&amp;#x201C;Whole Cell&amp;#x201D; - Matrix-Assisted Laser Desorption Ionization-Time of Flight- Mass Spectrometry, an Emerging Technique for Efficient Screening of Biocombinatorial Libraries of Natural Compounds - Present State of Research

Vater, Joachim; Gao, Xuewen; Hitzeroth, Gabriele; Wilde, Christopher; Franke, P.

doi:10.2174/138620703106298725

Cited by 42 publications

(50 citation statements)

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“…Fusaricidins are protonated preferentially at the guanidine group. Therefore, precursor ions for mass spectrometric sequencing are predominantly available in protonated form in contrast to many other cyclic lipopeptides, such as the surfactins, fengycins, and iturins [37,38] with a neutral fatty acid side chain, which mainly appear as the alkali adducts when investigated by MALDI-TOF MS. The intensities of the protonated precursor ions of fusaricidins are 10-to 100-fold higher than their corresponding alkali counterparts.…”

Section: Structural Characterization Of Fusaricidins From Lift-maldi-mentioning

confidence: 99%

“…This finding is in contrast to many other lipopeptides reported in the literature, where the fatty acid part is a major target of structural variation. Prominent examples are the surfactins, iturins, and fengycins produced by numerous B. subtilis and B. amyloliquefaciens strains [37,38]. From our mass spectrometric sequence analysis, we classified the fusaricidins into three main families (series 1-3 in Table 2).…”

Section: Classification Of Fusaricidins Into Four Familiesmentioning

confidence: 99%

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Characterization of Novel Fusaricidins Produced by Paenibacillus polymyxa-M1 Using MALDI-TOF Mass Spectrometry

Vater

Niu

Dietel³

et al. 2015

J. Am. Soc. Mass Spectrom.

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Abstract. Paenibacillus polymyxa-M1 is a potent producer of bioactive compounds, such as lipopeptides, polyketides, and lantibiotics of biotechnological and medical interest. Genome sequencing revealed nine gene clusters for nonribosomal biosynthesis of such agents. Here we report on the investigation of the fusaricidins, a complex of cyclic lipopeptides containing 15-guanidino-3-hydroxypentadecanoic acid (GHPD) as fatty acid component by matrix-assisted laser-desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). More than 20 variants of these compounds were detected and characterized in detail. Mass spectrometric sequence analysis was performed by MALDI-LIFT-TOF/TOF fragment analysis. The obtained product ion spectra show a specific processing in the fatty acid part. GHPD is cleaved between the α-and ß-position yielding two fragments a and b, one bearing the end-standing guanidine group and another one comprising the residual two C-atoms of GHPD with the attached peptide moiety. The complete sequence of all fusaricidins was derived from sets of b n -and y n -ions. The fusaricidin complex can be divided into four lipopeptide families, three of them showing variations of the amino acid in position 3, Val or Ile for the first and Tyr or Phe for families 2 and 3, respectively. A collection of novel fusaricidins was detected differing from those of families 1-3 by an additional residue of 71 Da (family 4). LIFT-TOF/TOF fragment spectra of these species imply that in their peptide moiety, an Ala-residue is attached by an ester bond to the free hydroxyl group of Thr 4 . More than 10 novel fusaricidins were characterized mass spectrometrically.

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Section: Structural Characterization Of Fusaricidins From Lift-maldi-mentioning

confidence: 99%

Section: Classification Of Fusaricidins Into Four Familiesmentioning

confidence: 99%

Characterization of Novel Fusaricidins Produced by Paenibacillus polymyxa-M1 Using MALDI-TOF Mass Spectrometry

Vater

Niu

Dietel³

et al. 2015

J. Am. Soc. Mass Spectrom.

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“…1 a, b). The mass peaks at m/z = 1,032, 1,046 and 1,060 represent the protonated forms of C14-16 bacillomycin D, and those at m/z = 1,068, 1,082, 1,096 and 1,112 correspond to C15-17 bacillomycin D adducts with alkali metal ions, respectively; the mass peaks between m/z = 1,449 and 1,558 indicated B. amyloliquefaciens C06 also a producer of fengycin [Vater et al, 2002[Vater et al, , 2003. Fig.…”

Section: Ms Identification Of the Lipopeptides Of B Amyloliquefacienmentioning

confidence: 99%

“…To characterize the lipopeptides produced by B. amyloliquefaciens C06, the cell-free filtrate extracts of B. amyloliquefaciens C06 were analyzed by MALDI-TOF-MS as described previously [Vater et al, 2002[Vater et al, , 2003. MALDI-TOF mass spectra were recorded by using a Bruker Daltonik Reflex MALDI-TOF instrument containing a 337-nm nitrogen laser for desorption and ionization.…”

Section: Maldi-tof Ms Analysismentioning

confidence: 99%

Functions of Lipopeptides Bacillomycin D and Fengycin in Antagonism of <i>Bacillus amyloliquefaciens</i> C06 towards <i>Monilinia fructicola</i>

