Narbomycin
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| Category | Antibiotics |
| Catalog number | BBF-02104 |
| CAS | 6036-25-5 |
| Molecular Weight | 509.68 |
| Molecular Formula | C28H47NO7 |
| Purity | >98% |
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Description
Narbomycin is produced by the strain of Str. narbonensis ETH 7346. It has anti-gram-positive bacterial activity and is cross-resistance with amycin. And it has no protective effect on mice infected with Streptococcus pyogenes.
Specification
| Synonyms | 12-Deoxypicromycin; SureCN691770; (3R,5R,6S,7S,9R,11E,13R,14R)-14-ethyl-3,5,7,9,13-pentamethyl-2,4,10-trioxooxacyclotetradec-11-en-6-yl 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranoside |
| Storage | Store at 2-8°C |
| IUPAC Name | (3R,5R,6S,7S,9R,11E,13R,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-3,5,7,9,13-pentamethyl-1-oxacyclotetradec-11-ene-2,4,10-trione |
| Canonical SMILES | CCC1C(C=CC(=O)C(CC(C(C(C(=O)C(C(=O)O1)C)C)OC2C(C(CC(O2)C)N(C)C)O)C)C)C |
| InChI | InChI=1S/C28H47NO7/c1-10-23-15(2)11-12-22(30)16(3)13-17(4)26(19(6)24(31)20(7)27(33)35-23)36-28-25(32)21(29(8)9)14-18(5)34-28/h11-12,15-21,23,25-26,28,32H,10,13-14H2,1-9H3/b12-11+/t15-,16-,17+,18-,19+,20-,21+,23-,25-,26+,28+/m1/s1 |
| InChI Key | OXFYAOOMMKGGAI-JLTOUBQASA-N |
Properties
| Appearance | Colorless Crystalline |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 656.8°C at 760 mmHg |
| Melting Point | 113.5-115°C |
| Density | 1.1 g/cm3 |
| Solubility | Soluble in Water, DMSO |
Reference Reading
1. Total synthesis of pikromycin
Hong-Se Oh, Han-Young Kang J Org Chem. 2012 Jan 20;77(2):1125-30. doi: 10.1021/jo201158q. Epub 2011 Dec 30.
The total synthesis of pikromycin (6), the first isolated macrolide antibiotic, was achieved. The target macrolide was retrosynthetically divided into two parts, pikronolide (6a) (aglycon) and D-desosamine. The aglycon was synthesized using key reactions such as an asymmetric aldol reaction, Yamaguchi esterification, and ring-closing metathesis. The aglycon was coupled successfully with the trichloroacetimidate derivative of D-desosamine under Lewis acidic conditions to afford pikromycin. Narbomycin (5) was also synthesized from narbonolide (5a) under identical conditions.
2. Engineered biosynthesis of glycosylated derivatives of narbomycin and evaluation of their antibacterial activities
Ah Reum Han, Pramod B Shinde, Je Won Park, Jaeyong Cho, So Ra Lee, Yeon Hee Ban, Young Ji Yoo, Eun Ji Kim, Eunji Kim, Sung Ryeol Park, Byung-Gee Kim, Dong Gun Lee, Yeo Joon Yoon Appl Microbiol Biotechnol. 2012 Feb;93(3):1147-56. doi: 10.1007/s00253-011-3592-9. Epub 2011 Sep 30.
A 14-membered macrolide antibiotic narbomycin produced from Streptomyces venezuelae ATCC 15439 is composed of polyketide macrolactone ring and D-desosamine as a deoxysugar moiety, which acts as an important determinant of its antibacterial activity. In order to generate diverse glycosylated derivatives of narbomycin, expression plasmids carrying different deoxysugar biosynthetic gene cassettes and the gene encoding a substrate-flexible glycosyltransferase DesVII were constructed and introduced into S. venezuelae YJ003 mutant strain bearing a deletion of thymidine-5'-diphospho-D-desosamine biosynthetic gene cluster. The resulting recombinants of S. venezuelae produced a range of new analogs of narbomycin, which possess unnatural sugar moieties instead of native deoxysugar D-desosamine. The structures of narbomycin derivatives were determined through nuclear magnetic resonance spectroscopy and mass spectrometry analyses and their antibacterial activities were evaluated in vitro against erythromycin-susceptible and -resistant Enterococcus faecium and Staphylococcus aureus. Substitution with L-rhamnose or 3-O-demethyl-D-chalcose was demonstrated to exhibit greater antibacterial activity than narbomycin and the clinically relevant erythromycin. This work provides new insight into the functions of deoxysugar biosynthetic enzymes and structure-activity relationships of the sugar moieties attached to the macrolides and demonstrate the potential of combinatorial biosynthesis for the generation of new macrolides carrying diverse sugars with increased antibacterial activities.
3. Analysis of transient and catalytic desosamine-binding pockets in cytochrome P-450 PikC from Streptomyces venezuelae
Shengying Li, Hugues Ouellet, David H Sherman, Larissa M Podust J Biol Chem. 2009 Feb 27;284(9):5723-30. doi: 10.1074/jbc.M807592200. Epub 2009 Jan 4.
The cytochrome P-450 PikC from Streptomyces venezuelae exhibits significant substrate tolerance and performs multiple hydroxylation reactions on structurally variant macrolides bearing the deoxyamino sugar desosamine. In previously determined co-crystal structures (Sherman, D. H., Li, S., Yermalitskaya, L. V., Kim, Y., Smith, J. A., Waterman, M. R., and Podust, L. M. (2006) J. Biol. Chem. 281, 26289-26297), the desosamine moiety of the native substrates YC-17 and narbomycin is bound in two distinct buried and surface-exposed binding pockets, mediated by specific interactions between the protonated dimethylamino group and the acidic amino acid residues Asp(50), Glu(85), and Glu(94). Although the Glu(85) and Glu(94) negative charges are essential for maximal catalytic activity of native enzyme, elimination of the surface-exposed negative charge at Asp(50) results in significantly enhanced catalytic activity. Nevertheless, the D50N substitution could not rescue catalytic activity of PikC(E94Q) based on lack of activity in the corresponding double mutant PikC(D50N/E94Q). To address the specific role for each desosamine-binding pocket, we analyzed the x-ray structures of the PikC(D50N) mutant co-crystallized with narbomycin (1.85A resolution) and YC-17 (3.2A resolution). In PikC(D50N), the desosamine moiety of both YC-17 and narbomycin was bound in a catalytically productive "buried site." This finding suggested a two-step substrate binding mechanism, whereby desosamine is recognized in the two subsites to allow the macrolide substrate to sequentially progress toward a catalytically favorable orientation. Collectively, the binding, mutagenesis, kinetic, and x-ray structural data suggest that enhancement of the catalytic activity of PikC(D50N) is due to the facilitated relocation of substrate to the buried site, which has higher binding affinity, as opposed to dissociation in solution from the transient "surface-exposed site."
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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 ╳
