Category:PK

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Polyketide (ポリケチド)


Contents

Class Overview

Polyketides are synthesized through the polymerization of acetyl units (β-ketomethylene chain).


Table 1. Polyketide Classification
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
griseofulvin, rubrofusarin, emodin, alizarin, pachybasin, xanthone, versicolorin A, aflatoxin B1, sterigmatocystin, tajixanthone

PK9: Nine C2 Units

Tetracyclines
terramycin, aureomycin, daunomycin

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)

1,3,8-Trihydroxyaceto-Naphthalene 1,3,8-Trihydroxyaceto-Naphthalene.Mol.png
1,3-Dihydroxy-N-Methylacridone 1,3-Dihydroxy-N-Methylacridone.Mol.png
3,8-Dihydroxy-1-Methylanthraquinone-2-Carboxylic_Acid 3,8-Dihydroxy-1-Methylanthraquinone-2-Carboxylic Acid.Mol.png
4-Hydroxy-2-Quinolone 4-Hydroxy-2-Quinolone.Mol.png
5,7-Dihydroxy-2-Methylchromone 5,7-Dihydroxy-2-Methylchromone.Mol.png
5-Methylorsellinic_Acid 5-Methylorsellinic Acid.Mol.png
6-Deoxy-Erythronolide_B 6-Deoxy-Erythronolide B.Mol.png
6-Methoxymellein 6-Methoxymellein.Mol.png
6-Methyl_Salicylic_Acid 6-Methyl Salicylic Acid.Mol.png
Actinorhodin Actinorhodin.Mol.png
Adhyperforin Adhyperforin.Mol.png
Aflatoxin_B1 Aflatoxin B1.Mol.png
Aflatoxin_B2 Aflatoxin B2.Mol.png
Aflatoxin_G1 Aflatoxin G1.Mol.png
Aflatoxin_G2 Aflatoxin G2.Mol.png
Aflatoxin_M1 Aflatoxin M1.Mol.png
Aloe-Emodin Aloe-Emodin.Mol.png
Aloesaponarin_II Aloesaponarin II.Mol.png
Alternapyrone Alternapyrone.Mol.png
Alternaric_Acid Alternaric Acid.Mol.png
Alternariol Alternariol.Mol.png
Amphotericin_B Amphotericin B.Mol.png
Andrimid_ Andrimid .Mol.png
Ascomycin Ascomycin.Mol.png
Aslaniol Aslaniol.Mol.png
Aslanipyrone Aslanipyrone.Mol.png
Asperlactone Asperlactone.Mol.png
Asperlin Asperlin.Mol.png
Aspyridone_A Aspyridone A.Mol.png
Aspyridone_B Aspyridone B.Mol.png
Aspyrone Aspyrone.Mol.png
Asteltoxin Asteltoxin.Mol.png
Astepyrone Astepyrone.Mol.png
Atrochrysone Atrochrysone.Mol.png
Atrochrysone_Carboxylic_Acid Atrochrysone Carboxylic Acid.Mol.png
Aureothin Aureothin.Mol.png
Austdiol Austdiol.Mol.png
Avenaciolide Avenaciolide.Mol.png
Averantin Averantin.Mol.png
Avermectin_B1A Avermectin B1A.Mol.png
Avermectin_B2A Avermectin B2A.Mol.png
Averufin Averufin.Mol.png
Avilamycin Avilamycin.Mol.png
Barnol Barnol.Mol.png
Benzophenone Benzophenone.Mol.png
Bikaverin Bikaverin.Mol.png
Botryodiplodin Botryodiplodin.Mol.png
Brefeldin_A Brefeldin A.Mol.png
Brevetoxin_A Brevetoxin A.Mol.png
Brevetoxin_B Brevetoxin B.Mol.png
C-1027 C-1027.Mol.png
Calichemicin_Gamma1 Calichemicin Gamma1.Mol.png
Cannabidiol Cannabidiol.Mol.png
Cannabigerolic_Acid Cannabigerolic Acid.Mol.png
