Spirofungin B
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02931 |
| CAS | 214143-46-1 |
| 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,6R,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; 2,6,8-Decatrienoic acid, 10-[(2R,3S,6R,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,6R,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-VRZOSVEZSA-N |
Properties
| Antibiotic Activity Spectrum | Fungi; Yeast |
Reference Reading
1. 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).
2. 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.
3. Asymmetric total synthesis of (-)-spirofungin A and (+)-spirofungin B
Takeshi Shimizu, Tomoharu Satoh, Katsunori Murakoshi, Mikiko Sodeoka Org Lett. 2005 Dec 8;7(25):5573-6. doi: 10.1021/ol052039k.
[chemical reaction: see text]. The stereocontrolled total synthesis of (-)-spirofungin A (1) and (+)-spirofungin B (2a), polyketide-type antibiotics having various antifungal activities, has been achieved employing the Weinreb amide 8, the alkyne 9, and the vinyl boronate 5 readily available from the common intermediate 10. The first synthesis proceeded with a longest linear sequence of 31 steps, affording (-)-1 and (+)-2a in 7.9% and 5.2% overall yields, respectively.
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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 ╳
