Phenelfamycin B
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| Category | Antibiotics |
| Catalog number | BBF-02393 |
| CAS | 118498-92-3 |
| Molecular Weight | 938.11 |
| Molecular Formula | C51H71NO15 |
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Description
It is produced by the strain of Str. violaceoniger AB 9991-80, Str. violaceoniger AB 1047T-33. It has effect against anaerobic bacteria.
Specification
| IUPAC Name | (2E,4E,6E)-7-[(2S,3S,5R)-5-[(2S,3S,4E,6E)-8-[[(2S)-2-[(2R,3R,4R,6S)-2,3-dihydroxy-5,5-dimethyl-6-[(1E,3Z)-penta-1,3-dienyl]-4-(2-phenylacetyl)oxyoxan-2-yl]-3-[(2R,4S,5R,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxypropanoyl]amino]-3-methoxy-4-methylocta-4,6-dien-2-yl]-3-hydroxyoxolan-2-yl]hepta-2,4,6-trienoic acid |
| Canonical SMILES | CC=CC=CC1C(C(C(C(O1)(C(COC2CC(C(C(O2)C)O)OC)C(=O)NCC=CC=C(C)C(C(C)C3CC(C(O3)C=CC=CC=CC(=O)O)O)OC)O)O)OC(=O)CC4=CC=CC=C4)(C)C |
| InChI | InChI=1S/C51H71NO15/c1-9-10-14-25-41-50(5,6)48(66-43(56)28-35-22-15-13-16-23-35)47(58)51(60,67-41)36(31-63-44-30-40(61-7)45(57)34(4)64-44)49(59)52-27-20-19-21-32(2)46(62-8)33(3)39-29-37(53)38(65-39)24-17-11-12-18-26-42(54)55/h9-26,33-34,36-41,44-48,53,57-58,60H,27-31H2,1-8H3,(H,52,59)(H,54,55)/b10-9-,12-11+,20-19+,24-17+,25-14+,26-18+,32-21+/t33-,34-,36+,37-,38-,39+,40-,41-,44+,45+,46+,47+,48-,51+/m0/s1 |
| InChI Key | VLBWFLKRBCOSGD-NMMXFFNGSA-N |
Properties
| Appearance | Light Brown Powder |
| Boiling Point | 1017.7±65.0°C (Predicted) |
| Melting Point | 118°C |
| Density | 1.25±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol |
Reference Reading
1. Resistance-Guided Discovery of Elfamycin Antibiotic Producers with Antigonococcal Activity
Venkateswarlu Yarlagadda, Ricardo Medina, Timothy A Johnson, Kalinka P Koteva, Georgina Cox, Maulik N Thaker, Gerard D Wright ACS Infect Dis. 2020 Dec 11;6(12):3163-3173. doi: 10.1021/acsinfecdis.0c00467. Epub 2020 Nov 7.
The rise of bacterial antibiotic resistance coupled with a diminished antibiotic drug pipeline underlines the importance of developing rational strategies to discover new antimicrobials. Microbially derived natural products are the basis for most of the antibiotic arsenal available to modern medicine. Here, we demonstrate a resistance-based approach to identify producers of elfamycins, an under-explored class of natural product antibiotics that target the essential translation factor EF-Tu. Antibiotic producers carry self-resistance genes to avoid suicide. These genes are often found within the same biosynthetic gene cluster (BGC) responsible for making the antibiotic, and we exploited this trait to identify members of the kirromycin class of elfamycin producers. Genome mining of Streptomyces spp. led to the identification of three isolates that harbor kirromycin-resistant EF-Tu (EF-TuKirR) within predicted natural product BGCs. Activity-guided purification on extracts of one of the Streptomyces isolates, which was not known to produce an elfamycin, identified it as a producer of phenelfamycin B, a linear polyketide. Phenelfamycin B demonstrates impressive antibacterial activity (MIC ~ 1 μg/mL) against multidrug-resistant Neisseria gonorrhoeae, a clinically important Gram negative pathogen. The antigonococcal activity of phenelfamycin was shown to be the result of inhibition of protein biosynthesis by binding to EF-Tu. These results indicate that a resistance-based approach of identifying elfamycin producers is translatable to other antibiotic classes that can identify new and overlooked antibiotics necessary to address the antibiotic crisis.
2. Phenelfamycins, a novel complex of elfamycin-type antibiotics. III. Activity in vitro and in a hamster colitis model
R N Swanson, D J Hardy, N L Shipkowitz, C W Hanson, N R Ramer, L J Coen, P B Fernandes J Antibiot (Tokyo). 1989 Jan;42(1):94-101. doi: 10.7164/antibiotics.42.94.
Phenelfamycins A, B, C, E, F and unphenelfamycin make up a recently isolated group of elfamycin-type antibiotics. All of the phenelfamycins were active against Gram-positive anaerobes, including Clostridium difficile. Phenelfamycin A was also active in vitro against Neisseria gonorrhoeae and Streptococci. Phenelfamycin A was found to be effective in prolonging the survival of hamsters in an animal model of C. difficile enterocolitis. After oral administration of phenelfamycin A to hamsters, antibiotic was detected in the caecal contents but not in the blood.
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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 ╳