Cannabinol Cannabinol.Mol.png
Cercosporin Cercosporin.Mol.png
Chlortetracycline Chlortetracycline.Mol.png
Chrysomycin_A Chrysomycin A.Mol.png
Chrysomycin_B Chrysomycin B.Mol.png
Chrysophanol Chrysophanol.Mol.png
Chrysophanol_Anthrone Chrysophanol Anthrone.Mol.png
Ciguatoxin_I Ciguatoxin I.Mol.png
Citreomontanin Citreomontanin.Mol.png
Citreoviridin Citreoviridin.Mol.png
Citrinin Citrinin.Mol.png
Clavatol Clavatol.Mol.png
Coarctatin Coarctatin.Mol.png
Colletodiol Colletodiol.Mol.png
Compactin Compactin.Mol.png
Curvularin Curvularin.Mol.png
Deoxyherquienone Deoxyherquienone.Mol.png
Deoxyradicin Deoxyradicin.Mol.png
Dihydroisocoumarin Dihydroisocoumarin.Mol.png
Diplosporin Diplosporin.Mol.png
Discodermolide Discodermolide.Mol.png
Doramectin Doramectin.Mol.png
Dothistromin Dothistromin.Mol.png
Doxorubicin Doxorubicin.Mol.png
Emodin Emodin.Mol.png
Emodin_Anthrone Emodin Anthrone.Mol.png
Emodin_Dianthrone Emodin Dianthrone.Mol.png
Endocrocin Endocrocin.Mol.png
Endocrocin_Anthrone Endocrocin Anthrone.Mol.png
Enniatin_B Enniatin B.Mol.png
Enterocin Enterocin.Mol.png
Epothilone_A Epothilone A.Mol.png
Epothilone_B Epothilone B.Mol.png
Epothilone_C Epothilone C.Mol.png
Epothilone_D Epothilone D.Mol.png
Epoxydon Epoxydon.Mol.png
Epsilon-Pyrromycinone Epsilon-Pyrromycinone.Mol.png
Erythromycin Erythromycin.Mol.png
Flavipin Flavipin.Mol.png
Fumigatin Fumigatin.Mol.png
Fumonisin_B1 Fumonisin B1.Mol.png
Furanomycin Furanomycin.Mol.png
Geldanamycin Geldanamycin.Mol.png
Griseofulvin Griseofulvin.Mol.png
Griseophenone_B Griseophenone B.Mol.png
Griseophenone_C Griseophenone C.Mol.png
Humulone Humulone.Mol.png
Hyperforin Hyperforin.Mol.png
Hypericin Hypericin.Mol.png
Islandicin Islandicin.Mol.png
Isoepoxydon Isoepoxydon.Mol.png
Isousnic_Acid Isousnic Acid.Mol.png
Ivermectin Ivermectin.Mol.png
Khellin Khellin.Mol.png
Lasalocid Lasalocid.Mol.png
Lecanoric_Acid Lecanoric Acid.Mol.png
Leucomycin_A1 Leucomycin A1.Mol.png
Ll-D253Alpha Ll-D253Alpha.Mol.png
Lovastatin Lovastatin.Mol.png
M-Cresol M-Cresol.Mol.png
Melanin Melanin.Mol.png
Mellein Mellein.Mol.png
Methylphloracetophenone Methylphloracetophenone.Mol.png
Mollisin Mollisin.Mol.png
Monensin_A Monensin A.Mol.png
Multicolic_Acid Multicolic Acid.Mol.png
Mycolactone Mycolactone.Mol.png
Mycophenolic_Acid Mycophenolic Acid.Mol.png
Myxalamide Myxalamide.Mol.png
Myxothiazol_Z Myxothiazol Z.Mol.png
Niddamycin Niddamycin.Mol.png
Norsolorinic_Acid Norsolorinic Acid.Mol.png
Nystatin Nystatin.Mol.png
Ochratoxin_A Ochratoxin A.Mol.png
Ochrephilone Ochrephilone.Mol.png
Okadaic_Acid Okadaic Acid.Mol.png
Oleandomycin Oleandomycin.Mol.png
Olivetolic_Acid Olivetolic Acid.Mol.png
O-Methylasparvenone O-Methylasparvenone.Mol.png
