Neomethymycin
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| Category | Antibiotics |
| Catalog number | BBF-01932 |
| CAS | 497-73-4 |
| Molecular Weight | 469.61 |
| Molecular Formula | C25H43NO7 |
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Description
Neomethymycin is a macrolide antibiotic produced by Str. venezuelae WC-3627 and WC-3629. It has activity against gram-positive bacteria and a few gram-negative bacteria.
Specification
| IUPAC Name | (3R,4S,5S,7R,9E,11R,12S)-4-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-12-[(1R)-1-hydroxyethyl]-3,5,7,11-tetramethyl-1-oxacyclododec-9-ene-2,8-dione |
| Canonical SMILES | CC1CC(C(=O)C=CC(C(OC(=O)C(C1OC2C(C(CC(O2)C)N(C)C)O)C)C(C)O)C)C |
| InChI | InChI=1S/C25H43NO7/c1-13-9-10-20(28)14(2)11-15(3)22(17(5)24(30)32-23(13)18(6)27)33-25-21(29)19(26(7)8)12-16(4)31-25/h9-10,13-19,21-23,25,27,29H,11-12H2,1-8H3/b10-9+/t13-,14-,15+,16-,17-,18-,19+,21-,22+,23+,25+/m1/s1 |
| InChI Key | UEIVQYHYALXCBD-OTUJEKPESA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 627.8±55.0°C at 760 mmHg |
| Density | 1.1±0.1 g/cm3 |
Reference Reading
1. Nickel-Catalyzed Regiodivergent Approach to Macrolide Motifs
Abdur-Rafay Shareef, David H Sherman, John Montgomery Chem Sci. 2012 Jan 1;3(3):892-895. doi: 10.1039/C2SC00866A. Epub 2011 Dec 6.
A strategy for regiochemical reversal of reductive macrocyclizations of aldehydes and terminal alkynes has been developed. Using an advanced synthetic intermediate directed towards the methymycin/neomethymycin class of macrolides, selective endocyclization provides the natural twelve-membered ring series, whereas ligand alteration enables selective exocyclization to provide access to the unnatural eleven-membered ring series. The twelve-membered ring adduct was converted to 10-deoxymethynolide, completing an efficient total synthesis of this natural product.
2. Biocatalytic synthesis of pikromycin, methymycin, neomethymycin, novamethymycin, and ketomethymycin
Douglas A Hansen, Christopher M Rath, Eli B Eisman, Alison R H Narayan, Jeffrey D Kittendorf, Jonathan D Mortison, Yeo Joon Yoon, David H Sherman J Am Chem Soc. 2013 Jul 31;135(30):11232-8. doi: 10.1021/ja404134f. Epub 2013 Jul 18.
A biocatalytic platform that employs the final two monomodular type I polyketide synthases of the pikromycin pathway in vitro followed by direct appendage of D-desosamine and final C-H oxidation(s) in vivo was developed and applied toward the synthesis of a suite of 12- and 14-membered ring macrolide natural products. This methodology delivered both compound classes in 13 steps (longest linear sequence) from commercially available (R)-Roche ester in >10% overall yields.
3. Characterization of glycosyltransferase DesVII and its auxiliary partner protein DesVIII in the methymycin/picromycin biosynthetic pathway
Svetlana A Borisova, Hung-Wen Liu Biochemistry. 2010 Sep 21;49(37):8071-84. doi: 10.1021/bi1007657.
The in vitro characterization of the catalytic activity of DesVII, the glycosyltransferase involved in the biosynthesis of the macrolide antibiotics methymycin, neomethymycin, narbomycin, and pikromycin in Streptomyces venezuelae, is described. DesVII is unique among glycosyltransferases in that it requires an additional protein component, DesVIII, for activity. Characterization of the metabolites produced by a S. venezuelae mutant lacking the desVIII gene confirmed that desVIII is important for the biosynthesis of glycosylated macrolides but can be replaced by at least one of the homologous genes from other pathways. The addition of recombinant DesVIII protein significantly improves the glycosylation efficiency of DesVII in the in vitro assay. When affinity-tagged DesVII and DesVIII proteins were coproduced in Escherichia coli, they formed a tight (αβ)(3) complex that is at least 10(3)-fold more active than DesVII alone. The formation of the DesVII/DesVIII complex requires coexpression of both genes in vivo and cannot be fully achieved by mixing the individual protein components in vitro. The ability of the DesVII/DesVIII system to catalyze the reverse reaction with the formation of TDP-desosamine was also demonstrated in a transglycosylation experiment. Taken together, our data suggest that DesVIII assists the folding of DesVII during protein production and remains tightly bound during catalysis. This requirement must be taken into consideration in the design of combinatorial biosynthetic experiments with new glycosylated macrolides.
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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 ╳
