuccessful. 17,19,[21][22][23] The nonincorporation of shikimic acid could be because of permeability barriers.…”

Section: Historymentioning

confidence: 99%

The biosynthesis of 3-amino-5-hydroxybenzoic acid (AHBA), the precursor of mC7N units in ansamycin and mitomycin antibiotics: a review

2010

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The aminoshikimate pathway of formation of 3-amino-5-hydroxybenzoic acid (AHBA), the precursor of ansamycin and other antibiotics is reviewed. In this biosynthesis, genes for kanosamine formation have been recruited from other genomes, to provide a nitrogenous precursor. Kanosamine is then phosphorylated and converted by common cellular enzymes into 1-deoxy-1-imino-erythrose 4-phosphate, the substrate for the formation of aminoDAHP. This is converted via 5-deoxy-5-aminodehydroquinic acid and 5-deoxy-5-aminodehydroshikimic acid into AHBA. Remarkably, the pyridoxal phosphate enzyme AHBA synthase seems to have two catalytic functions: As a homodimer, it catalyzes the last reaction in the pathway, the aromatization of 5-deoxy-5-aminodehydroshikimic acid, and at the beginning of the pathway in a complex with the oxidoreductase RifL it catalyzes the transamination of UDP-3-keto-D-glucose. The AHBA synthase gene also serves as a useful tool in the genetic screening for new ansamycins and other AHBA-derived natural products.

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“…AHBA is synthesized via a variant of the shikimate pathway of aromatic biosynthesis (Ghisalba and Nüesch, 1978a, b;White and Martinelli, 1974). DAHP synthase is the first enzyme of the shikimate pathway, and its activity is inhibited by the three aromatic amino acids (Fig.…”

Section: Discussionmentioning

confidence: 99%

“…The rifamycins are produced by Amycolatopsis mediterranei (Sensi et al, 1959), and their biosynthesis involves a polyketide intermediate synthesized with chain extension of an unusual starter unit, 3-amino-5-hydroxybenzoic acid (AHBA) (Ghisalba and Nüesch, 1981;Kibby et al, 1980), and its assembly with two acetate and eight propionate units on a type I polyketide synthase (PKS) (Lancini and Carvelieri, 1997). AHBA is in turn synthesized via a variant of the shikimate pathway of aromatic amino acid biosynthesis (Ghisalba and Nüesch, 1978a, b;White and Martinelli, 1974). 3-Deoxy-D-arabino-heptulosonate-7-phosphate (DAHP) synthase is the first enzyme of the shikimate pathway, and its activity is inhibited by three aromatic amino acids.…”

Section: Introductionmentioning

confidence: 99%

Improvement of industry-applied rifamycin B-producing strain, Amycolatopsis mediterranei, by rational screening.

Jin

Lin

et al. 2002

J. Gen. Appl. Microbiol.

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An industrially applied rifamycin B-producing strain, Amycolatopsis mediterranei XC 1-02, was used for further screening. A special mutation and screening procedure was adopted to select a strain, which can alleviate the inhibition caused by both aromatic amino acid and p-hydroxybenzoic acid in the pathway of rifamycin B biosynthesis as well as enhance the production of propionate, one of the precursors of rifamycin B biosynthesis. By the above methods, a strain A. mediterranei XC 9-25 was obtained, and its rifamycin B productivity in shaking flask reaches 10 g/L, which is 2.38 times higher than that of the ancestral strain XC 1-02. The productivity of rifamycin B fed-batch fermentation in 60,000 L fermentor with A. mediterranei XC 9-25 reached 19.11 g/L.

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Ansamycin biogenesis: Incorporation of [1‐¹³C]glucose and [1‐¹³C]glycerate into the chromophore of rifamycin S

Cited by 43 publications

References 11 publications

Mitomycinoid Alkaloids: Mechanism of Action, Biosynthesis, Total Syntheses, and Synthetic Approaches

Mitomycinoid Alkaloids: Mechanism of Action, Biosynthesis, Total Syntheses, and Synthetic Approaches

The biosynthesis of 3-amino-5-hydroxybenzoic acid (AHBA), the precursor of mC7N units in ansamycin and mitomycin antibiotics: a review

Improvement of industry-applied rifamycin B-producing strain, Amycolatopsis mediterranei, by rational screening.

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Ansamycin biogenesis: Incorporation of [1‐13C]glucose and [1‐13C]glycerate into the chromophore of rifamycin S

Cited by 43 publications

References 11 publications

Mitomycinoid Alkaloids: Mechanism of Action, Biosynthesis, Total Syntheses, and Synthetic Approaches

Mitomycinoid Alkaloids: Mechanism of Action, Biosynthesis, Total Syntheses, and Synthetic Approaches

The biosynthesis of 3-amino-5-hydroxybenzoic acid (AHBA), the precursor of mC7N units in ansamycin and mitomycin antibiotics: a review

Improvement of industry-applied rifamycin B-producing strain, Amycolatopsis mediterranei, by rational screening.

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Product

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Ansamycin biogenesis: Incorporation of [1‐¹³C]glucose and [1‐¹³C]glycerate into the chromophore of rifamycin S