Bergofungin
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| Category | Antibiotics |
| Catalog number | BBF-00133 |
| CAS | |
| Molecular Weight | 1525.82 |
| Molecular Formula | C73H120N16O19 |
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Description
Bergofungin 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
| Synonyms | Bergofungin A |
| IUPAC Name | 2-[[1-[2-[[2-[[2-[[2-[[2-[[2-[[2-[[2-[(2-acetamido-3-methylbutanoyl)amino]-2-methylpropanoyl]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-[1-[4-hydroxy-2-[[1-[(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)NC(=O)C(C(C)C)NC(=O)C)O |
| InChI | InChI=1S/C73H120N16O19/c1-22-73(21,66(108)89-36-45(93)33-49(89)57(99)82-67(9,10)60(102)77-43(37-90)31-42-26-24-23-25-27-42)84-54(96)46(28-29-50(74)94)79-56(98)48-32-44(92)35-88(48)65(107)72(19,20)87-63(105)69(13,14)81-55(97)47(30-38(2)3)78-51(95)34-75-58(100)52(39(4)5)80-61(103)68(11,12)85-64(106)71(17,18)86-62(104)70(15,16)83-59(101)53(40(6)7)76-41(8)91/h23-27,38-40,43-49,52-53,90,92-93H,22,28-37H2,1-21H3,(H2,74,94)(H,75,100)(H,76,91)(H,77,102)(H,78,95)(H,79,98)(H,80,103)(H,81,97)(H,82,99)(H,83,101)(H,84,96)(H,85,106)(H,86,104)(H,87,105) |
| InChI Key | YOMNVVBADFJOPW-UHFFFAOYSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 239°C |
Reference Reading
1. A natural, single-residue substitution yields a less active peptaibiotic: the structure of bergofungin A at atomic resolution
Renate Gessmann, Danny Axford, Hans Brückner, Albrecht Berg, Kyriacos Petratos Acta Crystallogr F Struct Biol Commun. 2017 Feb 1;73(Pt 2):95-100. doi: 10.1107/S2053230X17001236. Epub 2017 Jan 27.
Bergofungin is a peptide antibiotic that is produced by the ascomycetous fungus Emericellopsis donezkii HKI 0059 and belongs to peptaibol subfamily 2. The crystal structure of bergofungin A has been determined and refined to 0.84 Å resolution. This is the second crystal structure of a natural 15-residue peptaibol, after that of samarosporin I. The amino-terminal phenylalanine residue in samarosporin I is exchanged to a valine residue in bergofungin A. According to agar diffusion tests, this results in a nearly inactive antibiotic peptide compared with the moderately active samarosporin I. Crystals were obtained from methanol solutions of purified bergofungin mixed with water. Although there are differences in the intramolecular hydrogen-bonding scheme of samarosporin I, the overall folding is very similar for both peptaibols, namely 310-helical at the termini and α-helical in the middle of the molecules. Bergofungin A and samarosporin I molecules are arranged in a similar way in both lattices. However, the packing of bergofungin A exhibits a second solvent channel along the twofold axis. This latter channel occurs in the vicinity of the N-terminus, where the natural substitution resides.
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. 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.
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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 ╳
