Cephaibol A
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| Category | Bioactive by-products |
| Catalog number | BBF-00506 |
| CAS | |
| Molecular Weight | 1670.98 |
| Molecular Formula | C82H127N17O20 |
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Description
It is produced by the strain of Acremonium tubakii DSM 12774. It has anti-gram-positive bacterial activity, but no anti-gram-negative bacterial activity. It also has the effect of deworming and anti-ectoparasite.
Specification
| IUPAC Name | (2S)-2-[[(2S)-1-[2-[[(2S)-2-[[(2S)-2-[[2-[[2-[[2-[[2-[[2-[[(2S)-2-acetamido-3-phenylpropanoyl]amino]-2-methylpropanoyl]amino]-2-methylpropanoyl]amino]-2-methylpropanoyl]amino]-2-methylpropanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-2-methylbutanoyl]amino]-2-methylpropanoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-N-[(2S)-1-[(2S)-4-hydroxy-2-[[1-[(2S)-2-[(1-hydroxy-3-phenylpropan-2-yl)carbamoyl]pyrrolidin-1-yl]-2-methyl-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-2-methyl-1-oxobutan-2-yl]pentanediamide |
| Canonical SMILES | CCC(C)(C(=O)NC(C)(C)C(=O)N1CC(CC1C(=O)NC(CCC(=O)N)C(=O)NC(C)(CC)C(=O)N2CC(CC2C(=O)NC(C)(C)C(=O)N3CCCC3C(=O)NC(CC4=CC=CC=C4)CO)O)O)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)C(CC5=CC=CC=C5)NC(=O)C |
| InChI | InChI=1S/C82H127N17O20/c1-20-81(18,91-63(108)54(37-46(3)4)87-60(105)42-84-67(112)75(6,7)93-69(114)77(10,11)95-70(115)78(12,13)94-68(113)76(8,9)89-62(107)55(85-47(5)101)39-49-31-26-23-27-32-49)71(116)96-80(16,17)73(118)98-43-51(102)40-57(98)65(110)88-53(34-35-59(83)104)61(106)92-82(19,21-2)74(119)99-44-52(103)41-58(99)66(111)90-79(14,15)72(117)97-36-28-33-56(97)64(109)86-50(45-100)38-48-29-24-22-25-30-48/h22-27,29-32,46,50-58,100,102-103H,20-21,28,33-45H2,1-19H3,(H2,83,104)(H,84,112)(H,85,101)(H,86,109)(H,87,105)(H,88,110)(H,89,107)(H,90,111)(H,91,108)(H,92,106)(H,93,114)(H,94,113)(H,95,115)(H,96,116)/t50?,51?,52?,53-,54-,55-,56-,57-,58-,81-,82-/m0/s1 |
| InChI Key | GRLRXSCBAQPCSF-ISGRKPNRSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; parasites |
Reference Reading
1. The N-terminal nonapeptide of cephaibols A and C: a naturally occurring example of mismatched helical screw-sense control
Ugo Orcel, Matteo De Poli, Marta De Zotti, Jonathan Clayden Chemistry. 2013 Nov 25;19(48):16357-65. doi: 10.1002/chem.201302648. Epub 2013 Oct 9.
The N-terminal nonapeptide domain of the fungal nonribosomal peptide antibiotics cephaibol A and cephaibol C (AcPheAib4LeuIvaGly- Aib) is reported to adopt a right-handed helical conformation in the crystalline state. However, this conformation is at odds with the left-handed helicity observed in solution in related synthetic oligomers capped with Ac-L-PheAib4 fragments. We report the synthesis of four diastereoisomers of the cephaibol N-terminal nonapeptide, and show by NMR and CD spectroscopy that the peptide containing the chiral amino acids Phe and Leu in the naturally occurring relative configuration exists in solution as an interconverting mixture of helical screw-sense conformers. In contrast, the nonapeptide containing the unnatural relative configuration at Phe and Leu adopts a single, stable helical screw-sense, which is left handed when the N-terminal Phe residue is L and right-handed when the N-terminal Phe residue is D.
2. Cephaibols, new peptaibol antibiotics with anthelmintic properties from Acremonium tubakii DSM 12774
M Schiell, J Hofmann, M Kurz, F R Schmidt, L Vértesy, M Vogel, J Wink, G Seibert J Antibiot (Tokyo). 2001 Mar;54(3):220-33. doi: 10.7164/antibiotics.54.220.
Two groups of new peptaibol-type antibiotics termed cephaibols have been isolated from the fungus Acremonium tubakii, DSM 12774. These 16- or 17-unit straight-chain peptides, whose structures were characterized by amino acid analyses, 2-D NMR experiments, and by mass spectrometric sequencing, have a high content of the unusual amino acids aminoisobutyric acid and isovaline. The principal constituent of the novel peptaibol mixture is cephaibol A, which is formed in abundance in cultures of the wild strain. The striking biological property of cephaibol A is its pronounced anthelmintic action and activity against ectoparasites.
3. Crystal structures of cephaibols
Gábor Bunkóczi, Matthias Schiell, László Vértesy, George M Sheldrick J Pept Sci. 2003 Nov-Dec;9(11-12):745-52. doi: 10.1002/psc.496.
The crystal structures of the peptaibol antibiotics cephaibol A, cephaibol B and cephaibol C have been determined at ca. 0.9 A resolution. All three adopt a helical conformation with a sharp bend (of about 55 degrees) at the central hydroxyproline. All isovalines were found to possess the D configuration, superposition of all four models (there are two independent molecules in the cephaibol B structure) shows that the N-terminal helix is rigid and the C-terminus is flexible. There are differences in the hydrogen bonding patterns for the three structures that crystallize in different space groups despite relatively similar unit cell dimensions, but only in the case of cephaibol C does the packing emulate the formation of a membrane channel believed to be important for their biological function.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
