Studies directed towards the biosynthesis of the C7N-unit of rifamycin B: Incorporation of (14C(G))quinic acid and (1,2-13C2)glycerol.

Meier, Rose-Marie; Tamm, Christoph

doi:10.7164/antibiotics.45.400

Cited by 8 publications

(4 citation statements)

References 32 publications

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“…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. The cells of the rifamycin producer Amycolatopsis mediterranei are indeed impermeable for shikimic acid.…”

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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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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“…Feeding experiments with a variety of labeled precursors 5-7 and genetic experiments 8 have demonstrated the shikimate pathway origin of the mC 7 N unit. However, all attempts to obtain incorporation of labeled shikimic acid (SA + ), 5a,,7b, quinic acid (QA), or 3-dehydroquinic acid (DHQ) 7b into the mC 7 N unit were unsuccessful. The nonincorporation of shikimate pathway intermediates could be due to impermeability of the cell membranes of the producing organisms to these compounds, demonstrated for SA in the rifamycin-producer, Amycolatopsis mediterranei ,8c or could indicate that the biosynthesis of the mC 7 N unit branches off from the shikimate pathway at an earlier stage.…”

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confidence: 99%

Biosynthesis of 3-Amino-5-hydroxybenzoic Acid, the Precursor of mC₇N Units in Ansamycin Antibiotics

et al. 1996

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The biosynthetic pathway of 3-amino-5-hydroxybenzoic acid (AHBA) formation was studied with cell-free extracts from the rifamycin B producer, Amycolatopsis mediterranei S699, and the ansatrienin A producer, Streptomyces collinus Tü1892. Phosphoenolpyruvate (PEP) plus erythrose 4-phosphate (E4P) gave AHBA in low but nevertheless significant (6%) yield. 3,4-Dideoxy-4-amino-d-arabino-heptulosonic acid 7-phosphate (aminoDAHP) was converted efficiently into AHBA (45%), as were 5-deoxy-5-amino-3-dehydroquinic acid (aminoDHQ, 41%) and 5-deoxy-5-amino-3-dehydroshikimic acid (aminoDHS, 95%). On the other hand, the normal shikimate pathway intermediate, 3-deoxy-d-arabino-heptulosonic acid 7-phosphate (DAHP) did not give rise to AHBA under these conditions. AminoDAHP (9%) was produced by incubation of [14C]PEP and E4P, but not of [14C]DAHP, with the cell-free extracts. The results demonstrate the operation of a new variant of the shikimate pathway in the formation of the mC7N units of ansamycin, and presumably also mitomycin, antibiotics which leads from PEP, E4P, and a nitrogen source directly to aminoDAHP and then via aminoDHQ and aminoDHS to AHBA.

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“…Work-up and purification of the 2.30 g crude extract using various chromatographic techniques (Figure 2) led to the isolation of five new compounds including pyramidamycins A-D ( 2 ~ 5 ) and 3-hydroxyquinoline-2-carboxamide ( 6 ), all five possessing an amide group (-CONH 2 ). In addition, the five known compounds 2-aminobenzamide (anthranilamide, 1 ), 15,16 4′,7-dihydroxyisoflavanone (daidzein, 7 ), 17,18 2′-deoxy-thymidine, 19 2′-deoxy-uridine 20 and adenosine, 19,21,22 were also isolated and characterized.…”

Section: Resultsmentioning

confidence: 99%

Pyramidamycins A-D and 3-hydroxyquinoline-2-carboxamide; cytotoxic benzamides from Streptomyces sp. DGC1

et al. 2012

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Four new benzamides, pyramidamycins A-D (2–5) along with the new natural 3-hydroxyquinoline-2-carboxamide (6) were isolated from the crude extract of Streptomyces sp. DGC1. Additionally, five other known compounds namely 2-aminobenzamide (anthranilamide) (1), 4′,7-dihydroxyisoflavanone (7), 2′-deoxy-thymidine, 2′-deoxy-uridine and adenosine were also isolated and identified. The structures of the new compounds 2–6 were elucidated by 1D and 2D NMR studies along with HRMS analyses. The isolated compounds 1–6 contained the same amide side chain. The isolated compounds 1–7 were biologically evaluated in comparison with landomycin A against a prostate cancer cell line (PC3) and non small cell lung cancer cell line (H460) for 48 hrs and against several bacterialstrains. Pyramidamycin C (4) was the most active compound against both PC3 and H460 cell lines (GI50 = 2.473 μM and GI50 = 7.339 μM, respectively). Benzamides (1–3) demonstrated inhibitory activity against Kocuria rosea B-1106 (a diameter halo of 13±2 mm for 1; 10±2 mm for 2 and 3). Compound 6 was slightly active against both Escherichia coli DH5α and Micrococcus luteus NRRL B-2618 (diameter halos 8±2 mm and 9±2 mm, respectively). Taxonomically, the amplified 500 bp 16S rRNA fragment of the Streptomyces sp. DGC1 had 99% identity (BLAST search) to the 16S rRNA gene of Streptomyces atrovirens strain NRRL B-16357.

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Studies directed towards the biosynthesis of the C7N-unit of rifamycin B: Incorporation of (14C(G))quinic acid and (1,2-13C2)glycerol.

Cited by 8 publications

References 32 publications

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

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

Biosynthesis of 3-Amino-5-hydroxybenzoic Acid, the Precursor of mC₇N Units in Ansamycin Antibiotics

Pyramidamycins A-D and 3-hydroxyquinoline-2-carboxamide; cytotoxic benzamides from Streptomyces sp. DGC1

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Studies directed towards the biosynthesis of the C7N-unit of rifamycin B: Incorporation of (14C(G))quinic acid and (1,2-13C2)glycerol.

Cited by 8 publications

References 32 publications

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

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

Biosynthesis of 3-Amino-5-hydroxybenzoic Acid, the Precursor of mC7N Units in Ansamycin Antibiotics

Pyramidamycins A-D and 3-hydroxyquinoline-2-carboxamide; cytotoxic benzamides from Streptomyces sp. DGC1

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Biosynthesis of 3-Amino-5-hydroxybenzoic Acid, the Precursor of mC₇N Units in Ansamycin Antibiotics