Sequence and Conformation of Suzukacillin A

Katz, Ellen B.; Jung, Günther; Aydin, Mitat; Lucht, Niklas; König, Wilfried Α.; Ooka, Tadaaki

doi:10.1002/jlac.198519850518

Cited by 36 publications

(11 citation statements)

References 39 publications

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“…After 8 h of acidolysis, starting material 29 was no longer detectable. The data are also in good agreement with those of isolated fragments resulting from the preparative trifluoroacetolysis of the alamethicinrelated peptaibol suzukacillin [16].…”

supporting

confidence: 81%

“…Notably, bonds formed by other C(a),C(a)-dialkylated glycines, such as isovaline (Iva, 2-ethylalanine), and amino acids related to Pro, such as Hyp or Pip, show a similar cleavage behavior. However, the slow release of C-terminal Aib as well as tri-and tetrapeptides from N-acetylpeptide acids, resulting from preparative TFA scission of trichotoxin [15] and suzukacillin [16], had been recognized, indicating further cleavage preferences.…”

mentioning

confidence: 98%

“…Subsequently, analytical and preparative trifluoroacetolysis of the peptaibols trichotoxin and suzukacillin was intensively used by Jung and co-workers [15] [16]. It was shown that release of C-terminal peptides occurs, besides the fast scission of the Aib -Pro bond that is followed by cleavages of certain Aib -Aaa bonds (Aaa: Gly, Ala).…”

mentioning

confidence: 98%

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Studies on the Selective Trifluoroacetolytic Scission of Native Peptaibols and Model Peptides Using HPLC and ESI‐CID‐MS

Theis

Degenkolb

Brückner

2008

Chemistry & Biodiversity

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Representative members of a group of linear, N-acylated polypeptide antibiotics (peptaibols) containing alpha-aminoisobutyric acid (Aib) and, in part, isovaline (Iva), as well as proteinogenic amino acids and a C-terminal-bonded 2-amino alcohol, were treated with anhydrous trifluoroacetic acid (TFA) at 37 degrees for 0.5-26 h. The resulting fragments were separated by HPLC and characterized by electrospray ionization collision-induced dissociation mass spectrometry (ESI-CID-MS). The following 16-20-residue peptaibols were investigated: natural, microheterogeneous mixtures of antiamoebins and alamethicin F50, uniform paracelsin A, and synthetic trichotoxin A50/E. In the natural peptides, bonds formed between Aib (Iva) and Pro (Hyp) were rapidly and selectively cleaved within 0.5 h. Furthermore, TFA esters of the C-terminal amino alcohols were formed. Depending on time, release of C-terminal tri- and tetrapeptides as well as amino acids from the major fragments was observed. Synthetic homooligopeptides, namely Z- and Ac-(Aib)(10)-O(t)Bu and Z-(Aib)(7)-O(t)Bu, were analyzed for comparison. On treatment with TFA, a regular series of Z-(Aib)(10-5)-OH from Z-(Aib)(10)-O(t)Bu were detected within 0.5 h, and, after 3 h, release of a regular series of Z-(Aib)(7-3)-OH from Z-(Aib)(7)-O(t)Bu were observed. Moreover, concomitant release of the series of H-(Aib)(10-3)-OH from the decapeptide occurred. From these data, a repetitive cleavage mechanism via intermediate formation of C-terminal oxazolones on trifluoroacetolysis is proposed. Furthermore, their formation and stability in native peptaibols are correlated with subtle structural differences in protein amino acids linked to Aib. From the conspicuous concordance of the formation and abundance of regular series of trifluoroacetolytic fragments and of positive ions of the b-series in CID-MS, the generation of intermediate oxazolonium ions in both gas and liquid phase is concluded.

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confidence: 81%

mentioning

confidence: 98%

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Studies on the Selective Trifluoroacetolytic Scission of Native Peptaibols and Model Peptides Using HPLC and ESI‐CID‐MS

Theis

Degenkolb

Brückner

2008

Chemistry & Biodiversity

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“…The synthetic heptapeptides with the sequences of suzukacillin 14-20 (2) and alamethicin [14][15][16][17][18][19][20] (1) and the isolated natural peptides exhibit a strong negative These CD spectra seem to arise from a superposition of a 3,,-helix with an a-helix similar to the X-ray structure found in the C-terminal alamethicin segment 12-2019320).…”

Section: Uv and CD Spectramentioning

confidence: 93%

The C‐Terminal Heptapeptides of Suzukacillin A and Alamethicin F30 — Sequence, Conformation, and Synthesis

Katz¹,

Schmitt²,

Jung³

et al. 1985

Liebigs Ann. Chem.

