Sperabillin D

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Sperabillin D
Category Antibiotics
Catalog number BBF-02927
CAS 111465-40-8
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 and E. coli O-111 with ED50 (mg/kg, subcutaneous) of 1.82 and 55.9, respectively.

Specification

Synonyms D-xylo-Heptonamide, 3-amino-N-(3-amino-3-iminopropyl)-2,3,4,6,7-pentadeoxy-6-[[(2E,4E)-1-oxo-2,4-hexadien-1-yl]amino]-; D-xylo-Heptonamide, 3-amino-N-(3-amino-3-iminopropyl)-2,3,4,6,7-pentadeoxy-6-((1-oxo-2,4-hexadienyl)amino)-, (E,E)-; Antibiotic TAN 749D
IUPAC Name (3R,5R,6R)-3-amino-N-(3-amino-3-iminopropyl)-6-[[(2E,4E)-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-PXRNKZPESA-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. 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.
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. 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.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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