Dynemicin P

Dynemicin P

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Dynemicin P
Category Antibiotics
Catalog number BBF-01193
CAS 138370-13-5
Molecular Weight 515.47
Molecular Formula C28H21NO9

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Description

It is produced by the strain of Micromonospora chersina M956-1. Although the activity of this antibiotic is lower than Dynemicin A, it still has strong anti-gram-positive bacterial activity, such as Staphylococcus aureus FDA 209P (MIC is 0.08 μg/mL).

Specification

Synonyms (1R)-3,4,4a,13,14,14a-Hexahydro-3β,4a,6,8,11,14a-hexahydroxy-1β-methyl-4,14-[1,2]benzenonaphtho[2,3-c]phenanthridine-2,7,12(1H)-trione; 9,8,14-(1)Butanyl(4)ylideneanthra(1,2-b)benz(f)azocine-5,16,19-trione,8,9,14,15-tetrahydro-1,4,6,8,17,20-hexahydroxy-18-methyl-, (8R-(8alpha,9beta,14beta,17S*,18R*))-
IUPAC Name (2R,3S,4R,6R,7R,14S)-2,3,6,20,23,27-hexahydroxy-4-methyl-15-azaheptacyclo[14.12.0.02,7.03,14.08,13.017,26.019,24]octacosa-1(28),8,10,12,16,19,21,23,26-nonaene-5,18,25-trione
Canonical SMILES CC1C(=O)C(C2C3=CC=CC=C3C4C1(C2(C5=CC(=C6C(=C5N4)C(=O)C7=C(C=CC(=C7C6=O)O)O)O)O)O)O
InChI InChI=1S/C28H21NO9/c1-9-22(33)25(36)20-10-4-2-3-5-11(10)26-27(9,37)28(20,38)12-8-15(32)18-19(21(12)29-26)24(35)17-14(31)7-6-13(30)16(17)23(18)34/h2-9,20,25-26,29-32,36-38H,1H3/t9-,20+,25+,26-,27-,28-/m0/s1
InChI Key SMIPWYWDEUZLFV-BBURVQHASA-N

Properties

Appearance Blue Powder
Antibiotic Activity Spectrum gram-posotive becteria
Boiling Point 867.7 °C at 760 mmHg
Density 1.762 g/cm3
Solubility Soluble in Methanol, DMSO, Benzene

Reference Reading

1. Dynemicins O, P and Q: novel antibiotics related to dynemicin A isolation, characterization and biological activity
M Miyoshi-Saitoh, N Morisaki, Y Tokiwa, S Iwasaki, M Konishi, K Saitoh, T Oki J Antibiot (Tokyo). 1991 Oct;44(10):1037-44. doi: 10.7164/antibiotics.44.1037.
New antibiotics, dynemicins O (3), P (4) and Q (5), were isolated from the culture broth of Micromonospora chersina M956-1, the dynemicin A (1)-producing strain. An ethyl acetate extract of a tank culture was roughly separated by a column of Diaion SP-800 and was further purified by combining a variety of column chromatographies to afford a few mg of compounds 3, 4 and 5. Their structures, analyzed from the spectral data, had a bridging phenylene group, a vic-diol and an oxo group in place of the respective 1,5-diyn-3-ene bridge, the epoxide ring and the carboxyl group in dynemicin A. Their biological activities were evaluated against bacteria and tumor cells.

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