Spirofungin A
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| Category | Antibiotics |
| Catalog number | BBF-02930 |
| CAS | 214143-44-9 |
| Molecular Weight | 502.64 |
| Molecular Formula | C29H42O7 |
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Description
It is produced by the strain of Str. violaceusniger Tü 4113. It has strong anti-yeast activity and moderate anti-filamentous fungus effect, but it has no effect against Gram-positive and Gram-negative bacteria.
Specification
| Synonyms | (2E,6E,8E)-(4S,5S)-10-[(2R,3S,6S,8R,9S)-8-((1E,3E)-4-Carboxy-3-methyl-buta-1,3-dienyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-5-hydroxy-4,8-dimethyl-deca-2,6,8-trienoic acid; (-)-spirofungin A; 2,6,8-Decatrienoic acid, 10-[(2R,3S,6S,8R,9S)-8-[(1E,3E)-4-carboxy-3-methyl-1,3-butadienyl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undec-2-yl]-5-hydroxy-4,8-dimethyl-, (2E,4S,5S,6E,8E)- |
| IUPAC Name | (2E,4S,5S,6E,8E)-10-[(2R,3S,6S,8R,9S)-2-[(1E,3E)-4-carboxy-3-methylbuta-1,3-dienyl]-3,9-dimethyl-1,7-dioxaspiro[5.5]undecan-8-yl]-5-hydroxy-4,8-dimethyldeca-2,6,8-trienoic acid |
| Canonical SMILES | CC1CCC2(CCC(C(O2)C=CC(=CC(=O)O)C)C)OC1CC=C(C)C=CC(C(C)C=CC(=O)O)O |
| InChI | InChI=1S/C29H42O7/c1-19(6-10-24(30)21(3)9-13-27(31)32)7-11-25-22(4)14-16-29(35-25)17-15-23(5)26(36-29)12-8-20(2)18-28(33)34/h6-10,12-13,18,21-26,30H,11,14-17H2,1-5H3,(H,31,32)(H,33,34)/b10-6+,12-8+,13-9+,19-7+,20-18+/t21-,22-,23-,24-,25+,26-,29-/m0/s1 |
| InChI Key | ZUPXAYGYALHVSA-ZTRNFXHBSA-N |
Properties
| Antibiotic Activity Spectrum | Fungi; Yeast |
Reference Reading
1. Enantioselective total synthesis of spirofungins A and B
Michael T Crimmins, Elizabeth A O'Bryan Org Lett. 2010 Oct 1;12(19):4416-9. doi: 10.1021/ol101961c.
The enantioselective total synthesis of spirofungins A (1) and B (2) is reported in 14 steps over the longest linear sequence. Key steps include the use of thiazolidinethione-mediated aldol reactions to assemble the major fragments and installation of the C1-C6 side chain using a cross metathesis reaction.
2. Stereoselective total synthesis of (-)-spirofungin A by utilising hydrogen-bond controlled spiroketalisation
John E Lynch, Shannon D Zanatta, Jonathan M White, Mark A Rizzacasa Chemistry. 2011 Jan 3;17(1):297-304. doi: 10.1002/chem.201002501. Epub 2010 Dec 10.
The stereoselective total synthesis of the spiroketal containing Streptomyces metabolite (-)-spirofungin A (1) is described. A key step involved a spiroketalisation controlled by an intramolecular H-bond which favoured the desired spiroketal 4 (13:1 ratio). The presence of the intramolecular H-bond in 4 is possibly due to a 1,5-alkyne-oxygen interaction. Other key steps include an efficient cross-metathesis to form the spiroketal precursor, a tin mediated syn-aldol reaction and a Stille cross-coupling reaction to create the C22C23 bond. A final Wittig extension followed by deprotection gave (-)-spirofungin A (1).
3. Synthetic studies of biologically active natural products contributing to pesticide development
Hiromasa Kiyota J Pestic Sci. 2020 Aug 20;45(3):177-183. doi: 10.1584/jpestics.J20-03.
Natural product research, including total synthesis, is becoming increasingly important for the discovery of pesticide seeds and leads. Synthetic studies of biologically active compounds such as antibiotics (enacyloxins, polynactin, pamamycins, spirofungin A and B, glutarimides and antimycins), phytopathogenic toxins (pyricuol, pyriculariol, tabtoxinine-β-lactam, gigantenone, phomenone and phaseolinone), marine derived products (pteroenone, β-D-Asp-Gly, didemniselinolipid B, cortistatin A, sanctolide A and gizzerosine), POPs (dieldrin, endosulfan, HCB), plant hormones (abscisic acid and jasmonic acid), insect pheromones (endo-brevicomin etc.), especially using a variety of biotransformation are described.
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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 ╳
