Phenelfamycin E
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| Category | Antibiotics |
| Catalog number | BBF-02676 |
| CAS | 114451-31-9 |
| Molecular Weight | 1226.44 |
| Molecular Formula | C65H95NO21 |
| Purity | >95% by HPLC |
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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. It is an antibiotic with good activity against gram-positive bacteria, notably clostridium difficile.
Specification
| Synonyms | Ganefromycin-α; Antibiotic LL-E 19020a; Ganefromycin a; LL-E 19020a; Benzeneacetic acid,(2R,3R,4R,6S)-2-[(1S)-2-[[(2E,4E,6S,7S)-7-[(2R,4S,5S)-5-[(1E,3E,5E)-6-carboxy-1,3,5-hexatrienyl]tetrahydro-4-hydroxy-2-furanyl]-6-methoxy-5-methyl-2,4-octadienyl]amino]-1-[[[O-2,6-dideoxy-3-O-methyl-a-L-lyxo-hexopyranosyl-(1,4)-O-2,6-dideoxy-3-O-methyl-b-L-ribo-hexopyranosyl-(1,4)-2,6-dideoxy-3-O-methyl-a-L-lyxo-hexopyranosyl]oxy]methyl]-2-oxoethyl]tetrahydro-2,4-dihydroxy-5,5-dimethyl-6-[(1E,3Z)-1,3-pentadienyl]-2H-pyran-3-yl ester |
| Storage | Store at -20°C |
| IUPAC Name | (2E,4E,6E)-7-[(2S,3S,5R)-5-[(2S,3S,4E,6E)-8-[[(2S)-2-[(2R,3R,4R,6S)-2,4-dihydroxy-5,5-dimethyl-6-[(1E,3Z)-penta-1,3-dienyl]-3-(2-phenylacetyl)oxyoxan-2-yl]-3-[(2R,4S,5R,6S)-5-[(2R,4R,5S,6S)-5-[(2S,4S,5R,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-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)OC3CC(C(C(O3)C)OC4CC(C(C(O4)C)O)OC)OC)OC)C(=O)NCC=CC=C(C)C(C(C)C5CC(C(O5)C=CC=CC=CC(=O)O)O)OC)O)OC(=O)CC6=CC=CC=C6)O)(C)C |
| InChI | InChI=1S/C65H95NO21/c1-13-14-18-29-51-64(7,8)61(72)62(84-53(70)32-43-26-19-17-20-27-43)65(74,87-51)44(63(73)66-31-24-23-25-38(2)58(78-12)39(3)47-33-45(67)46(83-47)28-21-15-16-22-30-52(68)69)37-79-54-35-49(76-10)59(41(5)81-54)86-56-36-50(77-11)60(42(6)82-56)85-55-34-48(75-9)57(71)40(4)80-55/h13-30,39-42,44-51,54-62,67,71-72,74H,31-37H2,1-12H3,(H,66,73)(H,68,69)/b14-13-,16-15+,24-23+,28-21+,29-18+,30-22+,38-25+/t39-,40-,41-,42-,44+,45-,46-,47+,48-,49-,50+,51-,54+,55-,56+,57+,58+,59+,60-,61-,62+,65+/m0/s1 |
| InChI Key | UDVVGDCMWCVRCO-WOPDTIQPSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Light Brown Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 1166.0°C at 760 mmHg |
| Melting Point | 138°C |
| Density | 1.26 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Process-scale reversed-phase high-performance liquid chromatography purification of LL-E19020 alpha, a growth promoting antibiotic produced by Streptomyces lydicus ssp. tanzanius
F Pinho, D R Williams, G T Carter, D B Borders J Chromatogr . 1989 Dec 22;484:381-90. doi: 10.1016/s0021-9673(01)88985-8.
LL-E19020 alpha is a novel antibiotic produced by fermentation of the soil microorganism Streptomyces lydicus ssp. tanzanius. The compound is highly effective in inducing increases in weight gain and feed conversion efficiency in livestock. In order to obtain kilogram quantities of the material for field trials, pilot plant scale fermentations (up to 7500 l) were carried out. The antibiotic was recovered from the fermentation broth by solvent extraction. The resultant crude extract was subjected to reversed-phase (C18) chromatography on a process-scale high-performance liquid chromatography (HPLC) unit. The heart of the instrumentation is the Millipore Kiloprep chromatograph with the standard 12-l cartridge column. The laboratory housing the chromatograph has been specifically designed for this work. Tanks for mobile phase preparation are mounted on load cells for precise measurement of components. In this explosion-proof laboratory, all solvent handling areas are well ventilated and a separate breathing air system is provided for the operators. For the purification of the LL-E19020 antibiotics, the mobile phase consisted of a gradient of acetonitrile in 0.1 M ammonium acetate at pH 4.5. The effluent was monitored by UV absorbance at 325 nm. Fractions were collected across the peaks of interest and these were analyzed by analytical HPLC. The maximum yield of LL-E19020 alpha obtained in a single run was approximately 100 g. The antibiotic was recovered from the mobile phase by extraction with methylene chloride. The methylene chloride phase was concentrated under reduced pressure to yield a gummy residue which was finally freeze-dried from tertiary butanol to yield an off-white solid suitable for blending with various feed components.
2. Relative and absolute configurations of ganefromycin alpha
T Andersson, K Nakanishi, G T Carter, N Berova Org Lett . 2000 Apr 6;2(7):919-22. doi: 10.1021/ol005598u.
The full structure of ganefromycin alpha has been determined. The relative configurations were determined from 3JH,H coupling constants and NOE data, while the absolute configurations in moleties A and B were determined separately by difference CD of their acylate derivatives, which showed typical exciton couplets. The configurations of the stereogenic centers in ganefromycin alpha are 8S, 9S, 11R, 12S, 13S, 21S, 22R, 23R, 24R, and 26S.
3. LL-E19020 alpha and beta, animal growth promoting antibiotics: taxonomy, fermentation and biological activity
N Kuck, J Goodman, W M Maiese, J Korshalla, M Greenstein, M J Wildey, S D Conner, H A Lechevalier, M P Lechevalier J Antibiot (Tokyo) . 1989 Oct;42(10):1489-93. doi: 10.7164/antibiotics.42.1489.
Antibacterial antibiotics LL-E19020 alpha and beta were isolated from the fermentation broth of an actinomycete strain. Based on cultural and physiological characteristics, culture LL-E19020 was identified as a new subspecies of Streptomyces lydicus. The LL-E19020 alpha and beta antibiotics were found to possess a very narrow antibacterial spectrum against human pathogens. In studies in chickens, LL-E19020 alpha demonstrated excellent growth promoting activity.
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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 ╳
