G3Y422 · YAND_ASPNA
- ProteinShort chain dehydrogenase yanD
- GeneyanD
- StatusUniProtKB reviewed (Swiss-Prot)
- Amino acids330 (go to sequence)
- Protein existenceEvidence at protein level
- Annotation score3/5
Function
function
Short chain dehydrogenase; part of the gene cluster that mediates the biosynthesis of yanuthone D, a fungal isoprenoid epoxycyclohexenone that acts as an antibiotic against fungi and bacteria (PubMed:24684908).
The first step of the pathway is the synthesis of 6-methylsalicylic acid (6-MSA) by the polyketide synthase yanA (PubMed:24684908).
6-MSA is then converted to m-cresol by the decarboxylase yanB (PubMed:24684908).
The cytochrome P450 monooxygenase yanC then catalyzes the oxidation of m-cresol to toluquinol (PubMed:24684908).
Epoxidation of toluquinol is then performed by the short chain dehydrogenase yanD, with the help of yanE, and a further prenylation by yanG leads to 7-deacetoxyyanuthone A (PubMed:24684908).
The next step is the hydroxylation of C-22 of 7-deacetoxyyanuthone A by the cytochrome P450 monooxygenase yanH to yield 22-deacetylyanuthone A (PubMed:24684908).
O-Mevalon transferase yanI then attaches mevalon to the hydroxyl group of 22-deacetylyanuthone A to produce yanuthone E (PubMed:24684908).
Finally, the FAD-dependent monooxygenase yanF oxidizes the hydroxyl group at C15 of yanuthone E to form yanuthone D (PubMed:24684908).
Furthermore, several branching points in the pathway lead to the production of yanuthones F and G from 7-deacetoxyyanuthone A; yanuthones H and I from 22-deacetylyanuthone A; and yanuthone J from yanuthone E (PubMed:24684908).
YanD is also involved in the synthesis of yanuthone X1 which does not have 6-methylsalicylic acid (6-MSA) as precursor (PubMed:24684908).
The first step of the pathway is the synthesis of 6-methylsalicylic acid (6-MSA) by the polyketide synthase yanA (PubMed:24684908).
6-MSA is then converted to m-cresol by the decarboxylase yanB (PubMed:24684908).
The cytochrome P450 monooxygenase yanC then catalyzes the oxidation of m-cresol to toluquinol (PubMed:24684908).
Epoxidation of toluquinol is then performed by the short chain dehydrogenase yanD, with the help of yanE, and a further prenylation by yanG leads to 7-deacetoxyyanuthone A (PubMed:24684908).
The next step is the hydroxylation of C-22 of 7-deacetoxyyanuthone A by the cytochrome P450 monooxygenase yanH to yield 22-deacetylyanuthone A (PubMed:24684908).
O-Mevalon transferase yanI then attaches mevalon to the hydroxyl group of 22-deacetylyanuthone A to produce yanuthone E (PubMed:24684908).
Finally, the FAD-dependent monooxygenase yanF oxidizes the hydroxyl group at C15 of yanuthone E to form yanuthone D (PubMed:24684908).
Furthermore, several branching points in the pathway lead to the production of yanuthones F and G from 7-deacetoxyyanuthone A; yanuthones H and I from 22-deacetylyanuthone A; and yanuthone J from yanuthone E (PubMed:24684908).
YanD is also involved in the synthesis of yanuthone X1 which does not have 6-methylsalicylic acid (6-MSA) as precursor (PubMed:24684908).
Biotechnology
Yanuthone D is an antibiotic against C.albicans, methicillin-resistant S.aureus (MRSA), and vancomycin-resistant Enterococcus (PubMed:11031048).
Pathway
Secondary metabolite biosynthesis; terpenoid biosynthesis.
Features
Showing features for binding site, active site.
Type | ID | Position(s) | Description | |||
---|---|---|---|---|---|---|
Binding site | 57 | NADP+ (UniProtKB | ChEBI) | ||||
Sequence: K | ||||||
Binding site | 86 | NADP+ (UniProtKB | ChEBI) | ||||
Sequence: D | ||||||
Binding site | 113 | NADP+ (UniProtKB | ChEBI) | ||||
Sequence: N | ||||||
Active site | 204 | Proton donor | ||||
Sequence: Y | ||||||
Binding site | 204 | NADP+ (UniProtKB | ChEBI) | ||||
Sequence: Y | ||||||
Active site | 208 | Lowers pKa of active site Tyr | ||||
Sequence: K | ||||||
Binding site | 208 | NADP+ (UniProtKB | ChEBI) | ||||
Sequence: K |
GO annotations
Aspect | Term | |
---|---|---|
Molecular Function | oxidoreductase activity | |
Biological Process | terpenoid biosynthetic process |
Keywords
- Molecular function
- Ligand
Enzyme and pathway databases
Names & Taxonomy
Protein names
- Recommended nameShort chain dehydrogenase yanD
- EC number
- Alternative names
Gene names
Organism names
- Strain
- Taxonomic lineageEukaryota > Fungi > Dikarya > Ascomycota > Pezizomycotina > Eurotiomycetes > Eurotiomycetidae > Eurotiales > Aspergillaceae > Aspergillus > Aspergillus subgen. Circumdati
Accessions
- Primary accessionG3Y422
Proteomes
PTM/Processing
Features
Showing features for chain.
Type | ID | Position(s) | Description | |||
---|---|---|---|---|---|---|
Chain | PRO_0000436763 | 1-330 | Short chain dehydrogenase yanD | |||
Sequence: MVKFFQPKIDPLPTGIDLTGKTAVITGASAGMGLEVTKQLLRLRLSTAILAVRNVTKGEACIKSLLQDRGIQTHNPKPTIKVMELDMDRYDSVQQFAKTLREEVPVVDLLILNAGVASLNFERSPSGHERVTQVNYCSNVLLVAELLPHLEAGAEQTGSPARISWVGSRSHETPSFEKKAPIEADEGVLEHMDKEEAFVPFQRYNDTKLLCVLFLYSLAPRLDPKKVVINTMCPGMVNTGMSNMLPLHLRLIFNVIKAIRARPVEVGGWIILNAALVAGPESHGKFLADKTITDKSAIVTSPMGQDIQKKLWEETITEMSKLTTLPPQFR |
Interaction
Protein-protein interaction databases
Structure
Sequence
- Sequence statusComplete
- Length330
- Mass (Da)36,447
- Last updated2016-07-06 v2
- ChecksumA7A5995BDD1CB403