Structure Elucidation of the Peptide Antibiotics Herbicolin A and B

Aydin, Mitat; Lucht, Niklas; König, Wilfried Α.; Lupp, R.; Jung, Günther; Winkelmann, G.

doi:10.1002/jlac.198519851117

Cited by 60 publications

(21 citation statements)

References 33 publications

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“…Because of the obvious relationship of epidennin with nisin, we looked for the presence of a$-unsaturated amino acids, and found 2,3-dehydro-2-aminobutyric acid. This amino acid has also been found recently in the hydrogenated new glycolipononadepsipeptide antibiotic herbicolin A [25]. The dehydroaminobutyric acid residue present in native epidermin, nisin and herbicolin A cannot be detected by common amino acid analysis, because of its conversion to the characteristically smelling (soup flavour) 2-oxobutyric acid during acid hydrolysis.…”

Section: Amino Acid Compositionmentioning

confidence: 86%

Epidermin: sequencing of a heterodet tetracyclic 21‐peptide amide antibiotic

Allgaier

Jung

Werner

et al. 1986

European Journal of Biochemistry

244

109

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Epidermin is a large peptide antibiotic, which is synthesized in the ribosome via a precursor protein, followed by enzymatic modifications. It was isolated from the culture filtrate of Staphylococcus epidermidis TU 3298 by adsorption on Amberlite XAD-8. The basic heneicosapeptide amide was chromatographed on Sephadex LH-20 and purified to homogeneity via multiplicative counter-current distributions in one acidic and one neutral system. Tryptic digestion gave the soluble N-terminal fragment epidermin-(I -13)-peptide (Pl) and the insoluble Cterminal fragment 2-oxobutyryl-epidermin-(l5 -21)-peptide amide (P2), each possessing two sulfide ring systems. The heterodetic rings consisted of meso-lanthionine and (2S,3S,6R)-3-methyllanthionine (Pl), meso-lanthionine and C-terminally the new amino acid S-(2-aminovinyl)-~-cysteine (P2). The complex sequence was elucidated via a combination of desulfurization with Raney nickel, enzymatic and acidolytic degradations, gas-phase sequencing, fast-atom bombardment and field-desorption mass spectrometry and NMR spectroscopy.

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Section: Amino Acid Compositionmentioning

confidence: 86%

Epidermin: sequencing of a heterodet tetracyclic 21‐peptide amide antibiotic

Allgaier

Jung

Werner

et al. 1986

European Journal of Biochemistry

244

109

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“…Apart from the xanthomonads, only one strain of E. herbicola produced a substance which behaved as DSF, among the range of bacteria tested (Table 2). E. herbicola is known to produce an antibiotic containing a hydroxy fatty-acid moiety (Aydin et al, 1985), and it is possible that DSF activity is related to production of this substance. Further study of DSF and other regulatory mechanisms should advance our understanding of the adaptation of bacteria to parasitic life within plants.…”

Section: Discussionmentioning

confidence: 99%

A novel regulatory system required for pathogenicity of Xanthomonas campestris is mediated by a small diffusible signal molecule

Barber

Tang²,

Feng³

et al. 1997

Molecular Microbiology

468

512

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SummaryMutations in the seven clustered rpf genes cause downregulated synthesis of extracellular enzymes and reduced virulence of Xanthomonas campestris pathovar campestris (Xcc). The phenotype of mutants in one of the genes, rpfF, can be restored by a diffusible extracellular factor (DSF) produced by all Xcc strains tested, apart from rpfF and rpfB mutants. DSF accumulates in early stationary phase (when synthesis of enzymes is maximal), but levels decline subsequently. Addition of DSF to exponentially-growing wild-type bacteria does not cause precocious enzyme synthesis. rpfB and rpfF are expressed throughout growth, but the rate increases in early stationary phase. RpfB is predicted to be a long-chain fatty acyl CoA ligase, and RpfF shows some relatedness to enoyl CoA hydratases. The properties of DSF suggest that it may be a fatty-acid derivative, and certain lipid preparations possess DSF activity at higher concentrations. These include lipid extracts and acid-hydrolysed lipopolysaccharide and lipid A from Xcc, and purified dodecanoic and hydroxydodecanoic acid. DSF production is confined to certain xanthomonads. We propose a model for the DSF system, which represents a novel mechanism for regulating virulence factor synthesis in response to physiological or environmental changes.

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“…In. addition to the counter-current distribution method described previously (Aydin et al 1985), pure herbicolin It has been mentioned earlier that lowering the cultivation temperature to 16°C had a positive effect on the purification procedures. As seen in Fig.…”

Section: Fermentationmentioning

confidence: 99%

Fermentation and isolation of herbicolin A, a peptide antibiotic produced byErwinia herbicola strain A 111

Greiner

Winkelmann

1991

Appl Microbiol Biotechnol

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Erwinia herbicola (Enterobacter agglomerans), belonging to the Enterobacteriaceae, produces the lipopeptide antibiotics herbicolin A and B, which are active against sterol-containing fungi. Fermentation of these antibiotics was performed in 20-l stirred glass fermentors in a batch process. Best yields of antibiotic production were found at low cultivation temperatures in a TRIS-buffered chemically defined medium. Under these conditions the amount of impurities aggravating the purification was minimized. Isolation was performed by adsorption, and gel and ion exchange chromatographic techniques. In a final purification step preparative high performance liquid chromatography (PHPLC) yielded pure herbicolin A.

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Structure Elucidation of the Peptide Antibiotics Herbicolin A and B

Cited by 60 publications

References 33 publications

Epidermin: sequencing of a heterodet tetracyclic 21‐peptide amide antibiotic

Epidermin: sequencing of a heterodet tetracyclic 21‐peptide amide antibiotic

A novel regulatory system required for pathogenicity of Xanthomonas campestris is mediated by a small diffusible signal molecule

Fermentation and isolation of herbicolin A, a peptide antibiotic produced byErwinia herbicola strain A 111

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