Cladospolide D
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| Category | Antibiotics |
| Catalog number | BBF-00354 |
| CAS | 371229-61-7 |
| Molecular Weight | 226.27 |
| Molecular Formula | C12H18O4 |
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Description
It is produced by the strain of Cladosporium sp. FT-0012. Cladospolide D has the activity against part of fungi.
Specification
| IUPAC Name | (3E)-6-hydroxy-12-methyl-1-oxacyclododec-3-ene-2,5-dione |
| Canonical SMILES | CC1CCCCCC(C(=O)C=CC(=O)O1)O |
| InChI | InChI=1S/C12H18O4/c1-9-5-3-2-4-6-10(13)11(14)7-8-12(15)16-9/h7-10,13H,2-6H2,1H3/b8-7+ |
| InChI Key | OFRQIORIBGXHBF-BQYQJAHWSA-N |
Properties
| Appearance | Colorless Oil |
| Antibiotic Activity Spectrum | fungi |
Reference Reading
1. Cladospolide D, a new 12-membered macrolide antibiotic produced by Cladosporium sp. FT-0012
H Zhang, H Tomoda, N Tabata, H Miura, M Namikoshi, Y Yamaguchi, R Masuma, S Omura J Antibiot (Tokyo). 2001 Aug;54(8):635-41. doi: 10.7164/antibiotics.54.635.
A new antibiotic termed cladospolide D was isolated along with the known cladospolides A and B from the fermentation broth of Cladosporium sp. FT-0012 by solvent extraction, ODS column chromatography and preparative HPLC. The structure of cladospolide D was deduced to be (E)-2-dodecen-5-hydroxy-11-olide-4-one. Cladospolide D showed antifungal activity against Pyricularia oryzae and Mucor racemosus.
2. A chemoenzymatic total synthesis of the phytotoxic undecenolide (-)-cladospolide A
Martin G Banwell, David T J Loong Org Biomol Chem. 2004 Jul 21;2(14):2050-60. doi: 10.1039/b401829j. Epub 2004 Jun 23.
An eleven-step synthesis of the title compound (1) from biocatalytically-derived and enantiomerically pure 'building blocks' alcohol (R)-(-)-9 and ester 13 is described. Attempts to construct the twelve-membered lactone ring of cladospolide A in a direct manner by using a ring-closing metathesis (RCM) reaction failed. However, a ten-membered lactone 19, could be constructed by such means and this was then subject to a two-carbon homologation sequence involving, inter alia, Wadsworth-Horner-Emmons and Yamaguchi lactonisation reactions in the closing stages of the synthesis. The impact of substituent stereochemistries and protecting groups on the RCM reaction leading to various ten-membered lactones is also described.
3. De novo asymmetric synthesis of cladospolide B-D: structural reassignment of cladospolide D via the synthesis of its enantiomer
Yalan Xing, George A O'Doherty Org Lett. 2009 Mar 5;11(5):1107-10. doi: 10.1021/ol9000119.
The enantioselective synthesis of cladospolide B, C, and (ent)-cladospolide D has been achieved in 11-15 steps from 1-nonyne. The route relies upon an alkyne zipper reaction to relay an ynone and dienoate functional groups across a nine carbon fragment, which enables a highly enantioselective Noyori ynone reduction and a diastereo- and regioselective Sharpless dihydroxylation of a dienoate. In addition to being a flexible approach to three members of the cladospolide natural products, this route for the first time correctly established the structure for cladospolide D.
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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 ╳
