Megalomicin B
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| Category | Antibiotics |
| Catalog number | BBF-02313 |
| CAS | 49669-75-2 |
| Molecular Weight | 919.15 |
| Molecular Formula | C46H82N2O16 |
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Description
It is produced by the strain of Micromonospora megalomice var. megalomicea NRRL 3274. It is a macrolide antibiotic. It has anti-bacterial and mycobacterium activity, the activity is the strongest under alkaline condition, serum can reduce the activity of 20%-30%. It has protective effect on mice infected with Staphylococcus aureus or pneumococcus.
Specification
| Synonyms | W-847-B; 4'-Acetylmegalomycin A; Antibiotic XK-41B1; Megalomycin A 4'-O-acetate; XK-41-B1 |
| IUPAC Name | [(2S,3S,4R,6R)-6-[[(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-7-[(2S,4R,5R,6S)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-3,5,7,9,11,13-hexamethyl-2,10-dioxo-oxacyclotetradec-4-yl]oxy]-4-hydroxy-2,4-dimethyloxan-3-yl] acetate |
| Canonical SMILES | CCC1C(C(C(C(=O)C(CC(C(C(C(C(C(=O)O1)C)OC2CC(C(C(O2)C)OC(=O)C)(C)O)C)OC3C(C(CC(O3)C)N(C)C)O)(C)OC4CC(C(C(O4)C)O)N(C)C)C)C)O)(C)O |
| InChI | InChI=1S/C46H82N2O16/c1-17-32-46(12,56)39(53)24(4)35(50)22(2)20-45(11,64-33-19-31(48(15)16)36(51)27(7)58-33)40(63-43-37(52)30(47(13)14)18-23(3)57-43)25(5)38(26(6)42(54)61-32)62-34-21-44(10,55)41(28(8)59-34)60-29(9)49/h22-28,30-34,36-41,43,51-53,55-56H,17-21H2,1-16H3/t22-,23-,24+,25+,26-,27+,28+,30+,31-,32-,33+,34+,36+,37-,38+,39-,40-,41+,43+,44-,45-,46-/m1/s1 |
| InChI Key | WJOASKOPJZDBAH-WKBCHECCSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Mycobacteria |
| Boiling Point | 927.8°C at 760 mmHg |
| Melting Point | 135-140°C (dec.) |
| Density | 1.22 g/cm3 |
| Solubility | Soluble in Chloroform, Ethanol |
Reference Reading
1. In vivo characterization of the dTDP-D-desosamine pathway of the megalomicin gene cluster from Micromonospora megalomicea
Eduardo Rodríguez, Salvador Peirú, John R Carney, Hugo Gramajo Microbiology (Reading). 2006 Mar;152(Pt 3):667-673. doi: 10.1099/mic.0.28680-0.
In vivo reconstitution of the dTDP-D-desosamine pathway of the megalomicin gene cluster from Micromonospora megalomicea was achieved by expression of the genes in Escherichia coli. LC/MS/MS analysis of the dTDP-sugar intermediates produced by operons containing different sets of genes showed that production of dTDP-D-desosamine from dtdp-4-keto-6-deoxy-D-glucose requires only four biosynthetic steps, catalysed by MegCIV, MegCV, MegDII and MegDIII, and that MegCII is not involved. Instead, bioconversion studies demonstrated that MegCII is needed together with MegCIII to catalyse transfer of D-desosamine to 3-alpha-mycarosylerythronolide B.
2. Characterization of the heterodimeric MegBIIa:MegBIIb aldo-keto reductase involved in the biosynthesis of L-mycarose from Micromonospora megalomicea
Salvador Peirú, Eduardo Rodríguez, Chau Q Tran, John R Carney, Hugo Gramajo Biochemistry. 2007 Jul 10;46(27):8100-9. doi: 10.1021/bi700396n. Epub 2007 Jun 16.
Two putative C3-ketoreductases, MegBIIa and MegBIIb (formerly MegBII and MegDVII, respectively), homologues to members of the family 12 of aldo-keto reductase (AKR12) superfamily of enzymes, were identified in the megalomicin gene cluster from Micromonospora megalomicea. Proteins from this family are involved in the metabolism of TDP-sugars by actinomycetes. MegBIIa was originally proposed to be involved in the l-mycarose biosynthetic pathway, while MegBIIb in the l-megosamine biosynthetic pathway. In this work we have investigated the role of these proteins in the biosynthesis of dTDP-l-mycarose. In vivo analysis of the dTDP-sugar intermediates indicated that neither MegBIIa nor its homologue, MegBIIb, was a fully active enzyme by itself. Surprisingly, C3-ketoreductase activity was observed only in the presence of both MegBIIa and MegBIIb, suggesting the formation of an active complex. Copurification and size exclusion chromatography experiments confirmed that MegBIIa and MegBIIb interact forming a 1:1 heterodimeric complex. Finally, a mycarose operon containing megBIIa and megBIIb together with the other biosynthetic genes of the l-mycarose pathway was constructed and tested by bioconversion experiments in Escherichia coli. High levels of mycarosyl-erythronolide B were produced under the condition tested, confirming the role of these two proteins in this metabolic pathway.
3. Physio-Biochemical Composition and Untargeted Metabolomics of Cumin (Cuminum cyminum L.) Make It Promising Functional Food and Help in Mitigating Salinity Stress
Sonika Pandey, Manish Kumar Patel, Avinash Mishra, Bhavanath Jha PLoS One. 2015 Dec 7;10(12):e0144469. doi: 10.1371/journal.pone.0144469. eCollection 2015.
Cumin is an annual, aromatic, herbaceous, medicinal, spice plant, most widely used as a food additive and flavoring agent in different cuisines. The study is intended to comprehensively analyse physiological parameters, biochemical composition and metabolites under salinity stress. Seed germination index, rate of seed emergence, rate of seed germination, mean germination time, plant biomass, total chlorophyll and carotenoid contents decreased concomitantly with salinity. In contrast, total antioxidant activity, H2O2, proline and MDA contents increased concurrently with stress treatments. Total phenolic and flavonoid contents were decreased initially about 1.4-fold at 50 mM, and thereafter increased about 1.2-fold at 100 mM NaCl stress. Relative water content remained unchanged up to 50 mM NaCl stress, and thereafter decreased significantly. About 2.8-fold electrolyte leakage was found in 50 mM, which increases further 4-fold at 100 mM NaCl stress. Saturated fatty acids (FAs) increased gradually with salinity, whereas unsaturation index and degree of unsaturation change arbitrarily along with the percent quantity of unsaturated FAs. Total lipid and fatty acid composition were significantly influenced by salinity stress. A total of 45 differentially expressed metabolites were identified, including luteolin, salvianolic acid, kaempferol and quercetin, which are phenolic, flavonoid or alkaloids in nature and contain antioxidant activities. Additionally, metabolites with bioactivity such as anticancerous (docetaxel) and antimicrobial (megalomicin) properties were also identified. The study evidenced that plant shoots are a rich source of metabolites, essential amino acids, phenolic compounds and fatty acids, which unveil the medicinal potential of this plant, and also provide useful insight about metabolic responses under salinity stress.
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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 ╳
