Sperabillin B
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| Category | Antibiotics |
| Catalog number | BBF-02925 |
| CAS | 111337-85-0 |
| Molecular Weight | 339.43 |
| Molecular Formula | C16H29N5O3 |
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Description
It is produced by the strain of Pseudomonas fluorescens YK-437. In vitro it has the effect of anti-pyomonas aeruginosa, alkali-producing faecal bacteria, acinetobacter calcium acetate and staphylococcus aureus. It also has antibacterial effect on Staphylococcus aureus and Pseudomonas aeruginosa resistant to methicillin, streptomycin, kanamycin, gentamicin, erythromycin, lincomycin, etc. It is used in mice infected with Staphylococcus aureus, Streptococcus pyogenes and E. coli O-111 with ED50 (mg/kg, subcutaneous) of 0.35, 8.84 and 27.3, respectively.
Specification
| Synonyms | D-xylo-Heptonamide, 3-amino-N-(3-amino-3-iminopropyl)-2,3,4,6,7-pentadeoxy-6-((1-oxo-2,4-hexadienyl)amino)-, (E,Z)-; D-xylo-Heptonamide, 3-amino-N-(3-amino-3-iminopropyl)-2,3,4,6,7-pentadeoxy-6-[[(2E,4Z)-1-oxo-2,4-hexadienyl]amino]-; Antibiotic TAN 749B |
| IUPAC Name | (3R,5R,6R)-3-amino-N-(3-amino-3-iminopropyl)-6-[[(2E,4Z)-hexa-2,4-dienoyl]amino]-5-hydroxyheptanamide |
| Canonical SMILES | CC=CC=CC(=O)NC(C)C(CC(CC(=O)NCCC(=N)N)N)O |
| InChI | InChI=1S/C16H29N5O3/c1-3-4-5-6-15(23)21-11(2)13(22)9-12(17)10-16(24)20-8-7-14(18)19/h3-6,11-13,22H,7-10,17H2,1-2H3,(H3,18,19)(H,20,24)(H,21,23)/b4-3-,6-5+/t11-,12-,13-/m1/s1 |
| InChI Key | HGBIYXQMCATWPJ-HPLJFFTKSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Density | 1.21 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1. Sperabillins, new antibacterial antibiotics with potent in vivo activity. Taxonomy, fermentation, isolation and biological activity
N Katayama, Y Nozaki, S Tsubotani, M Kondo, S Harada, H Ono J Antibiot (Tokyo). 1992 Jan;45(1):10-9. doi: 10.7164/antibiotics.45.10.
A Gram-negative bacterium was found to produce new antibacterial antibiotics, sperabillins A, B, C and D, and the producing bacterium was characterized and identified as Pseudomonas fluorescens YK-437. Sperabillins were isolated by column chromatographies using cation-exchange resins, activated carbon and cation-exchange Sephadex, and preparative reverse-phase HPLC. Sperabillins showed antibacterial activity against Gram-negative and Gram-positive bacteria including antibiotic-resistant strains of Pseudomonas aeruginosa and Staphylococcus aureus. Sperabillin A inhibited DNA, RNA, protein, and cell wall biosynthesis in Escherichia coli. Sperabillins showed good protective effects in experimentally infected mice.
2. Asymmetric total synthesis of sperabillins B and D via lithium amide conjugate addition
Stephen G Davies, Jane R Haggitt, Osamu Ichihara, Richard J Kelly, Michael A Leech, Anne J Price Mortimer, Paul M Roberts, Andrew D Smith Org Biomol Chem. 2004 Sep 21;2(18):2630-49. doi: 10.1039/B404962D. Epub 2004 Aug 24.
Diastereoselective conjugate addition of homochiral lithium (R)-N-allyl-N-alpha-methylbenzylamide to methyl (2E,5E)-hepatadienoate, followed by protecting group manipulation and subsequent iodocyclocarbamation allows a concise route to the core fragment, methyl (3R,5R,6R)-3,6-diamino-5-hydroxyheptanoate, of sperabillins B and D. Differentiation between the C-3 and C-6 primary amino groups of this core amino acid was readily achieved by treatment with acetone, giving the 5,6-isopropylidene and C-3-imine protected diamine, with subsequent regioselective acylation of the C-6-nitrogen facilitating the total synthesis of sperabillin D in 10.8% overall yield, and the first asymmetric synthesis of sperabillin B in 5.8% overall yield.
3. Synthesis and antimicrobial activity of sperabillin derivatives
T Hida, S Tsubotani, N Katayama, Y Funabashi, H Natsugari, S Harada J Antibiot (Tokyo). 1993 May;46(5):803-12. doi: 10.7164/antibiotics.46.803.
Modification of sperabillins was carried out. The 2-amidinoethylamino moiety was removed by brief acidic hydrolysis. The 2,4-hexadienoyl moiety was hydrogenated to the hexanoyl moiety and this was cleaved by an enzymatic reaction using the cells of Pseudomonas acidovorans IFO 13582. The 2-amidinoethylamino and the 2,4-hexadienoyl moieties were replaced with other groups. The derivative which was prepared by condensation of two molar amounts of dehexadienoylsperabillin A with (E,E)-muconic acid showed better protective effects than sperabillin A against Gram-negative bacteria.
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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 ╳
