Mycolactone
From Wikipedia, the free encyclopedia
 |
All or part of this article may be confusing or unclear. Please help clarify the article. Suggestions may be on the talk page. (February 2007) |
| Mycolactone | |
|---|---|
 |
|
| IUPAC name | [(6S,7S,9E,12R)-12-[(E,2S,6R,7R,9R)-7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl]-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl] (2E,4E,6E,8E,10E,12S,13S,15S)-12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate |
| Identifiers | |
| CAS number | [222050-77-3] |
| PubChem | |
| MeSH | |
| Properties | |
| Molecular formula | C44H70O9 |
| Molar mass | 743.021 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
|
Mycolactone is a polyketide-derived macrolide produced and secreted by the pathogenic mycobacteria M. ulcerans, M. liflandii, M. pseudoshottsii, and a few M. marinum isolates.
The M. ulcerans toxins comprise a family of polyketide-derived macrolides, mycolactones, which are formed through condensation of two polyketide chains. Each isolate of M. ulcerans produces a characteristic mixture of mycolactone congeners. M. ulcerans strains from different geographic areas produce distinct patterns of mycolactone congeners. The structural heterogeneity in mycolactones is due to variations in the fatty acid side chain. The structure of the core lactone is invariant.[1]
Genes for mycolactone biosynthesis form a contiguous 110-kb cluster (Fig. 1A) on a large plasmid. The lactone core is encoded by two polyketide synthase (Pks) genes, mlsA1 and mlsA2, and a third polyketide synthase gene, mlsB, encodes the fatty acid side chain. Three accessory genes are found in the mycolactone cluster. One of these, MUP053, encodes a p450 monooxygenase that is thought to produce the hydroxyl at C′-12 on the fatty acid side chain. The gene encoding a FabH-like, type III ketosynthase (KS), located upstream of mlsA1, encodes a putative “joinase” (MUP045), and a small type II thioesterase (TE II) gene (MUP037) is located between mlsA2 and mlsB.[1]
Five categories have been described so far:
- Mycolactone A/B (M. ulcerans from Africa, Malaysia, ...)
- Mycolactone C (8 Australian M. ulcerans isolates)
- Mycolactone D (M. ulcerans from Asia)
- Mycolactone E (M. liflandii)[1]
- Mycolactone F (M. pseudoshottsii and M. marinum from Israël)[2]
[edit] References
- ^ a b c Mve-Obiang A; Lee RE; Umstot ES; Trott KA; Grammer TC; Parker JM; Ranger BS; Grainger R; Mahrous EA; Small PLC (2005). "A newly discovered mycobacterial pathogen isolated from laboratory colonies of Xenopus species with lethal infections produces a novel form of mycolactone, the Mycobacterium ulcerans macrolide toxin.". Infect. Immun. 73 (6): 3307–3312. doi:. PMID 15908356.
- ^ Ranger BS; Mahrous EA; Mosi L; Adusumilli S; Lee RE; Colorni A; Rhodes M; Small PLC (2006). "Globally distributed mycobacterial fish pathogens produce a novel plasmid-encoded toxic macrolide, mycolactone F.". Infect. Immun.. doi:. PMID 16923788.