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Suzukacillin A is a potential-dependent membrane pore-forming polypeptide antibiotic exhibiting similar properties as alamethicin in biophysical1.2) and biological3-6) experiments. The essential a-helical part of these polypeptides with its high dipole moment is responsible for potential-dependent pore formation in black lipid membranes as described by the flip-flop gating model7). On the other hand the polarity and size of the C-and N-termini determine specific characteristics such as medium pore size and stability of pore statesa.9). Thus the exact knowledge of structure/activity relations contributes considerably to a better understanding of the ionconduction properties of these linear amphiphilic polypeptides.A preliminary sequence based solely on GC-MS studies of partial fragments was published 1976 by our groups'). As alamethicin'O.'') and trichotoxin A40'2-'4) the eicosapeptide suzukacillin A belongs to the longest peptide antibiotics known and shows a characteristic natural microheterogeneity in its amino acid composition. Because of several ambiguities in the former instrumental sequencing') it was necessary to isolate and 0 VCH Verlagsgesellschaft mbH, D-6940 Weinheim, 1985

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“…20% N-terminal Ac-d-Iva in a sample of SZ-B, isolated as described above, was recognized [14] [15]. No further attempts were undertaken to structurally characterize the minor component SZ-B, whereas a general sequence and amino acid exchange positions of SZ-A could be determined [16] [17]. Recently, SZ-A was shown to be a very microheterogeneous mixture of 15 homologous and positionally isomeric icosapeptides, SZ-A1À13 2 ), all of them displaying an N-terminal pentapeptide AcAib .…”

mentioning

confidence: 99%

The Sequences of the Eleven‐Residue Peptaibiotics: Suzukacillins‐B

Röhrich

Vilcinskas

Brückner

et al. 2013

Chemistry & Biodiversity

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The filamentous fungus designated 'Trichoderma viride' strain 63 C-1 simultaneously produces suzukacillins (SZs), two microheterogeneous groups of peptaibols, under submerged culture conditions. Both groups are readily distinguishable by TLC: the major group is designated SZ-A, whereas the minor group with a higher Rf value is named SZ-B. The peptide mixture was obtained from a MeOH extract of the mycelium. SZ-B was separated from SZ-A by Sephadex LH-20 column chromatography. Although it provided one single spot on silica-gel TLC plates, 15 individual peptides could be separated by C8 reversed-phase (RP) HPLC, and their sequences were determined by HPLC/QqTOF-ESI-HRMS. Fourteen peptides exhibit the C-terminal sequence Pro(6) -Lxx-Lxx-Aib-Pro-Vxxol/Lxxol(11) , which is common for eleven-residue peptaibols. The remaining peptide is tentatively assigned as a ten-residue sequence, in which the C-terminal 1,2-amino alcohol is deleted, thus terminating in free proline. Nine of the peptides carry an Ac-Aib residue at the N-terminus, very frequently found in eleven-residue peptaibols. Four peptides comprise the rare Ac-Ala N-terminus, and for two peptides, N-terminal Ac-D-Iva residues were identified. One peptide contains a C-terminal residue of yet undetermined structure. Comparison with previously reported eleven-residue peptaibol sequences reveals that eight of the peptides represent new sequence analogs.

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Sequence and Conformation of Suzukacillin A

Cited by 36 publications

References 39 publications

Studies on the Selective Trifluoroacetolytic Scission of Native Peptaibols and Model Peptides Using HPLC and ESI‐CID‐MS

Studies on the Selective Trifluoroacetolytic Scission of Native Peptaibols and Model Peptides Using HPLC and ESI‐CID‐MS

The C‐Terminal Heptapeptides of Suzukacillin A and Alamethicin F30 — Sequence, Conformation, and Synthesis

The Sequences of the Eleven‐Residue Peptaibiotics: Suzukacillins‐B

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