Rugulotrosin A
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| Category | Antibiotics |
| Catalog number | BBF-04287 |
| CAS | 685135-81-3 |
| Molecular Weight | 638.57 |
| Molecular Formula | C32H30O14 |
| Purity | >98% by HPLC |
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Description
It is a symmetric dimer antibiotic isolated from an uncharacterised species of penicillium. It displays significant antibacterial activity against a wide range of gram-positive bacteria.
Specification
| Synonyms | (4R,4'R,4aR,4'AR,7R)-Rel-2,2',3,3',4,4',9,9'-Octahydro-1,1',4,4',8,8'-Hexahydroxy-6,6'-Dimethyl-9,9'-Dioxo-[7,7'-Bi-4aH-Xanthene]-4a,4'A-Dicarboxylic Acid Dimethyl Ester |
| Storage | Store at -20°C |
| IUPAC Name | methyl 4,8,9-trihydroxy-6-methyl-1-oxo-7-(1,5,9-trihydroxy-10a-methoxycarbonyl-3-methyl-8-oxo-6,7-dihydro-5H-xanthen-2-yl)-3,4-dihydro-2H-xanthene-4a-carboxylate |
| Canonical SMILES | CC1=CC2=C(C(=C1C3=C(C4=C(C=C3C)OC5(C(CCC(=O)C5=C4O)O)C(=O)OC)O)O)C(=C6C(=O)CCC(C6(O2)C(=O)OC)O)O |
| InChI | InChI=1S/C32H30O14/c1-11-9-15-21(27(39)23-13(33)5-7-17(35)31(23,45-15)29(41)43-3)25(37)19(11)20-12(2)10-16-22(26(20)38)28(40)24-14(34)6-8-18(36)32(24,46-16)30(42)44-4/h9-10,17-18,35-40H,5-8H2,1-4H3 |
| InChI Key | FCBFXINPLHGRFE-UHFFFAOYSA-N |
| Source | Penicillium sp. |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 876.0±65.0°C at 760 mmHg |
| Density | 1.7±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. A twist of nature--the significance of atropisomers in biological systems
Jamie E Smyth, Nicholas M Butler, Paul A Keller Nat Prod Rep . 2015 Nov;32(11):1562-83. doi: 10.1039/c4np00121d.
Recently identified natural atropisomeric compounds with potential medicinal applications are presented. The ability of natural receptors to possess differential binding between atropisomers is an important factor when considering active and inactive atropisomeric drugs, and has required the development of new techniques for atropselective synthesis of desired targets. Advances in this field therefore have significant relevance to modern pharmaceutical and medicinal chemistry. The atropisomeric natural products discussed include hibarimicinone, flavomannins, talaromannins, viriditoxin, rugulotrosin A, abyssomicin C, marinopyrroles, dixiamycins, streptorubin B, ustiloxins A-F, haouamine A, bisnicalaterines, and tedarene B, all of which show significant potential as leads in antibiotic, antiviral and anticancer studies. The importance for the development of common practices regarding atropisomer recognition and classification is also emphasized.
2. Atropselective syntheses of (-) and (+) rugulotrosin A utilizing point-to-axial chirality transfer
John A Porco Jr, Robert J Capon, Richard P Johnson, Zeinab G Khalil, Sarah L Skraba-Joiner, Tian Qin Nat Chem . 2015 Mar;7(3):234-40. doi: 10.1038/nchem.2173.
Chiral, dimeric natural products containing complex structures and interesting biological properties have inspired chemists and biologists for decades. A seven-step total synthesis of the axially chiral, dimeric tetrahydroxanthone natural product rugulotrosin A is described. The synthesis employs a one-pot Suzuki coupling/dimerization to generate the requisite 2,2'-biaryl linkage. Highly selective point-to-axial chirality transfer was achieved using palladium catalysis with achiral phosphine ligands. Single X-ray crystal diffraction data were obtained to confirm both the atropisomeric configuration and absolute stereochemistry of rugulotrosin A. Computational studies are described to rationalize the atropselectivity observed in the key dimerization step. Comparison of the crude fungal extract with synthetic rugulotrosin A and its atropisomer verified that nature generates a single atropisomer of the natural product.
3. Asymmetric Synthesis of Rugulotrosin A
Haibing He, Jianhua Chen, Shuanhu Gao, Yayue Li, Zheming Xiao Org Lett . 2020 Feb 21;22(4):1485-1489. doi: 10.1021/acs.orglett.0c00063.
A new approach was developed to construct the tetrahydroxanthone by a Knoevenagel condensation/6π-electronic cyclization/aromatization cascade starting from readily available cyclohexane-1,3-diones and unsaturated aldehydes. This strategy provides a new solution for the preparation of monomeric tetrahydroxanthones bearing different functional groups at C-12. As a synthetic application, the asymmetric formal synthesis of rugulotrosin A was achieved.
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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 ╳
