Aplasmomycin
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| Category | Antibiotics |
| Catalog number | BBF-00061 |
| CAS | 61230-25-9 |
| Molecular Weight | 798.69 |
| Molecular Formula | C40H60BNaO14 |
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Description
Aplasmomycin A is an antibiotic with antimalarial activity isolated from Streptomycete. Aplasmomycin has the activity of inhibiting gram-positive bacteria and mycobacteria, and has anti-protozoal effects.
Specification
| Synonyms | Aplasmomycin A |
| IUPAC Name | sodium;(1R,2R,5S,6R,8S,9E,12R,14S,17R,18R,22R,25S,26R,28S,29E,32R,34S,37R)-12,32-dihydroxy-6,13,13,17,26,33,33,37-octamethyl-4,7,19,21,24,27,38,39,41,42-decaoxa-20-boranuidaoctacyclo[18.17.1.11,34.12,20.15,8.114,18.125,28.018,22]tritetraconta-9,29-diene-3,23-dione |
| Canonical SMILES | [B-]123OC4C(=O)OC5CC(C=CCC(C(C6CCC(C(O1)(O6)C(O2)C(=O)OC7CC(C=CCC(C(C8CCC(C4(O3)O8)C)(C)C)O)OC7C)C)(C)C)O)OC5C.[Na+] |
| InChI | InChI=1S/C40H60BO14.Na/c1-21-15-17-31-37(5,6)29(42)13-9-11-26-20-28(24(4)47-26)49-36(45)34-40-22(2)16-18-32(51-40)38(7,8)30(43)14-10-12-25-19-27(23(3)46-25)48-35(44)33-39(21,50-31)54-41(52-33,53-34)55-40;/h9-12,21-34,42-43H,13-20H2,1-8H3;/q-1;+1/b11-9+,12-10+;/t21-,22-,23-,24-,25-,26-,27+,28+,29-,30-,31+,32+,33+,34+,39+,40+,41?;/m1./s1 |
| InChI Key | GEIYDRPAWIMINR-ZDKANEFWSA-N |
Properties
| Appearance | Needle Crystals |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria; parasites |
| Melting Point | 283-285°C |
Reference Reading
1. Total synthesis of macrodiolide ionophores aplasmomycin A and boromycin via double ring contraction
Mitchell A Avery, Satish C Choudhry, Om Prakash Dhingra, Brian D Gray, Myung-chol Kang, Shen-chun Kuo, Thalathani R Vedananda, James D White, Alan J Whittle Org Biomol Chem. 2014 Dec 7;12(45):9116-32. doi: 10.1039/c4ob01017e.
The half structure of the symmetrical macrodiolide aplasmomycin A was synthesized by alkylation of a C3-C10 α-sulfonyl ketone subunit, prepared from (R)-pulegone and protected as a C3 ortholactone with (2R,3R)-butanediol, by a protected 15,16-dihydroxy (12E)-allylic chloride representing C11-C17. The latter was obtained from (2S,3R)-1,2-epoxy-3-butanol and propargyl alcohol. Regio- and stereoselective 5-exo-trig cyclization of the ene diol moiety in this segment, mediated by N-bromosuccinimide, led to the (2R,3S,5R)-tetrahydrofuran substructure of aplasmomycin A. Attachment of an α-acetic ester at the C3 carboxylic acid and esterification of the 3'-hydroxyl group of the tetrahydrofuran as its α-bromoacetate enabled coupling of two aplasmomycin half structures as an α-acyloxy acetate. Mukaiyama macrolactonization of this hydroxy acid afforded a symmetrical 36-membered diolide. Base-mediated double Chan rearrangement of this bis α-acyloxy dilactone caused ring contraction to the 34-membered macrocycle of desboroaplasmomycin A while generating the transannular 2-hydroxy-3-hemiketal motif of the natural product in the correct configuration. Final incorporation of boron into the tetraol core produced aplasmomycin A, isolated as its sodium borate. Extension of this route to the unsymmetrical macrodiolide boromycin was accomplished by modifications that included reversal of C12-C13 olefin geometry to (Z) for the southern half structure along with stereoselective hydride reductions of the C9 ketone that produced (9R) and (9S) alcohols for northern and southern half structures, respectively. Coupling of these half structures was made using an α-acyloxy ester linkage as for aplasmomycin A, but ring closure in this case was orchestrated via a blocked C16 alcohol that left open the C15 hydroxyl group of the southern half for Mukaiyama macrolactonization. A double Chan rearrangement of the resulting 35-membered macrocycle produced the 33-membered diolide of desborodesvalinylboromycin which had been obtained previously by degradation of natural boromycin. Insertion of boron into the tetraol core followed by esterification of the C16 alcohol with a masked d-valine and final deprotection furnished boromycin as its zwitterionic (Böeseken) complex.
2. Aplasmomycin and boromycin are specific inhibitors of the futalosine pathway
Yohei Shimizu, Yasushi Ogasawara, Atsuko Matsumoto, Tohru Dairi J Antibiot (Tokyo). 2018 Nov;71(11):968-970. doi: 10.1038/s41429-018-0087-2. Epub 2018 Aug 8.
We searched for specific inhibitors of the futalosine pathway, non-canonical pathway of menaquinone biosynthesis operating in Helicobacter pylori, from metabolites produced by actinomycetes. Aplasmomycin, a boron-containing macrodiolide, was isolated from Streptomyces sp. K15-0223 as a specific inhibitor of the futalosine pathway. We also showed boromycin, an analog of aplasmomycin, had similar activity.
3. Boron NMR as a Method to Screen Natural Product Libraries for B-Containing Compounds
Jocelyn M Macho, Riley M Blue, Hsiau-Wei Lee, John B MacMillan Org Lett. 2022 May 6;24(17):3161-3166. doi: 10.1021/acs.orglett.2c00885. Epub 2022 Apr 26.
Natural products are biologically relevant metabolites exploited for biomedicine and biotechnology. The frequent reisolation of known natural products questions whether existing discovery models are still capable of identifying novel compounds. As innovative NMR-based screening techniques can help overcome these challenges, we applied a phase cycling composite pulse sequence to 11B NMR experiments to enhance their sensitivity to screen libraries for novel boron-containing molecules. Aplasmomycin and autoinducer-2 were detected in crude and enhanced microbial fractions, via their boron signals, as proof of concept. Subsequently, a screen of 21 crude plant and 50 crude marine microbial extracts were chosen at random and analyzed with the optimized 11B experiment for feasibility as a high throughput discovery method. Eight of the plant samples and 13 of the microbial samples were identified as boron-containing, suggesting that there is a higher presence of boron metabolites available from natural sources than previously known due to a lack of appropriate discovery methods. As a result, we believe that this optimized 11B NMR experiment can serve as a robust method for quick and facile discovery of novel boron-containing metabolites from a variety of natural sources.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
