Aflastatin A
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| Category | Mycotoxins |
| Catalog number | BBF-00387 |
| CAS | 179729-59-0 |
| Molecular Weight | 1258.56 |
| Molecular Formula | C62H115NO24 |
| Purity | ≥ 95% |
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Description
It is produced by the strain of Streptomyces sp. MRI 142. Aflatoxin A has anti-Gram-positive bacteria, Pyricularia oryzae and yeast activity (MIC is 0.19-0.39 µg/mL), and inhibits the growth of adenocarcinoma 755 (1.0 mg/kg reduces tumor growth by 75% the above).
Specification
| Synonyms | 2,4-Pyrrolidinedione, 1,5-dimethyl-3-(1,8,9,11,13,15,17,19,21,23,25,27,28,29,30,31-hexadecahydroxy-2,4,6,10,12,14,18,20-octamethyl-32-(tetrahydro-3,4,5,6-tetrahydroxy-6-(2-hydroxyundecyl)-2H-pyran-2-yl)-2-dotriacontenylidene)-; LS-137668 |
| Storage | -20 °C |
| IUPAC Name | (3E,5R)-3-[(E,4S,6R,8S,9S,10S,11R,12R,13R,14S,15R,17S,18S,19R,20S,21R,23R,25S,27S,28R,29S,30S,31R)-1,8,9,11,13,15,17,19,21,23,25,27,28,29,30,31-hexadecahydroxy-2,4,6,10,12,14,18,20-octamethyl-32-[(2R,3S,4S,5S,6S)-3,4,5,6-tetrahydroxy-6-[(2R)-2-hydroxyundecyl]oxan-2-yl]dotriacont-2-enylidene]-1,5-dimethylpyrrolidine-2,4-dione |
| Canonical SMILES | CCCCCCCCCC(CC1(C(C(C(C(O1)CC(C(C(C(C(CC(CC(CC(C(C)C(C(C)C(CC(C(C)C(C(C)C(C(C)C(C(CC(C)CC(C)C=C(C)C(=C2C(=O)C(N(C2=O)C)C)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O)O |
| InChI | InChI=1S/C62H115NO24/c1-12-13-14-15-16-17-18-19-38(64)28-62(86)60(84)59(83)57(81)47(87-62)27-46(72)56(80)58(82)55(79)45(71)25-40(66)23-39(65)24-41(67)32(5)50(74)33(6)42(68)26-43(69)34(7)51(75)35(8)52(76)36(9)53(77)44(70)22-30(3)20-29(2)21-31(4)49(73)48-54(78)37(10)63(11)61(48)85/h21,29-30,32-47,50-53,55-60,64-77,79-84,86H,12-20,22-28H2,1-11H3/b31-21+,49-48+/t29-,30+,32-,33-,34-,35+,36-,37+,38+,39+,40-,41+,42-,43+,44-,45-,46+,47+,50+,51+,52+,53-,55+,56-,57+,58-,59-,60-,62-/m0/s1 |
| InChI Key | VAQYWUJSXJULKR-YLMXTBCDSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; yeast |
| Solubility | Soluble in DMSO, Methanol, Water, Pyridine, Ethanol |
Reference Reading
1. Synthesis of C3-C21 Segment of Aflastatin A Using Remote Asymmetric Induction Reactions
Sawato Murakoshi, Seijiro Hosokawa Org Lett. 2019 Feb 1;21(3):758-761. doi: 10.1021/acs.orglett.8b04008. Epub 2019 Jan 11.
The C3-C21 segment of aflastatin A has been synthesized by converging three segments including the C3-C8 segment, the C9-C15 segment, and the C16-C21 segment. Each segment has been synthesized from a vinylketene silyl N,O-acetal possessing a chiral auxiliary by a wide-range stereocontrol strategy. The C3-C8 segment was constructed in seven steps including the stereoselective vinylogous Mukaiyama alkylation, while the C9-C15 segment and the C16-C21 segment were synthesized using the vinylogous Mukaiyama aldol reaction in seven and eight steps, respectively.
2. A [Pd]-mediated ω-alkynone cycloisomerization approach for the central tetrahydropyran unit and the synthesis of C(31)-C(48) fragment of aflastatin A
Sachin B Narute, Neella Chandra Kiran, Chepuri V Ramana Org Biomol Chem. 2011 Aug 7;9(15):5469-75. doi: 10.1039/c1ob05251a. Epub 2011 Jun 14.
A concise assembly of the central tetrahydropyran unit of aflastatin A featuring a Pd-mediated alkynone cycloisomerization to provide a glycal and its subsequent stereoselective hydroboration to deliver the requisite stereochemistry at C(33) and C(34) centers is documented.
3. Total Synthesis of Aflastatin A
David A Evans, Jason J Beiger, Jason D Burch, Peter H Fuller, Frank Glorius, Egmont Kattnig, David A Thaisrivongs, William C Trenkle, Joseph M Young, Jing Zhang J Am Chem Soc. 2022 Nov 2;144(43):19953-19972. doi: 10.1021/jacs.2c08244. Epub 2022 Oct 21.
The total syntheses of aflastatin A and its C3-C48 degradation fragment (6a, R = H) have been accomplished. The syntheses feature several complex diastereoselective fragment couplings, including a Felkin-selective trityl-catalyzed Mukaiyama aldol reaction, a chelate-controlled aldol reaction involving soft enolization with magnesium, and an anti-Felkin-selective boron-mediated oxygenated aldol reaction. Careful comparison of the spectroscopic data for the synthetic C3-C48 degradation fragment to that reported by the isolation group revealed a structural misassignment in the lactol region of the naturally derived degradation product. Ultimately, the data reported for the naturally derived aflastatin A C3-C48 degradation lactol (6a, R = H) were attributed to its derivative lactol trideuteriomethyl ether (6c, R = CD3). Additionally, the revised absolute configurations of six stereogenic centers (C8, C9, and C28-C31) were confirmed.
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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 ╳
