The biosynthesis of shikimate metabolites

Dewick, P. M.

doi:10.1039/np9890600263

Cited by 15 publications

(3 citation statements)

References 60 publications

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“…Besides acting as precursor for 3-hydroxyanthranilic acid, chorismate is the precursor of phenylalanine, tryptophan, and tyrosine [29]. Amino acid synthesis is feedback-regulated by its own products [30]. When primary and specialized metabolite biosynthesis utilize the same precursor, the feedback regulation can impact the production of specialized metabolites.…”

Section: Discussionmentioning

confidence: 99%

Influence of Amino Acid Feeding on Production of Calcimycin and Analogs in Streptomyces chartreusis

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Bandow

2021

IJERPH

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Streptomyces chartreusis NRRL 3882 produces the polyether ionophore calcimycin and a variety of analogs, which originate from the same biosynthetic gene cluster. The role of calcimycin and its analogs for the producer is unknown, but calcimycin has strong antibacterial activity. Feeding experiments were performed in chemically defined medium systematically supplemented with proteinogenic amino acids to analyze their individual effects on calcimycin synthesis. In the culture supernatants, in addition to known calcimycin analogs, eight so far unknown analogs were detected using LC-MS/MS. Under most conditions cezomycin was the compound produced in highest amounts. The highest production of calcimycin was detected upon feeding with glutamine. Supplementation of the medium with glutamic acid resulted in a decrease in calcimycin production, and supplementation of other amino acids such as tryptophan, lysine, and valine resulted in the decrease in the synthesis of calcimycin and of the known intermediates of the biosynthetic pathway. We demonstrated that the production of calcimycin and its analogs is strongly dependent on amino acid supply. Utilization of amino acids as precursors and as nitrogen sources seem to critically influence calcimycin synthesis. Even amino acids not serving as direct precursors resulted in a different product profile regarding the stoichiometry of calcimycin analogs. Only slight changes in cultivation conditions can lead to major changes in the metabolic output, which highlights the hidden potential of biosynthetic gene clusters. We emphasize the need to further study the extent of this potential to understand the ecological role of metabolite diversity originating from single biosynthetic gene clusters.

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Section: Discussionmentioning

confidence: 99%

Influence of Amino Acid Feeding on Production of Calcimycin and Analogs in Streptomyces chartreusis

Arend

Bandow

2021

IJERPH

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“…The biosynthesis of flavone C-glucosides has been shown to occur via glucosylation of 2-hydroxyflavanones, and not via flavones (see ref. 1). A UDPglucose : 2-hydroxyflavanone-6 (or 8)-C-glucosyltransferase from cotyledons of buckwheat (Fagopyrum esculenturn) has been purified and its substrate specificity investigated.…”

Section: Flavanones Dihydroflavonols Anthocyanidins and Leucoanthocya...mentioning

confidence: 99%

“…Biosynthesis of the naphthoquinone shikonin (141) in Lithospermum erythrorhizon is known to proceed via alkylation of 4-hydroxybenzoic acid with geranyl diphosphate (see ref. 1). As part of this sequence, a prenyltransferase [E.C.…”

Section: Quinonesmentioning

confidence: 99%