Nodusmicin
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| Category | Antibiotics |
| Catalog number | BBF-04278 |
| CAS | 76265-48-0 |
| Molecular Weight | 422.51 |
| Molecular Formula | C23H34O7 |
| Purity | >99% by HPLC |
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Description
It is an antibiotic produced by the strain of Saccharopolyspora hirsuta and Nocardia argentinensis. It is a co-metabolite of nargenicin, bearing the core macrocyclic lactone but lacking the pyrrole ester. It has anti-gram-positive bacteria and anaerobic bacteria activity.
Specification
| Synonyms | Antibiotic U 59761; Nodusmicin 1; [3R-[1E,3R*,4S*(R*),7S*,8aS*,10aR*,11R*,12R*,13R*,14R*,14aS*,14bS*]]-3,4,8,8a,10a,11,12,13,14,14a-Decahydro-12,14-dihydroxy-4-(1-hydroxyethyl)-7-methoxy-1,3,13-trimethyl-11,14b-epoxy-14bH-naphth[2,1-e]oxecin-6(7H)-one; (1E,3R,4S,7S,8aS,10aR,11R,12R,13R,14R,14aS,14bS)-3,4,8,8a,10a,11,12,13,14,14a-decahydro-12,14-dihydroxy-4-[(1R)-1-hydroxyethyl]-7-methoxy-1,3,13-trimethyl-11,14b-epoxy-14bH-naphth[2,1-e]oxecin-6(7H)-one; U 59761 |
| Storage | Store at -20°C |
| IUPAC Name | (1S,3R,4R,5R,6R,7S,8R,11S,13S,16S,17R,18Z)-4,6-dihydroxy-16-[(1R)-1-hydroxyethyl]-13-methoxy-5,17,19-trimethyl-2,15-dioxatetracyclo[9.8.0.01,7.03,8]nonadeca-9,18-dien-14-one |
| Canonical SMILES | CC1C=C(C23C(CC(C(=O)OC1C(C)O)OC)C=CC4C2C(C(C(C4O3)O)C)O)C |
| InChI | InChI=1S/C23H34O7/c1-10-8-11(2)23-14(9-16(28-5)22(27)29-20(10)13(4)24)6-7-15-17(23)18(25)12(3)19(26)21(15)30-23/h6-8,10,12-21,24-26H,9H2,1-5H3/b11-8-/t10-,12-,13-,14-,15-,16+,17+,18-,19-,20+,21-,23+/m1/s1 |
| InChI Key | LUCYVUUQBYQHOV-GFCOOTNGSA-N |
| Source | Nocardia sp. |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Bacteria |
| Boiling Point | 629.3±55.0°C at 760 mmHg |
| Melting Point | 201-206°C |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Biosynthesis of the nargenicin A1 pyrrole moiety from Nocardia sp. CS682
Niraj Aryal, Janardan Lamichhane, Dinesh Koju, Saurabh Bhattarai, Sushila Maharjan, Jae Kyung Sohng Appl Microbiol Biotechnol . 2012 Jan;93(2):687-96. doi: 10.1007/s00253-011-3567-x.
A number of structurally diverse natural products harboring pyrrole moieties possess a wide range of biological activities. Studies on biosynthesis of pyrrole ring have shown that pyrrole moieties are derived from L-proline. Nargenicin A(1), a saturated alicyclic polyketide from Nocardia sp. CS682, is a pyrrole-2-carboxylate ester of nodusmicin. We cloned and identified a set of four genes from Nocardia sp. CS682 that show sequence similarity to the respective genes involved in the biosynthesis of the pyrrole moieties of pyoluteorin in Pseudomonas fluorescens, clorobiocin in Streptomyces roseochromogenes subsp. Oscitans, coumermycin A(1) in Streptomyces rishiriensis, one of the pyrrole rings of undecylprodigiosin in Streptomyces coelicolor, and leupyrrins in Sorangium cellulosum. These genes were designated as ngnN4, ngnN5, ngnN3, and ngnN2. In this study, we presented the evidences that the pyrrole moiety of nargenicin A(1) was also derived from L-proline by the coordinated action of three proteins, NgnN4 (proline adenyltransferase), NgnN5 (proline carrier protein), and NgnN3 (flavine-dependent acyl-coenzyme A dehydrogenases). Biosynthesis of pyrrole moiety in nargenicin A(1) is initiated by NgnN4 that catalyzes ATP-dependent activation of L-proline into L-prolyl-AMP, and the latter is transferred to NgnN5 to create prolyl-S-peptidyl carrier protein (PCP). Later, NgnN3 catalyzes the two-step oxidation of prolyl-S-PCP into pyrrole-2-carboxylate. Thus, this study presents another example of a pyrrole moiety biosynthetic pathway that uses a set of three genes to convert L-proline into pyrrole-2-carboxylic acid moiety.
2. Coloradocin, an antibiotic from a new Actinoplanes. II. Identity with luminamicin and elucidation of structure
D N Whittern, R R Rasmussen, J B McAlpine, M H Scherr, A M Buko J Antibiot (Tokyo) . 1987 Oct;40(10):1383-93. doi: 10.7164/antibiotics.40.1383.
Coloradocin was isolated from a fermentation broth by adsorption onto Amberlite XAD-2. The activity was eluted in MeOH and purified by gel filtration on Shephadex LH-20, followed by liquid-liquid chromatography on diol-bonded silica gel. The last two steps in the purification of this antibiotic included reverse-phase chromatography on C18-bonded silica gel and countercurrent chromatography on an Ito Coil Planet Centrifuge to give material of 90% purity. Analytically pure material was obtained by preparative HPLC. As a result of extensive homo and heteronuclear two-dimensional NMR studies, a structure was proposed for coloradocin. The structure consists of a decalin ring system fused to a 10-membered macrolactone which in turn is fused to a 14-membered macrolactone possessing an enol ether in conjugation with an unsaturated cyclic anhydride functionality. Coloradocin is related to a small class of antibiotics which include nodusmicin and nargenicin and was shown to be identical to luminamicin for which no structure has been reported.
3. Stereostructure of luminamicin, an anaerobic antibiotic, via molecular dynamics, NMR spectroscopy, and the modified Mosher method
Yusuke Sakoh, Toshiaki Sunazuka, Masaki Handa, Shuichi Hirono, Satoshi Omura, Hideaki Ui, Yuzuru Iwai, Hiroaki Gouda Proc Natl Acad Sci U S A . 2005 Dec 20;102(51):18286-91. doi: 10.1073/pnas.0508425102.
The absolute stereostructure of luminamicin, an anaerobic antibiotic, has been determined by using conformational analysis via high-temperature molecular dynamics, NMR spectroscopy, and the modified Mosher method. It was found that luminamicin has the S, S, R, R, R, R, S, S, S, R, and S configurations at C2, C4, C7, C9, C10, C11, C12, C13, C16, C28, and C29, respectively. This configuration is the same as that found in nodusmicin, which has a chemical structure quite similar to luminamicin. The structure of luminamicin consists of three different rings, i.e., a decalin ring, a 10-membered macrolactone ring, and a 14-membered macrolactone ring. The resulting three-dimensional structure of luminamicin shows an interesting feature in that the maleic anhydride functionality in conjugation with the enol ether group of the 14-membered macrolactone is nearly perpendicular to the plane of the other two rings.
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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 ╳
