Spermidine as a potential biosynthetic precursor to the 1,5‐diazabicyclo[4:3:0]nonene residue in the efrapeptins

Uma, M.; Balaram, Padmanabhan; Sudha, Rajamani

doi:10.1034/j.1399-3011.2001.00915.x

Cited by 8 publications

(4 citation statements)

References 19 publications

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“…From this observation, the authors concluded that elvapeptins may contain a C-terminal spermidine residue that might also be converted to the amine residue of efrapeptins in vivo [50].…”

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confidence: 98%

New Sequences, Constituents, and Producers of Peptaibiotics: An Updated Review

Degenkolb

Kirschbaum

Brückner

2007

Chemistry & Biodiversity

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To date, 18 genera of imperfect and ascomycetous fungi have been recognized to produce ca. 700 individual sequences of peptaibiotics. These are linear polypeptide antibiotics which i) have a molecular weight between 500 and 2,200 Dalton, thus containing 5-21 residues; ii) show a high content of alpha-aminoisobutyric acid; iii) are characterized by the presence of other nonproteinogenic amino acids and/or lipoamino acids; iv) possess an acylated N-terminus, and v) have a C-terminal residue that, in most of them, consists of a free or acetylated amide-bonded 1,2-amino alcohol, but might also be an amine, amide, free amino acid, 2,5-dioxopiperazine, or sugar alcohol. From April 2003 until present, ca. 300 new individual sequences of peptaibiotics have been published in the literature, but most of them have not yet been included in databases. To summarize these new sequences and novel constituents, as well as to introduce fungal species hitherto unknown as producers of peptaibiotics, the relevant literature is reviewed. Furthermore, ecophysiological and taxonomic aspects of the producing fungi are discussed.

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“…From this observation, the authors concluded that elvapeptins may contain a C-terminal spermidine residue that might also be converted to the amine residue of efrapeptins in vivo [50].…”

mentioning

confidence: 98%

New Sequences, Constituents, and Producers of Peptaibiotics: An Updated Review

Degenkolb

Kirschbaum

Brückner

2007

Chemistry & Biodiversity

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“…To clarify the biosynthetic relationship between efra-and elvapeptins (ELV) that have been obtained as co-metabolites from Tolypocladium inflatum IMI 202309 [49], a study was conducted which demonstrated the in vitro conversion of elvapeptins to efrapeptins by oxidative cyclization with CuCl/pyridine. From this observation, the authors concluded that elvapeptins may contain a C-terminal spermidine residue that might also be converted to the amine residue of efrapeptins in vivo [50].…”

Section: 2mentioning

confidence: 99%

New Sequences, Constituents, and Producers of Peptaibiotics: An Update Review

2007

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“…[2] The absolute configuration of Iva as l ((S)-2-Amino-2-methylbutanoic acid) was confirmed by X-ray analysis on the basis of the relative stereochemistry the C-terminal dipeptide LeuIva.…”

Section: Introductionmentioning

confidence: 96%

Synthesis and Conformational Analysis of Efrapeptins

Weigelt

Huber

Hofmann

et al. 2011

Chemistry A European J

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The efrapeptin family of peptide antibiotics produced by the fungus Tolypocladium niveum, and the neo-efrapeptins from the fungus Geotrichum candidumare inhibitors of F(1)-ATPase with promising antitumor, antimalaria, and insecticidal activity. They are rich in C(α)-dialkyl amino acids (Aib, Iva, Acc) and contain one β-alanine and several pipecolic acid residues. The C-terminus bears an unusual heterocyclic cationic cap. The efrapeptins C-G and three analogues of efrapeptin C were synthesized using α-azido carboxylic acids as masked amino acid derivatives. All compounds display inhibitory activity toward F(1)-ATPase. The conformation in solution of the peptides was investigated with electronic CD spectroscopy, FT-IR spectroscopy, and VCD spectroscopy. All efrapeptins and most efrapeptin analogues were shown to adopt helical conformations in solution. In the case of efrapeptin C, VCD spectra proved that a 3(10)-helix prevails. In addition, efrapeptin C was conformationally studied in detail with NMR and molecular modeling. Besides NOE distance restraints, residual dipolar couplings (RDC) observed upon partial alignment with stretched PDMS gels were used for the conformational analysis and confirmed the 3(10)-helical conformation.

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Spermidine as a potential biosynthetic precursor to the 1,5‐diazabicyclo[4:3:0]nonene residue in the efrapeptins

Cited by 8 publications

References 19 publications

New Sequences, Constituents, and Producers of Peptaibiotics: An Updated Review

New Sequences, Constituents, and Producers of Peptaibiotics: An Updated Review

New Sequences, Constituents, and Producers of Peptaibiotics: An Update Review

Synthesis and Conformational Analysis of Efrapeptins

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