Antibiotic DE-3936, a polyether antibiotic identical with lonomycin. Taxonomy, fermentation, isolation and characterization.

Ohshima, Masayuki; Ishizaki, Noboru; Abe, Kimihiko; Ukawa, Masufumi; Marumoto, Yasumasa; Nakatsuka, Kazunobu; Horiuchi, Tadashi; Tonooka, Yasuaki; Yoshino, Shuichiro; Kanda, Nobuo

doi:10.7164/antibiotics.29.354

Cited by 9 publications

(4 citation statements)

References 13 publications

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“…Alternative modes of condensation might lead to the caerulomycins or siderochelin. Proferrorosamine, which as neopurpuratin has recently been discovered as a product of Srreptomyces purpuratus ( 19), might be similarly derived.…”

Section: Discussionmentioning

confidence: 99%

The biosynthesis of caerulomycins in Streptomyces caeruleus. Isolation of a new caerulomycin and incorporation of picolinic acid and glycerol into caerulomycin A

Vining¹,

McInnes²,

Mcculloch³

et al. 1988

Can. J. Chem.

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Oxidation with permanganate of caerulomycin A labeled biosynthetically from [U-14C]lysine in cultures of Streptomyces caeruleus yielded picolinic acid with the same specific activity as the antibiotic. [3H]Picolinic acid was incorporated into caerulomycin A with high efficiency and the label was also found exclusively in picolinic acid after oxidation, implicating free picolinic acid as an intermediate in the pathway from lysine. The substituted pyridyl ring of caerulomycin was labeled by [2-13C, 1,3-14C]glycerol. 13C nuclear magnetic resonance analysis located the 13C predominantly at C-6, suggesting that C-5, C-6, and C-7 were derived from glycerol as an intact three-carbon precursor. Since no incorporation of [1-13C]glyceric acid was detected and [3-13C, 3-14C]methylglyoxal labeled the antibiotic only marginally, these compounds are probably not biosynthetic intermediates en route from glycerol. A new caerulomycin possessing an aldehyde in place of the aldoxime substituent at C-6 was isolated from culture broths and is postulated to be a late intermediate in the formation of caerulomycin A.

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Section: Discussionmentioning

confidence: 99%

The biosynthesis of caerulomycins in Streptomyces caeruleus. Isolation of a new caerulomycin and incorporation of picolinic acid and glycerol into caerulomycin A

Vining¹,

McInnes²,

Mcculloch³

et al. 1988

Can. J. Chem.

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“…An iron(II)-containing pigment (neopurpuratin) isolated from bacterial culture was shown to contain iron(II) associated with the d -pyrimine ligand …”

Section: B Iron Complexes With Non-macrocyclic Polydentate Ligandsmentioning

confidence: 99%

“…An iron(II)-containing pigment (neopurpuratin) isolated from bacterial culture was shown to contain iron(II) associated with the D-pyrimine ligand. 120 Solution mixtures of this potential ligand with iron-(II) (3:1 [L]/[Fe]) have been claimed to possess SOD activity based on the indirect ferricytochrome c assay, but no characterization of the solution species nor isolation of an pure iron complex were reported. 121 A number of Fe(III) complexes with tripodal ligands favoring trigonal-bipyramidal coordination modes have been synthesized and been claimed to show SOD-like reactivity with superoxide anion, as shown by electrochemical studies.…”

Section: B Iron Complexes With Non-macrocyclic Polydentate Ligandsmentioning

confidence: 99%

Functional Mimics of Superoxide Dismutase Enzymes as Therapeutic Agents

Riley¹

1999

Chem. Rev.

415

261

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“…751 by Ohshima et aI. 1 ) Since this compound, which exhibited low toxicity to several species of rodent, was presumed to be useful as a food-coloring agent,2) its structure was investigated, established, and found to contain an iron atom. This paper describes the structural characterization of NP.…”

Section: Received January 21 1985mentioning

confidence: 99%