Liu¹,

Zhou

et al. 2011

Microb Physiol

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In previous studies, Bacillus amyloliquefaciens C06 has been proven to be effective in controlling brown rot of stone fruit caused by Monilinia fructicola. When tested in vitro, cell-free filtrate of B. amyloliquefaciens C06 significantly inhibited mycelial growth and conidial germination of the fungal pathogen. This study aimed to determine the role of the antifungal compound(s) in the cell-free filtrate of B. amyloliquefaciens C06 by an approach combining a DNA-based suppression subtractive hybridization (SSH) method with MALDI-TOF-MS analysis. It was demonstrated that B. amyloliquefaciens C06 harbored two genes, bmyC and fenD, involved in biosynthesis of bacillomycin D and fengycin, two lipopeptides belonging to the iturin and fengycin family, respectively. To determine the roles of bacillomycin D and fengycin of B. amyloliquefaciens C06 in suppressing M. fructicola, the mutants of B. amyloliquefaciens C06 deficient in producing bacillomy- cin D, fengycin or both were constructed, and evaluated in vitro together with the wild-type B. amyloliquefaciens C06. The results indicated that bacillomycin D and fengycin jointly contributed to the inhibition of conidial germination of M. fructicola, and fengycin played a major role in suppressing mycelial growth of the fungal pathogen.

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“…In a previous contribution (20), we have reported that B. amyloliquefaciens FZB 42 is a producer of three families of lipopeptides, surfactins, bacillomycins D, and fengycins, which are well-known secondary metabolites with mainly antifungal activity. They are also produced by numerous B. subtilis strains (48). Furthermore, three giant gene clusters containing genes with homology to polyketide synthase (PKS) genes of modular organization were identified but not assigned functional roles.…”

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confidence: 99%

Structural and Functional Characterization of Three Polyketide Synthase Gene Clusters in Bacillus amyloliquefaciens FZB 42

et al. 2006

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Although bacterial polyketides are of considerable biomedical interest, the molecular biology of polyketide biosynthesis in Bacillus spp., one of the richest bacterial sources of bioactive natural products, remains largely unexplored. Here we assign for the first time complete polyketide synthase (PKS) gene clusters to Bacillus antibiotics. Three giant modular PKS systems of the trans-acyltransferase type were identified in Bacillus amyloliquefaciens FZB 42. One of them, pks1, is an ortholog of the pksX operon with a previously unknown function in the sequenced model strain Bacillus subtilis 168, while the pks2 and pks3 clusters are novel gene clusters. Cassette mutagenesis combined with advanced mass spectrometric techniques such as matrixassisted laser desorption ionization-time of flight mass spectrometry and liquid chromatography-electrospray ionization mass spectrometry revealed that the pks1 (bae) and pks3 (dif) gene clusters encode the biosynthesis of the polyene antibiotics bacillaene and difficidin or oxydifficidin, respectively. In addition, B. subtilis OKB105 (pheA sfp 0 ), a transformant of the B. subtilis 168 derivative JH642, was shown to produce bacillaene, demonstrating that the pksX gene cluster directs the synthesis of that polyketide.Environmental Bacillus amyloliquefaciens strain FZB 42 is distinguished from the domesticated model organism Bacillus subtilis 168 (23) by several features important for rhizosphere competence particularly by its abilities to suppress competitive organisms present in the plant rhizosphere (17, 21) and to promote plant growth (16). In a previous contribution (20), we have reported that B. amyloliquefaciens FZB 42 is a producer of three families of lipopeptides, surfactins, bacillomycins D, and fengycins, which are well-known secondary metabolites with mainly antifungal activity. They are also produced by numerous B. subtilis strains (48). Furthermore, three giant gene clusters containing genes with homology to polyketide synthase (PKS) genes of modular organization were identified but not assigned functional roles. Mutants of FZB 42 deficient in the synthesis of cyclic lipopeptides were unable to suppress phytopathogenic fungi but still retained their antibacterial potency.Polyketides belong to a large family of secondary metabolites that include many bioactive compounds with antibacterial, immunosuppressive, antitumor, or other physiologically relevant bioactivities. Their biosynthesis is accomplished by stepwise decarboxylative Claisen condensations between the extender unit and the growing polyketide chain, generating enzyme-bound ␤-ketoacyl intermediates. Before a subsequent round of chain extension, a variable set of modifying enzymes can locally introduce structural variety. Similar to the nonribosomal synthesis of peptides, the PKS multienzyme system uses acyl carrier proteins (ACPs) that are posttranslationally modified with the 4Ј-phosphopantetheine prosthetic group to channel the growing polyketide intermediate during elongation processes (3). Type I PKSs...

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“Whole Cell” - Matrix-Assisted Laser Desorption Ionization-Time of Flight- Mass Spectrometry, an Emerging Technique for Efficient Screening of Biocombinatorial Libraries of Natural Compounds - Present State of Research

Cited by 42 publications

References 0 publications

Characterization of Novel Fusaricidins Produced by Paenibacillus polymyxa-M1 Using MALDI-TOF Mass Spectrometry

Characterization of Novel Fusaricidins Produced by Paenibacillus polymyxa-M1 Using MALDI-TOF Mass Spectrometry

Functions of Lipopeptides Bacillomycin D and Fengycin in Antagonism of <i>Bacillus amyloliquefaciens</i> C06 towards <i>Monilinia fructicola</i>

Structural and Functional Characterization of Three Polyketide Synthase Gene Clusters in Bacillus amyloliquefaciens FZB 42

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