Fragilomycin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-01441 |
| CAS | |
| Molecular Weight | 1175.22 |
| Molecular Formula | C54H82N2O26 |
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Description
Fragilomycin A is produced by the strain of Streptosporangium fragilis SK & F-BC2496. It has anti-gram-negative bacteria and anaerobic bacteria activity.
Properties
| Appearance | Orange-Red Solid |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Melting Point | 197-199°C |
Reference Reading
1. Cytochrome P450 oxidase SlgO1 catalyzes the biotransformation of tirandamycin C to a new tirandamycin derivative
Xuhua Mo, Chun Gui, Song Yang 3 Biotech. 2019 Mar;9(3):71. doi: 10.1007/s13205-019-1611-1. Epub 2019 Feb 9.
In the present study, an Escherichia coli whole cell system with overexpression of a cytochrome P450 oxidase SlgO1 involved in streptolydigin biosynthetic pathway, an E. coli flavodoxin NADP+ oxidoreductase (EcFLDR), and an E. coli flavodoxin A (EcFLDA) were constructed. Biotransformation experiments revealed that SlgO1 can convert tirandamycin C to tirandamycin F, indicating that it can introduce a hydroxyl group into the C-10 position of tirandamycin C. Subsequently, slgO1 was cloned into pSET152AKE vector under the downstream of ermE* promoter, which was, respectively, introduced into Streptomyces sp. SCSIO1666 (tirandamycin B producer), Streptomyces sp. Ju1008 (tirandamycin C producer), and Streptomyces sp. Ju1009 (tirandamycin E producer). A novel tirandamycin derivative tirandamycin L accumulated in the engineered strain Streptomyces sp. Ju1008::slgO1 was isolated and its structure was determined on the basis of nuclear magnetic resonance (NMR) and mass spectrometry. Unlike most of the identified tirandamycins, tirandamycin L possessed a rare C-11-C-12 saturated bond as well as a C-10 ketone moiety. In addition, tirandamycin L showed weaker antibacterial activity. Based on the structure of tirandamycin L, SlgO1 was proposed to be responsible for multiple modifications toward tirandamycin C, including the formation of C-10 hydroxyl and C-11-C-12 saturated bond.
2. Discovery of a new family of Dieckmann cyclases essential to tetramic acid and pyridone-based natural products biosynthesis
Chun Gui, Qinglian Li, Xuhua Mo, Xiangjing Qin, Junying Ma, Jianhua Ju Org Lett. 2015 Feb 6;17(3):628-31. doi: 10.1021/ol5036497. Epub 2015 Jan 26.
Bioinformatic analyses indicate that TrdC, SlgL, LipX2, KirHI, and FacHI belong to a group of highly homologous proteins involved in biosynthesis of actinomycete-derived tirandamycin B, streptolydigin, α-lipomycin, kirromycin, and factumycin, respectively. However, assignment of their biosynthetic roles has remained elusive. Gene inactivation and complementation, in vitro biochemical assays with synthetic analogues, point mutations, and phylogenetic tree analyses reveal that these proteins represent a new family of Dieckmann cyclases that drive tetramic acid and pyridone scaffold biosynthesis.
3. Unified synthesis of tirandamycins and streptolydigins
Hikaru Yoshimura, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama Chem Commun (Camb). 2015 Dec 11;51(95):17004-7. doi: 10.1039/c5cc07749d.
The asymmetric total syntheses of tirandamycins A-D and tirandalydigin as well as the synthesis of the left-hand fragment of streptolydiginone and streptolydigin from a common intermediate are described. The comprehensive approach features the highly enantio- and diastereoselective assembly of the anti,anti,syn-stereotetrad unit which relies on a cinchona alkaloid-catalyzed asymmetric Morita-Baylis-Hillman reaction.
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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 ╳
