BE-43472B
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| Category | Antibiotics |
| Catalog number | BBF-05008 |
| CAS | 180027-59-2 |
| Molecular Weight | 552.53 |
| Molecular Formula | C32H24O9 |
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Description
BE-43472B is a bisanthraquinone antibiotic isolated from a streptomycete strain. It has antibacterial activity against MSSA, MRSA, TRSA and VRE.
Specification
| Synonyms | (8S,9S,9aR,18aS,20R)-8,9-Dihydro-4,6,8,16-tetrahydroxy-8,14,20-trimethyl-18a,9-(epoxymethano)-18aH-dianthra[1,2-b:4'a,10'-d]furan-5,12,17(7H)-trione; 18a,9-(Epoxymethano)-18aH-dianthra[1,2-b:4'a,10'-d]furan-5,12,17(7H)-trione, 8,9-dihydro-4,6,8,16-tetrahydroxy-8,14,20-trimethyl-, (8S,9S,9aR,18aS,20R)- |
| IUPAC Name | (7bR,8S,9S,16bS,20R)-1,9,12,13-tetrahydroxy-3,9,20-trimethyl-9,10-dihydro-16b,8-(epoxymethano)dianthra[1,2-b:4a',10'-d]furan-5,11,18(8H)-trione |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 880.6±65.0°C (Predicted) |
| Melting Point | >250°C |
| Density | 1.69±0.1 g/cm3 (Predicted) |
Reference Reading
1. Total synthesis and absolute configuration of the bisanthraquinone antibiotic BE-43472B
K C Nicolaou, Yee Hwee Lim, Jochen Becker Angew Chem Int Ed Engl. 2009;48(19):3444-8. doi: 10.1002/anie.200900058.
An-T-biotic: The first total synthesis of the T-shaped bisanthraquinone natural product BE-43472B was accomplished and its absolute configuration assigned. Key transformations in the pivotal cascade sequence include a Diels-Alder reaction, a hemiketal formation, and a nucleophilic aromatic ipso substitution.
2. Total synthesis and biological evaluation of (+)- and (-)-bisanthraquinone antibiotic BE-43472B and related compounds
K C Nicolaou, Jochen Becker, Yee Hwee Lim, Alexandre Lemire, Thomas Neubauer, Ana Montero J Am Chem Soc. 2009 Oct 21;131(41):14812-26. doi: 10.1021/ja9073694.
The bisanthraquinone antibiotic BE-43472B [(+)-1] was isolated by Rowley and co-workers from a streptomycete strain found in a blue-green algae associated with the ascidian Ecteinascidia turbinata and has shown promising antibacterial activity against clinically derived isolates of methicillin-susceptible, methicillin-resistant, and tetracyclin-resistant Staphylococcus aureus (MSSA, MRSA, and TRSA, respectively) and vancomycin-resistant Enterococcus faecalis (VRE). Described herein is the first total synthesis of both enantiomers of this bisanthraquinone antibiotic, the determination of its absolute configuration, and the biological evaluation of these and related compounds. The developed synthesis relies on a highly efficient cascade sequence involving an intermolecular Diels-Alder reaction between diene (R)-61 and dienophile 55, followed by an intramolecular nucleophilic aromatic ipso substitution. Late-stage transformations included a remarkable photochemical alpha,beta-epoxyketone rearrangement [80 --> (+)-1]. Interestingly, the unnatural enantiomer [(-)-1] of antibiotic BE-43472B exhibited antibacterial properties comparable to those of the natural enantiomer [(+)-1].
3. Origins of regioselectivity of Diels-Alder reactions for the synthesis of bisanthraquinone antibiotic BE-43472B
Amy E Hayden, Robert S Paton, Jochen Becker, Yee Hwee Lim, K C Nicolaou, K N Houk J Org Chem. 2010 Feb 5;75(3):922-8. doi: 10.1021/jo902572y.
The regioselectivities of several Diels-Alder reactions utilized en route to bisanthraquinone antibiotic BE-43472B are examined using density functional theory calculations. These reactions involve highly substituted dienes and juglone dienophiles, and there is an opposite regiochemical outcome for Diels-Alder reactions with beta-aryl substituted juglones when compared to reactions of unsubstituted juglone. In this article, the effect of an aromatic conjugating group bonded to juglone is explored.
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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 ╳
