Jawsamycin
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| Category | Antibiotics |
| Catalog number | BBF-03568 |
| CAS | 120500-69-8 |
| Molecular Weight | 565.70 |
| Molecular Formula | C32H43N3O6 |
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Description
It is produced by the strain of Streptoverticillium fervens. Jawsamycin had strong anti-filamentous fungal activity, and the MIC of Aspergillus Niger, Aureobasidium and Mucor was 0.05 μg/mL.
Specification
| Synonyms | FR-900848; FR900848 |
| IUPAC Name | (2E,4E)-N-[[(2R,3S,4R,5R)-5-(2,4-dioxo-1,3-diazinan-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-5-[(1S,2R)-2-[(1R,2R)-2-[(1R,2R)-2-[(1R,2S)-2-[(E)-2-[(1R,2R)-2-methylcyclopropyl]ethenyl]cyclopropyl]cyclopropyl]cyclopropyl]cyclopropyl]penta-2,4-dienamide |
| Canonical SMILES | CC1CC1C=CC2CC2C3CC3C4CC4C5CC5C=CC=CC(=O)NCC6C(C(C(O6)N7CCC(=O)NC7=O)O)O |
| InChI | InChI=1S/C32H43N3O6/c1-16-10-17(16)6-7-19-12-21(19)23-14-25(23)24-13-22(24)20-11-18(20)4-2-3-5-27(36)33-15-26-29(38)30(39)31(41-26)35-9-8-28(37)34-32(35)40/h2-7,16-26,29-31,38-39H,8-15H2,1H3,(H,33,36)(H,34,37,40)/b4-2+,5-3+,7-6+/t16-,17-,18-,19-,20-,21-,22+,23+,24-,25-,26-,29-,30-,31-/m1/s1 |
| InChI Key | QOOORVUXEUQEKV-KNLYTHMISA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 198-201°C |
| Density | 1.466 g/cm3 |
Reference Reading
1. Making and breaking carbon-carbon bonds in class C radical SAM methyltransferases
Marley A Brimberry, Liju Mathew, William Lanzilotta J Inorg Biochem. 2022 Jan;226:111636. doi: 10.1016/j.jinorgbio.2021.111636. Epub 2021 Oct 22.
Radical S-adenosylmethionine (SAM) enzymes utilize a [4Fe-4S]1+ cluster and S-(5'-adenosyl)-L-methionine, (SAM), to generate a highly reactive radical and catalyze what is arguably the most diverse set of chemical reactions for any known enzyme family. At the heart of radical SAM catalysis is a highly reactive 5'-deoxyadenosyl radical intermediate (5'-dAdo●) generated through reductive cleavage of SAM or nucleophilic attack of the unique iron of the [4Fe-4S]+ cluster on the 5' C atom of SAM. Spectroscopic studies reveal the 5'-dAdo● is transiently captured in an FeC bond (Ω species). In the presence of substrate, homolytic scission of this metal‑carbon bond regenerates the 5'-dAdo● for catalytic hydrogen atom abstraction. While reminiscent of the adenosylcobalamin mechanism, radical SAM enzymes appear to encompass greater catalytic diversity. In this review we discuss recent developments for radical SAM enzymes involved in unique chemical rearrangements, specifically regarding class C radical SAM methyltransferases. Illuminating this class of radical SAM enzymes is especially significant as many enzymes have been shown to play critical roles in pathogenesis and the synthesis of novel antimicrobial compounds.
2. Novel Promising Antifungal Target Proteins for Conquering Invasive Fungal Infections
Cheng Zhen, Hui Lu, Yuanying Jiang Front Microbiol. 2022 Jun 16;13:911322. doi: 10.3389/fmicb.2022.911322. eCollection 2022.
Invasive fungal infections (IFIs) pose a serious clinical problem, but the antifungal arsenal is limited and has many disadvantages, such as drug resistance and toxicity. Hence, there is an urgent need to develop antifungal compounds that target novel target proteins of pathogenic fungi for treating IFIs. This review provides a comprehensive summary of the biological functions of novel promising target proteins for treating IFIs in pathogenic fungi and their inhibitors. Inhibitors of inositol phosphoramide (IPC) synthases (such as Aureobasidin A, Khafrefungin, Galbonolide A, and Pleofungin A) have potent antifungal activities by inhibiting sphingolipid synthesis. Disrupting glycosylphosphatidylinositol (GPI) biosynthesis by Jawsamycin (an inhibitor of Spt14), M720 (an inhibitor of Mcd4), and APX001A (an inhibitor of Gwt1) is a promising strategy for treating IFIs. Turbinmicin is a natural-compound inhibitor of Sec14 and has extraordinary antifungal efficacy, broad-antifungal spectrum, low toxicity, and is a promising new compound for treating IFIs. CMLD013075 targets fungal heat shock protein 90 (Hsp90) and has remarkable antifungal efficacy. Olorofim, as an inhibitor of dihydrolactate dehydrogenase, is a breakthrough drug treatment for IFIs. These novel target proteins and their inhibitors may overcome the limitations of currently available antifungal drugs and improve patient outcomes in the treatment of IFIs.
3. Electrochemical borylation of carboxylic acids
Lisa M Barton, Longrui Chen, Donna G Blackmond, Phil S Baran Proc Natl Acad Sci U S A. 2021 Aug 24;118(34):e2109408118. doi: 10.1073/pnas.2109408118.
A simple electrochemically mediated method for the conversion of alkyl carboxylic acids to their borylated congeners is presented. This protocol features an undivided cell setup with inexpensive carbon-based electrodes and exhibits a broad substrate scope and scalability in both flow and batch reactors. The use of this method in challenging contexts is exemplified with a modular formal synthesis of jawsamycin, a natural product harboring five cyclopropane 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 ╳
