Methymycin
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| Category | Antibiotics |
| Catalog number | BBF-01931 |
| CAS | 497-72-3 |
| Molecular Weight | 469.61 |
| Molecular Formula | C25H43NO7 |
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Description
Methymycin 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,11S,12R)-4-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-12-ethyl-11-hydroxy-3,5,7,11-tetramethyl-1-oxacyclododec-9-ene-2,8-dione |
| Canonical SMILES | CCC1C(C=CC(=O)C(CC(C(C(C(=O)O1)C)OC2C(C(CC(O2)C)N(C)C)O)C)C)(C)O |
| InChI | InChI=1S/C25H43NO7/c1-9-20-25(6,30)11-10-19(27)14(2)12-15(3)22(17(5)23(29)32-20)33-24-21(28)18(26(7)8)13-16(4)31-24/h10-11,14-18,20-22,24,28,30H,9,12-13H2,1-8H3/b11-10+/t14-,15+,16-,17-,18+,20-,21-,22+,24+,25+/m1/s1 |
| InChI Key | HUKYPYXOBINMND-HYUJHOPRSA-N |
Properties
| Appearance | White Crystals |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 631.9±55.0°C at 760 mmHg |
| Density | 1.1±0.1 g/cm3 |
Reference Reading
1. Co-produced natural ketolides methymycin and pikromycin inhibit bacterial growth by preventing synthesis of a limited number of proteins
Mashal M Almutairi, Maxim S Svetlov, Douglas A Hansen, Nelli F Khabibullina, Dorota Klepacki, Han-Young Kang, David H Sherman, Nora Vázquez-Laslop, Yury S Polikanov, Alexander S Mankin Nucleic Acids Res. 2017 Sep 19;45(16):9573-9582. doi: 10.1093/nar/gkx673.
Antibiotics methymycin (MTM) and pikromycin (PKM), co-produced by Streptomyces venezuelae, represent minimalist macrolide protein synthesis inhibitors. Unlike other macrolides, which carry several side chains, a single desosamine sugar is attached to the macrolactone ring of MTM and PKM. In addition, the macrolactone scaffold of MTM is smaller than in other macrolides. The unusual structure of MTM and PKM and their simultaneous secretion by S. venezuelae bring about the possibility that two compounds would bind to distinct ribosomal sites. However, by combining genetic, biochemical and crystallographic studies, we demonstrate that MTM and PKM inhibit translation by binding to overlapping sites in the ribosomal exit tunnel. Strikingly, while MTM and PKM readily arrest the growth of bacteria, ~40% of cellular proteins continue to be synthesized even at saturating concentrations of the drugs. Gel electrophoretic analysis shows that compared to other ribosomal antibiotics, MTM and PKM prevent synthesis of a smaller number of cellular polypeptides illustrating a unique mode of action of these antibiotics.
2. A novel methymycin analog, 12-ketomethymycin N-oxide, produced by the heterologous expression of the large pikromycin/methymycin biosynthetic gene cluster of Streptomyces sp. AM4900
Reiko Ueoka, Junko Hashimoto, Ikuko Kozone, Takuya Hashimoto, Kei Kudo, Noritaka Kagaya, Hikaru Suenaga, Haruo Ikeda, Kazuo Shin-Ya Biosci Biotechnol Biochem. 2021 Mar 24;85(4):890-894. doi: 10.1093/bbb/zbaa111.
A novel methymycin analog, 12-ketomethymycin N-oxide, was produced by the heterologous expression of the pikromycin/methymycin biosynthetic gene cluster of Streptomyces sp. AM4900 together with 12-ketomethymycin, which was only isolated by the biotransformation of the synthetic intermediate before. Their structures were determined by the spectroscopic data and the chemical derivatization. 12-Ketomethymycin showed a weak cytotoxicity against SKOV-3 and Jurkat cells, although its N-oxide analog did not show any activity. Both showed no antibacterial activities against Escherichia coli and Micrococcus luteus.
3. Chemoenzymatic synthesis of fluorinated polyketides
Alexander Rittner, Mirko Joppe, Jennifer J Schmidt, Lara Maria Mayer, Simon Reiners, Elia Heid, Dietmar Herzberg, David H Sherman, Martin Grininger Nat Chem. 2022 Sep;14(9):1000-1006. doi: 10.1038/s41557-022-00996-z. Epub 2022 Jul 25.
Modification of polyketides with fluorine offers a promising approach to develop new pharmaceuticals. While synthetic chemical methods for site-selective incorporation of fluorine in complex molecules have improved in recent years, approaches for the biosynthetic incorporation of fluorine in natural compounds are still rare. Here, we report a strategy to introduce fluorine into complex polyketides during biosynthesis. We exchanged the native acyltransferase domain of a polyketide synthase, which acts as the gatekeeper for the selection of extender units, with an evolutionarily related but substrate tolerant domain from metazoan type I fatty acid synthase. The resulting polyketide-synthase/fatty-acid-synthase hybrid can utilize fluoromalonyl coenzyme A and fluoromethylmalonyl coenzyme A for polyketide chain extension, introducing fluorine or fluoro-methyl units in polyketide scaffolds. We demonstrate the feasibility of our approach in the chemoenzymatic synthesis of fluorinated 12- and 14-membered macrolactones and fluorinated derivatives of the macrolide antibiotics YC-17 and methymycin.
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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 ╳
