Ampullosporin A
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| Category | Antibiotics |
| Catalog number | BBF-00451 |
| CAS | 197960-94-4 |
| Molecular Weight | 1622.94 |
| Molecular Formula | C77H127N19O19 |
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Description
Ampullosporin A is produced by the strain of Sepedonium ampullosporum HKI-0053. Its antibacterial spectrum is narrow. The anti-staphylococcus aureus GS511, Bacillus subtilis, Pseudomonas aeruginosa K599/WT, Escherichia coli SG458, Ocher sporococcus SBUG 549 and Deep red yeast and other bacteria and fungi had only moderate intensity activity, and had no effect on other yeast and candida albicans. It can cause Phoma destructiva to form pigment. Its content is greater than 1mg/kg, which can cause hypothermia and reduce automatic exercise in rats.
Specification
| Synonyms | N-Acetyl-L-tryptophyl-L-alanyl-2-methylalanyl-2-methylalanyl-L-leucyl-2-methylalanyl-L-glutaminyl-2-methylalanyl-2-methylalanyl-2-methylalanyl-L-glutaminyl-L-leucyl-2-methylalanyl-N1-[(1S)-1-(hydroxymethyl)-3-methylbutyl]-L-glutamamide |
| IUPAC Name | (S)-2-((11S,17S,26S,29S)-29-((1H-indol-3-yl)methyl)-11-(3-amino-3-oxopropyl)-17-isobutyl-2,2,5,5,8,8,14,14,20,20,23,23,26-tridecamethyl-4,7,10,13,16,19,22,25,28,31-decaoxo-3,6,9,12,15,18,21,24,27,30-decaazadotriacontanamido)-N1-((S)-1-((1-(((S)-5-amino-1-(((S)-1-hydroxy-4-methylpentan-2-yl)amino)-1,5-dioxopentan-2-yl)amino)-2-methyl-1-oxopropan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)pentanediamide |
Properties
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 1894.6±65.0 °C |
| Density | 1.216±0.06 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1. Synthesis and conformational properties of a TOAC doubly spin-labeled analog of the medium-length, membrane active peptaibiotic ampullosporin A as revealed by CD, fluorescence, and EPR spectroscopies
Alexander D Milov, Yuri D Tsvetkov, Marco Bortolus, Anna Lisa Maniero, Marina Gobbo, Claudio Toniolo, Fernando Formaggio Biopolymers. 2014 Jan;102(1):40-8. doi: 10.1002/bip.22362.
We describe the challenging solid-phase synthesis of the medium-length (14 amino-acid residues) peptaibiotic ampullosporin A, originally extracted from the fungus Sepedonium ampullosporum, and an analog doubly spin labeled (at positions 3 and 13) with the stable nitroxyl free-radical 4-amino-1-oxyl-2,2,6,6-tetramethylpiperidine-4-carboxylic acid (TOAC). The results of a circular dichrosim investigation in methanol strongly support the view that both peptides are essentially right-handed helical, in particular endowed with a large population of α-helical conformers. We also observed a significant quenching effect from the TOAC(3) nitroxyl radical on the fluorescence of Trp(1), compatible with that expected when both residues are closely located on the same helix segment. Combined continuous wave and pulsed electron-electron double resonance electron paramagnetic resonance methodologies converge on the conclusion obtained from the other aforementioned spectroscopies, namely, that the [TOAC(3,13)] ampullosporin A analog is mostly folded in the α-helical conformation. A liposome leakage assay demonstrated that the membrane-modifying properties of this bis-labeled analog are remarkable and even slightly superior to those of the natural peptaibiotic itself.
2. Correction: An EPR study of ampullosporin A, a medium-length peptaibiotic, in bicelles and vesicles
Marco Bortolus, Annalisa Dalzini, Fernando Formaggio, Claudio Toniolo, Marina Gobbo, Anna Lisa Maniero Phys Chem Chem Phys. 2019 Oct 24;21(41):23217. doi: 10.1039/c9cp90246e.
Correction for 'An EPR study of ampullosporin A, a medium-length peptaibiotic, in bicelles and vesicles' by Marco Bortolus et al., Phys. Chem. Chem. Phys., 2016, 18, 749-760.
3. An EPR study of ampullosporin A, a medium-length peptaibiotic, in bicelles and vesicles
Marco Bortolus, Annalisa Dalzini, Fernando Formaggio, Claudio Toniolo, Marina Gobbo, Anna Lisa Maniero Phys Chem Chem Phys. 2016 Jan 14;18(2):749-60. doi: 10.1039/c5cp04136h.
Ampullosporin A is a medium-length (14-amino acid long) hydrophobic peptide of the peptaibol family. In this work, electron paramagnetic resonance and circular dichroism spectroscopies were applied to study the interaction of synthetic ampullosporin A and three spin-labeled analogs with small unilamellar vesicles and bicelles. Zwitterionic vesicles were used to investigate the conformation and the penetration depth of the peptide at room temperature. Bicelles were employed in combination with EPR spectroscopy to study the order, dynamics, orientation, aggregation and the 3D-structure of the peptide at near physiological temperature. In the membrane, the peptide adopts a helical structure that changes in nature depending on the thickness of the membrane-mimetic system, from mostly α-helical in vesicles to a more elongated helix in bicelles, suggesting an increase in the 310-helical content. The orientation assumed by the peptide also shows a dependence on the membrane-mimetic system: in bicelles, ampullosporin A has a transmembrane orientation at a peptide-to-lipid (P : L) ratio of 1 : 100 and higher, while in vesicles it undergoes a transition from a parallel to a transmembrane orientation as a function of the P : L ratio. In bicelles, the peptide was found to be monomeric at a P : L ratio of 1 : 25 and lower. Overall, the comparison of the results obtained in the two membrane-mimetic systems showed that ampullosporin A has a rather flexible structure that readily adapts to the bilayer thickness.
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Bio Calculators
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