Bergofungin D
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00136 |
| CAS | |
| Molecular Weight | 1440.72 |
| Molecular Formula | C69H113N15O18 |
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Description
Bergofungin D is a Peptaibols compound produced by Emericellopsis donezkii HKI 0059. It has anti-fungal activity such as Sporibolomy-ces salmonicolor and PenicilltiTn fiotatum. It also moderately inhibits prolyl endopeptidase activity.
Specification
| IUPAC Name | (2S)-2-[[(2S,4R)-1-[2-[[2-[[(2S)-2-[[2-[[(2S)-2-[[2-[[2-[[(2S)-2-acetamido-3-methylbutanoyl]amino]-2-methylpropanoyl]amino]-2-methylpropanoyl]amino]-3-methylbutanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-2-methylpropanoyl]amino]-2-methylpropanoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-N-[(2S)-1-[(2S,4R)-4-hydroxy-2-[[1-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-2-methyl-1-oxobutan-2-yl]pentanediamide |
| Canonical SMILES | CCC(C)(C(=O)N1CC(CC1C(=O)NC(C)(C)C(=O)NC(CC2=CC=CC=C2)CO)O)NC(=O)C(CCC(=O)N)NC(=O)C3CC(CN3C(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)C(C(C)C)NC(=O)C)O |
| InChI | InChI=1S/C69H113N15O18/c1-20-69(19,63(102)84-34-43(88)31-47(84)55(94)78-64(9,10)58(97)73-41(35-85)29-40-24-22-21-23-25-40)80-52(91)44(26-27-48(70)89)75-54(93)46-30-42(87)33-83(46)62(101)68(17,18)82-61(100)66(13,14)77-53(92)45(28-36(2)3)74-49(90)32-71-56(95)50(37(4)5)76-59(98)65(11,12)81-60(99)67(15,16)79-57(96)51(38(6)7)72-39(8)86/h21-25,36-38,41-47,50-51,85,87-88H,20,26-35H2,1-19H3,(H2,70,89)(H,71,95)(H,72,86)(H,73,97)(H,74,90)(H,75,93)(H,76,98)(H,77,92)(H,78,94)(H,79,96)(H,80,91)(H,81,99)(H,82,100)/t41-,42+,43+,44-,45-,46-,47-,50-,51-,69-/m0/s1 |
| InChI Key | TWECEMYZYGHZNE-OITGNOEESA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 252-254°C |
Reference Reading
1. How are 1,2,3-triazoles accommodated in helical secondary structures?
Khoubaib Ben Haj Salah, Sanjit Das, Nicolas Ruiz, Vanessa Andreu, Jean Martinez, Emmanuel Wenger, Muriel Amblard, Claude Didierjean, Baptiste Legrand, Nicolas Inguimbert Org Biomol Chem. 2018 May 15;16(19):3576-3583. doi: 10.1039/c8ob00686e.
1,4-Disubstituted-1,2,3-triazole (Tz) is widely used in peptides as a trans-amide bond mimic, despite having hazardous effects on the native peptide activity. The impact of amide bond substitution by Tz on peptide secondary structures is scarcely documented. We performed a Tz scan, by systematically replacing peptide bonds following the Aib residues with Tz on two model peptaibols: alamethicin F50/5 and bergofungin D, which adopt stable α- and 310 helices, respectively. We observed that the Tz insertion, whatever its position in the peptide sequences, abolished their antimicrobial activity. The structural consequences of this insertion were further investigated using CD, NMR and X-ray diffraction. Importantly, five crystal structures that were incorporated with Tz were solved, showing various degrees of alteration of the helical structures, from minor structural perturbation of the helix to partial disorder. Together, these results showed that Tz insertions impair helical secondary structures.
2. Efficient microwave-assisted one shot synthesis of peptaibols using inexpensive coupling reagents
Khoubaib Ben Haj Salah, Nicolas Inguimbert Org Lett. 2014 Mar 21;16(6):1783-5. doi: 10.1021/ol5003253. Epub 2014 Mar 12.
A diisopropylcarbodiimide/Oxyma (ethyl 2-cyano-2-(hydroxyimino)acetate) coupling cocktail was successfully incorporated into the automated microwave-assisted synthesis of two peptaibols and one analog, whose previously reported syntheses were complicated by steric hindrance. This method utilizes commercially available reagents and affords alamethicin F50/5 and bergofungin D in high yields and purities along with an appreciable reduction of synthesis time and cost when compared to previously reported methods.
3. Isovaline in naturally occurring peptides: A nondestructive methodology for configurational assignment
Marta De Zotti, Barbara Biondi, Marco Crisma, Claudia U Hjørringgaard, Albrecht Berg, Hans Brückner, Claudio Toniolo Biopolymers. 2012;98(1):36-49. doi: 10.1002/bip.21679. Epub 2011 May 17.
The nonproteinogenic, C(α)-tetrasubstituted, helicogenic, chiral α-amino acid isovaline (Iva) is remarkably spread in the biosphere. Together with its achiral, lower homolog α-aminoisobutyric acid (Aib), it represents a characteristic marker of a class of naturally occurring peptide antibiotics, for which the acronym "peptaibiotics" became established. In these peptides, Iva occurs as the (S)-(= L) or the (R)-(= D) enantiomer, but peptide sequences containing both Iva enantiomers are also common. Here, we applied our recently developed (1)H-NMR method, which enables the nondestructive assignment of the configuration of each Iva residue in a peptide of known helical screw sense, to natural and synthetic peptaibiotics. Our method proved to be generally applicable and provided evidence that, in the peptaibiotic bergofungin A, the Iva(12) configuration is (R) and not (S) as reported previously. Moreover, we extended our NMR method by including a (13)C-NMR parameter. A statistical analysis of the preferred main- and side-chain conformations of the Iva residues in peptides, performed based on their published X-ray diffraction structures, allowed us to provide a sound rationale to the NMR criteria exploited to establish the configuration of this amino acid.
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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 ╳
