Kalafungin. II. Chemical transformations and the absolute configuration.

Hoeksema, Herman; Krueger, William C.

doi:10.7164/antibiotics.29.704

Cited by 76 publications

(30 citation statements)

References 9 publications

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“…1) was elucidated by Brockmann et al (1966). Actinorhodin is now considered to be a member of a chemically related group of antibiotics called isochromanequinones , which also includes kalafungin (Hoeksema & Krueger, 1976), nanaomycins (Tanaka et al, 1975;amura et al, 1976), the griseusins (Tsuji et al, 1976), granaticin (Carbaz et al, 1957 and the naphthocyclinones .…”

Section: Introductionmentioning

confidence: 99%

Genetics of Actinorhodin Biosynthesis by Streptomyces coelicolor A3(2)

Rudd

Hopwood

1979

Journal of General Microbiology

192

117

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35 ~ ~~A series of 76 mutants of Streptomyces coelicolor A3(2) specifically blocked in the synthesis of the binaphthoquinone antibiotic actinorhodin were classified into seven phenotypic classes on the basis of antibiotic activity, accumulation of pigmented precursors or shunt products of actinorhodin biosynthesis, and cosynthesis of actinorhodin in pairwise combinations of mutants. The polarity of cosynthetic reactions, and other phenotypic properties, allowed six of the mutant classes to be arranged in the most probable linear sequence of biosynthetic blocks. One member of each mutant class was mapped unambiguously to the chromosomal linkage map in the short segment between the hisD and guaA loci, suggesting that structural genes for actinorhodin biosynthesis may form an uninterrupted cluster of chromosomal genes.

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Section: Introductionmentioning

confidence: 99%

Genetics of Actinorhodin Biosynthesis by Streptomyces coelicolor A3(2)

Rudd

Hopwood

1979

Journal of General Microbiology

192

117

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“…Treatment with 1 N KOH (as normally used for actinorhodin isolation) caused complete degradation of ␥-actinorhodin, mainly to a single compound tentatively identified as actinorhodinic acid (Fig. 1) by comparison of 1 H NMR data with those for kalafunginic acid (23). This product shows an absorption maximum in 1 N KOH at 645 nm (646 nm in 2 N KOH) (11).…”

mentioning

confidence: 99%

“…Polyketide lactones are unstable at a high pH (12,23), degrading to a so-called acid form. Treatment with 1 N KOH (as normally used for actinorhodin isolation) caused complete degradation of ␥-actinorhodin, mainly to a single compound tentatively identified as actinorhodinic acid (Fig.…”

mentioning

confidence: 99%

Production of actinorhodin-related "blue pigments" by Streptomyces coelicolor A3(2)

et al. 1996

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The genetically well-known strain Streptomyces coelicolor A3(2) produces the pH indicator (red/blue) antibiotic actinorhodin, but not all the ''blue pigment'' produced by this strain is actinorhodin. When the organism was subjected to various nutrient limitations (ammonium, nitrate, phosphate, or trace elements), and also during growth cessation caused by a relatively low medium pH, blue pigment production was initiated but the pigment and its location varied. At pH 4.5 to 5.5, significant formation of actinorhodin occurred and was located exclusively intracellularly. At pH 6.0 to 7.5 a different blue pigment was produced intracellularly as well as extracellularly. It was purified and identified as ␥-actinorhodin (the lactone form of actinorhodin). Analysis of act mutants of S. coelicolor A3(2) confirmed that both pigments are derived from the act biosynthetic pathway. Mutants with lesions in actII-ORF2, actII-ORF3, or actVA-ORF1, previously implicated or suggested to be involved in actinorhodin export, were impaired in production of ␥-actinorhodin, suggesting that synthesis of ␥-actinorhodin from actinorhodin is coupled to its export from the cell. However, effects on the level of actinorhodin production were also found in some mutants.

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“…The known Cglycosyl BIQ compounds are based on two enantiomeric chromophores: kalafungin 14 [40][41][42] and nanaomycin D 15 [43], shown in Fig. (7).…”

Section: Benzoisochromanquinonesmentioning

confidence: 99%

Bioactive C-Glycosides from Bacterial Secondary Metabolism

Hultin

2005

CTMC

125

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C-Glycosides are commonly regarded as unusual structures, but they are far more prevalent among natural products than is imagined. This review discusses the C-glycosidic compounds produced by various bacteria, particularly the "biosynthetically talented" Streptomyces. The major structure types are presented, along with brief descriptions of the known biological and pharmacological properties of the compounds. Recent work has uncovered the genetic basis for the biosynthesis of several bacterial C-glycosides, and emphasis is placed on those cases where it has been possible to identify (at least provisionally) the C-glycosyltransferase in the pathway. Prospects for biosynthetic engineering, combinatorial biosynthesis, or glycorandomization in C-glycosidic natural products are briefly discussed.

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Kalafungin. II. Chemical transformations and the absolute configuration.

Cited by 76 publications

References 9 publications

Genetics of Actinorhodin Biosynthesis by Streptomyces coelicolor A3(2)

Genetics of Actinorhodin Biosynthesis by Streptomyces coelicolor A3(2)

Production of actinorhodin-related "blue pigments" by Streptomyces coelicolor A3(2)

Bioactive C-Glycosides from Bacterial Secondary Metabolism

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