Orcinol Orcinol.Mol.png
Orsellinic_Acid Orsellinic Acid.Mol.png
Oxytetracycline Oxytetracycline.Mol.png
Palitantin Palitantin.Mol.png
Patulin Patulin.Mol.png
Penicillic_Acid Penicillic Acid.Mol.png
Phloracetophenone Phloracetophenone.Mol.png
Phlorisobutyrophenone Phlorisobutyrophenone.Mol.png
Phlorisovalerophenone Phlorisovalerophenone.Mol.png
Physcion Physcion.Mol.png
Picromycin Picromycin.Mol.png
Pimaricin Pimaricin.Mol.png
Pretetramide Pretetramide.Mol.png
Protohypericin Protohypericin.Mol.png
Pyochelin Pyochelin.Mol.png
Pyoluteorin Pyoluteorin.Mol.png
Radicin Radicin.Mol.png
Rapamycin Rapamycin.Mol.png
Ravenilin Ravenilin.Mol.png
Rhein Rhein.Mol.png
Rifabutin Rifabutin.Mol.png
Rifamycin_B Rifamycin B.Mol.png
Rifapentine Rifapentine.Mol.png
Rosellisin Rosellisin.Mol.png
Rubrofusarin Rubrofusarin.Mol.png
Rubropunctatin Rubropunctatin.Mol.png
Sclerin Sclerin.Mol.png
Sclerotinin_A Sclerotinin A.Mol.png
Sek4 Sek4.Mol.png
Sek4B Sek4B.Mol.png
Selamectin Selamectin.Mol.png
Sennidin_A Sennidin A.Mol.png
Sennidin_B Sennidin B.Mol.png
Sennidin_C Sennidin C.Mol.png
Sennidin_D Sennidin D.Mol.png
Sennosides_A Sennosides A.Mol.png
Sennosides_B Sennosides B.Mol.png
Sennosides_C Sennosides C.Mol.png
Sennosides_D Sennosides D.Mol.png
Sepedonin Sepedonin.Mol.png
Siccanin Siccanin.Mol.png
Silvaticamide Silvaticamide.Mol.png
Sma76A Sma76A.Mol.png
Sma76B Sma76B.Mol.png
Sma76C Sma76C.Mol.png
Soraphen_A Soraphen A.Mol.png
Spinulosin Spinulosin.Mol.png
Spiramycin_I Spiramycin I.Mol.png
Sterigmatocystin Sterigmatocystin.Mol.png
Stigmatellin_A Stigmatellin A.Mol.png
Stipitatonic_Acid Stipitatonic Acid.Mol.png
Sulochrin Sulochrin.Mol.png
Tacrolimus Tacrolimus.Mol.png
Tajixanthone Tajixanthone.Mol.png
Tennellin Tennellin.Mol.png
Terrein Terrein.Mol.png
Terrequinone_A Terrequinone A.Mol.png
Tetracenomycin_F2 Tetracenomycin F2.Mol.png
Tetracycline Tetracycline.Mol.png
Tetrahydro_Cannabinol Tetrahydro Cannabinol.Mol.png
Tetrahydroxynaphthalene Tetrahydroxynaphthalene.Mol.png
Triacetic_Acid_Lactone Triacetic Acid Lactone.Mol.png
T-Toxin T-Toxin.Mol.png
Tylactone Tylactone.Mol.png
Tylosin Tylosin.Mol.png
Urushiol_III Urushiol III.Mol.png
Usnic_Acid Usnic Acid.Mol.png
Variotin Variotin.Mol.png
Versicolorin_A Versicolorin A.Mol.png
Versicolorin_B Versicolorin B.Mol.png
Versiconal Versiconal.Mol.png
Versiconal_Acetate Versiconal Acetate.Mol.png
Visnagin Visnagin.Mol.png
Wa-Naphthopyron Wa-Naphthopyron.Mol.png
Zaragozic_Acids_A Zaragozic Acids A.Mol.png
Zearalenone Zearalenone.Mol.png

Subcategories

This category has only the following subcategory.

P

  • [×] PKS‎ (empty)
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