Alternapyrone
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| Category | Others |
| Catalog number | BBF-04667 |
| CAS | 676340-02-6 |
| Molecular Weight | 428.65 |
| Molecular Formula | C28H44O3 |
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Description
Alternapyrone is a polyketide produced in A. oryzae heterologously expressing the A. solani-derived polyketide synthase gene alt5.
Specification
| IUPAC Name | 4-hydroxy-3,5-dimethyl-6-[(4E,6E,12E)-4,6,8,12,14-pentamethylhexadeca-4,6,12-trien-2-yl]pyran-2-one |
| Canonical SMILES | CCC(C)C=C(C)CCCC(C)C=C(C)C=C(C)CC(C)C1=C(C(=C(C(=O)O1)C)O)C |
| InChI | InChI=1S/C28H44O3/c1-10-18(2)14-19(3)12-11-13-20(4)15-21(5)16-22(6)17-23(7)27-24(8)26(29)25(9)28(30)31-27/h14-16,18,20,23,29H,10-13,17H2,1-9H3/b19-14+,21-15+,22-16+ |
| InChI Key | ZPFTUJZLXSKBKE-NZDFSFLRSA-N |
Properties
| Appearance | Solid |
Reference Reading
1. C-Methylation controls the biosynthetic programming of alternapyrone
Jaiyfungkhong Phakeovilay, Witcha Imaram, Supachai Vuttipongchaikij, Waraporn Bunnak, Colin M Lazarus, Pakorn Wattana-Amorn Org Biomol Chem. 2022 Jun 29;20(25):5050-5054. doi: 10.1039/d2ob00947a.
Alternapyrone is a highly methylated polyene α-pyrone biosynthesised by a highly reducing polyketide synthase. Mutations of the catalytic dyad residues, H1578A/Q and E1604A, of the C-methyltransferase domain resulted in either significantly reduced or no production of alternapyrone, indicating the importance of C-methylation for alternapyrone biosynthesis.
2. Bioinformatics Prediction of Polyketide Synthase Gene Clusters from Mycosphaerella fijiensis
Roslyn D Noar, Margaret E Daub PLoS One. 2016 Jul 7;11(7):e0158471. doi: 10.1371/journal.pone.0158471. eCollection 2016.
Mycosphaerella fijiensis, causal agent of black Sigatoka disease of banana, is a Dothideomycete fungus closely related to fungi that produce polyketides important for plant pathogenicity. We utilized the M. fijiensis genome sequence to predict PKS genes and their gene clusters and make bioinformatics predictions about the types of compounds produced by these clusters. Eight PKS gene clusters were identified in the M. fijiensis genome, placing M. fijiensis into the 23rd percentile for the number of PKS genes compared to other Dothideomycetes. Analysis of the PKS domains identified three of the PKS enzymes as non-reducing and two as highly reducing. Gene clusters contained types of genes frequently found in PKS clusters including genes encoding transporters, oxidoreductases, methyltransferases, and non-ribosomal peptide synthases. Phylogenetic analysis identified a putative PKS cluster encoding melanin biosynthesis. None of the other clusters were closely aligned with genes encoding known polyketides, however three of the PKS genes fell into clades with clusters encoding alternapyrone, fumonisin, and solanapyrone produced by Alternaria and Fusarium species. A search for homologs among available genomic sequences from 103 Dothideomycetes identified close homologs (>80% similarity) for six of the PKS sequences. One of the PKS sequences was not similar (< 60% similarity) to sequences in any of the 103 genomes, suggesting that it encodes a unique compound. Comparison of the M. fijiensis PKS sequences with those of two other banana pathogens, M. musicola and M. eumusae, showed that these two species have close homologs to five of the M. fijiensis PKS sequences, but three others were not found in either species. RT-PCR and RNA-Seq analysis showed that the melanin PKS cluster was down-regulated in infected banana as compared to growth in culture. Three other clusters, however were strongly upregulated during disease development in banana, suggesting that they may encode polyketides important in pathogenicity.
3. Cloning and heterologous transcription of a polyketide synthase gene from the lichen Solorina crocea
Andrey N Gagunashvili, Snorri P Davídsson, Zophonías O Jónsson, Olafur S Andrésson Mycol Res. 2009 Mar;113(Pt 3):354-63. doi: 10.1016/j.mycres.2008.11.011. Epub 2008 Dec 6.
Lichens and most ascomycete fungi produce polyketide secondary metabolites often with valuable biological activities. Their biosynthesis is primarily governed by large iterative multifunctional type I polyketide synthases. Although there has been good progress studying filamentous non-lichenized fungi, there is limited information on polyketide biosynthesis in lichens and their mycobionts, due to their slow growth, difficulties in establishing pure cultures, and the absence of methods for direct genetic manipulation. However, heterologous expression in a surrogate host offers an alternative approach for exploring lichen polyketide biosynthesis. Here, we report cloning of a type I polyketide synthase gene from the foliose lichen Solorina crocea and its heterologous transcription in the filamentous fungus Aspergillus oryzae, including processing of the transcript. No new polyketide product was detected. The lichen polyketide synthase showed greatest homology with uncharacterized genes from filamentous fungi and lower homology with proteins catalysing biosynthesis of the decaketide alternapyrone and the tetraketide side-chain of squalestatin. The technology platform utilized here presents a useful tool for functional characterization of fungal biosynthetic genes and provides a means for novel production of valuable compounds.
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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 ╳
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