Category:PK
(→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) |
---|