Category:PK
From Metabolomics.JP
(Difference between revisions)
(→Non-ribosomal peptide synthase (NRPS)) |
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| Line 42: | Line 42: | ||
{| class="wikitable" | {| class="wikitable" | ||
| + | !species || Actinomycetes || Cyanobacteria || γ-Proteobacteria || Fungi || Dinoflagellates | ||
|- | |- | ||
| − | ! || | + | !Type-I PKS |
| + | | Ο || Ο || Ο || Χ || Ο | ||
|- | |- | ||
| − | ! | + | !Type-II PKS |
| − | | | + | | Ο || Χ || Χ || Ο || Χ |
|- | |- | ||
| − | ! | + | !NRPS |
| − | | | + | | Ο || Ο || Ο || Ο || Χ |
| + | |- | ||
| + | !deoxysugar | ||
| + | | Ο || Χ || Χ || Χ || Χ | ||
| + | |- | ||
| + | !Terpene | ||
| + | | Δ || Χ || Χ || Ο || Χ | ||
|} | |} | ||
===Type I PKS (non-iterative)=== | ===Type I PKS (non-iterative)=== | ||
| − | * | + | * Multi catalytic domains exist in a single protein |
| − | * | + | * Chain length is determined by the number of catalytic domains. |
| − | * | + | * Products are non-aromatic and have larger masses. |
Ref. Erythromycin biosynthesis in ''Nat Prod Rep'' '''18''', 380 (2001) | Ref. Erythromycin biosynthesis in ''Nat Prod Rep'' '''18''', 380 (2001) | ||
| Line 62: | Line 70: | ||
===Type II PKS (iterative)=== | ===Type II PKS (iterative)=== | ||
| − | * | + | * Three proteins (KSα, KSβ, ACP) are repeatedly used for carbon chain elongation. |
| − | * | + | * Chain length is determined by another protein, CLF. |
| − | * products are aromatic (e.g. chiorotetracycline, pradimicin) | + | * In bacteria, products are aromatic (e.g. chiorotetracycline, pradimicin). |
| + | * In fungi, products are both non-aromatic and aromatic. | ||
| − | ==Non-ribosomal peptide synthase (NRPS)== | + | ===Non-ribosomal peptide synthase (NRPS)=== |
Coupling with PKS and NRPS | Coupling with PKS and NRPS | ||
| Line 82: | Line 91: | ||
Ref. Dewick, PM ''Medicinal Natural Products'' (2009) | Ref. Dewick, PM ''Medicinal Natural Products'' (2009) | ||
| + | |||
| + | |||
| + | ==Decoration== | ||
| + | deoxysugars | ||
| + | |||
| + | deoxygenation, c-methylation, amination, n-methylation, ketosugar, | ||
| + | |||
| + | ==Unusual structures== | ||
| + | {| class="wikitable" | ||
| + | ! Phoma | ||
| + | | zaragozic acid, phomoidoride | ||
| + | ! Streptomyces | ||
| + | |yatakemycin, leinamycin, saframycin, neocarzinostatin, staurosporin, FR182877 | ||
| + | ! Other bacteria | ||
| + | | PKS-NRPS hybrid type | ||
| + | Curacin A (Lyngbya), Shiphonazole (Herpetosiphon), Jamaicamide A (Lyngbya), Cylindrospermopsin (Cylindrospermopsis) | ||
| + | |||
| + | |} | ||
Revision as of 09:55, 14 November 2009
Polyketide (ポリケチド)
Contents |
Class Overview
Polyketides are synthesized through the polymerization of acetyl units (β-ketomethylene chain).
| 1st Class | ||
|---|---|---|
| PK4: Four C2 Units orsellinic acid, 6-methylsalicylic acid, triacetic acid lactone, asperlin, usnic acid, methylphloracetophenone, penicillic acid, patulin |
PK5: Five C2 Units citrinin, aflatoxin, augenone, sepedonin, stipitatonic acid |
PK6: Six C2 Units plumbagin, 7-methyljuglone, juglone, variotin |
| PK7: Seven and eight C2 Units Anthraquinone rings |
PK9: Nine C2 Units Tetracyclines | |
Polyketide Synthase (PKS)
| species | Actinomycetes | Cyanobacteria | γ-Proteobacteria | Fungi | Dinoflagellates |
|---|---|---|---|---|---|
| Type-I PKS | Ο | Ο | Ο | Χ | Ο |
| Type-II PKS | Ο | Χ | Χ | Ο | Χ |
| NRPS | Ο | Ο | Ο | Ο | Χ |
| deoxysugar | Ο | Χ | Χ | Χ | Χ |
| Terpene | Δ | Χ | Χ | Ο | Χ |
Type I PKS (non-iterative)
- Multi catalytic domains exist in a single protein
- Chain length is determined by the number of catalytic domains.
- Products are non-aromatic and have larger masses.
Ref. Erythromycin biosynthesis in Nat Prod Rep 18, 380 (2001)
Type II PKS (iterative)
- Three proteins (KSα, KSβ, ACP) are repeatedly used for carbon chain elongation.
- Chain length is determined by another protein, CLF.
- In bacteria, products are aromatic (e.g. chiorotetracycline, pradimicin).
- In fungi, products are both non-aromatic and aromatic.
Non-ribosomal peptide synthase (NRPS)
Coupling with PKS and NRPS
- vancomycin ()
- leinamycin (Curr opin chem biol 7:285, 2003)
- pseurotin (chem bio chem 8:1736-1743, 2007)
- curacin (curr opin chem biol 13:216, 2009)
- epothilone
- rapamycin
PKS in Fungi
- both aromatic and non-aromatic compounds are generated by iterative PKS
- methyl branch is transferred from methionine, not methylmalonyl CoA
Ref. Dewick, PM Medicinal Natural Products (2009)
Decoration
deoxysugars
deoxygenation, c-methylation, amination, n-methylation, ketosugar,
Unusual structures
| Phoma | zaragozic acid, phomoidoride | Streptomyces | yatakemycin, leinamycin, saframycin, neocarzinostatin, staurosporin, FR182877 | Other bacteria | PKS-NRPS hybrid type
Curacin A (Lyngbya), Shiphonazole (Herpetosiphon), Jamaicamide A (Lyngbya), Cylindrospermopsin (Cylindrospermopsis) |
|---|
