Category:PK

From Metabolomics.JP
Revision as of 12:30, 6 March 2010 by Adm (Talk | contribs)

Jump to: navigation, search

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)

File:1,3,8-Trihydroxyaceto-Naphthalene.Mol
File:1,3-Dihydroxy-N-Methylacridone.Mol
File:3,8-Dihydroxy-1-Methylanthraquinone-2-Carboxylic Acid.Mol
File:4-Hydroxy-2-Quinolone.Mol
File:5,7-Dihydroxy-2-Methylchromone.Mol
File:5-Methylorsellinic Acid.Mol
File:6-Deoxy-Erythronolide B.Mol
File:6-Methoxymellein.Mol
File:6-Methyl Salicylic Acid.Mol
File:Actinorhodin.Mol
File:Adhyperforin.Mol
File:Aflatoxin B1.Mol
File:Aflatoxin B2.Mol
File:Aflatoxin G1.Mol
File:Aflatoxin G2.Mol
File:Aflatoxin M1.Mol
File:Aloe-Emodin.Mol
File:Aloesaponarin II.Mol
File:Alternapyrone.Mol
File:Alternaric Acid.Mol
File:Alternariol.Mol
File:Amphotericin B.Mol
File:Andrimid .Mol
File:Ascomycin.Mol
File:Aslaniol.Mol
File:Aslanipyrone.Mol
File:Asperlactone.Mol
File:Asperlin.Mol
File:Aspyridone A.Mol
File:Aspyridone B.Mol
File:Aspyrone.Mol
File:Asteltoxin.Mol
File:Astepyrone.Mol
File:Atrochrysone.Mol
File:Atrochrysone Carboxylic Acid.Mol
File:Aureothin.Mol
File:Austdiol.Mol
File:Avenaciolide.Mol
File:Averantin.Mol
File:Avermectin B1A.Mol
File:Avermectin B2A.Mol
File:Averufin.Mol
File:Avilamycin.Mol
File:Barnol.Mol
File:Benzophenone.Mol
File:Bikaverin.Mol
File:Botryodiplodin.Mol
File:Brefeldin A.Mol
File:Brevetoxin A.Mol
File:Brevetoxin B.Mol
File:C-1027.Mol
File:Calichemicin Gamma1.Mol
File:Cannabidiol.Mol
File:Cannabigerolic Acid.Mol
File:Cannabinol.Mol
File:Cercosporin.Mol
File:Chlortetracycline.Mol
File:Chrysomycin A.Mol
File:Chrysomycin B.Mol
File:Chrysophanol.Mol
File:Chrysophanol Anthrone.Mol
File:Ciguatoxin I.Mol
File:Citreomontanin.Mol
File:Citreoviridin.Mol
File:Citrinin.Mol
File:Clavatol.Mol
File:Coarctatin.Mol
File:Colletodiol.Mol
File:Compactin.Mol
File:Curvularin.Mol
File:Deoxyherquienone.Mol
File:Deoxyradicin.Mol
File:Dihydroisocoumarin.Mol
File:Diplosporin.Mol
File:Discodermolide.Mol
File:Doramectin.Mol
File:Dothistromin.Mol
File:Doxorubicin.Mol
File:Emodin.Mol
File:Emodin Anthrone.Mol
File:Emodin Dianthrone.Mol
File:Endocrocin.Mol
File:Endocrocin Anthrone.Mol
File:Enniatin B.Mol
File:Enterocin.Mol
File:Epothilone A.Mol
File:Epothilone B.Mol
File:Epothilone C.Mol
File:Epothilone D.Mol
File:Epoxydon.Mol
File:Epsilon-Pyrromycinone.Mol
File:Erythromycin.Mol
File:Flavipin.Mol
File:Fumigatin.Mol
File:Fumonisin B1.Mol
File:Furanomycin.Mol
File:Geldanamycin.Mol
File:Griseofulvin.Mol
File:Griseophenone B.Mol
File:Griseophenone C.Mol
File:Humulone.Mol
File:Hyperforin.Mol
File:Hypericin.Mol
File:Islandicin.Mol
File:Isoepoxydon.Mol
File:Isousnic Acid.Mol
File:Ivermectin.Mol
File:Khellin.Mol
File:Lasalocid.Mol
File:Lecanoric Acid.Mol
File:Leucomycin A1.Mol
File:Ll-D253Alpha.Mol
File:Lovastatin.Mol
File:M-Cresol.Mol
File:Melanin.Mol
File:Mellein.Mol
File:Methylphloracetophenone.Mol
File:Mollisin.Mol
File:Monensin A.Mol
File:Multicolic Acid.Mol
File:Mycolactone.Mol
File:Mycophenolic Acid.Mol
File:Myxalamide.Mol
File:Myxothiazol Z.Mol
File:Niddamycin.Mol
File:Norsolorinic Acid.Mol
File:Nystatin.Mol
File:Ochratoxin A.Mol
File:Ochrephilone.Mol
File:Okadaic Acid.Mol
File:Oleandomycin.Mol
File:Olivetolic Acid.Mol
File:O-Methylasparvenone.Mol
File:Orcinol.Mol
File:Orsellinic Acid.Mol
File:Oxytetracycline.Mol
File:Palitantin.Mol
File:Patulin.Mol
File:Penicillic Acid.Mol
File:Phloracetophenone.Mol
File:Phlorisobutyrophenone.Mol
File:Phlorisovalerophenone.Mol
File:Physcion.Mol
File:Picromycin.Mol
File:Pimaricin.Mol
File:Pretetramide.Mol
File:Protohypericin.Mol
File:Pyochelin.Mol
File:Pyoluteorin.Mol
File:Radicin.Mol
File:Rapamycin.Mol
File:Ravenilin.Mol
File:Rhein.Mol
File:Rifabutin.Mol
File:Rifamycin B.Mol
File:Rifapentine.Mol
File:Rosellisin.Mol
File:Rubrofusarin.Mol
File:Rubropunctatin.Mol
File:Sclerin.Mol
File:Sclerotinin A.Mol
File:Sek4.Mol
File:Sek4B.Mol
File:Selamectin.Mol
File:Sennidin A.Mol
File:Sennidin B.Mol
File:Sennidin C.Mol
File:Sennidin D.Mol
File:Sennosides A.Mol
File:Sennosides B.Mol
File:Sennosides C.Mol
File:Sennosides D.Mol
File:Sepedonin.Mol
File:Siccanin.Mol
File:Silvaticamide.Mol
File:Sma76A.Mol
File:Sma76B.Mol
File:Sma76C.Mol
File:Soraphen A.Mol
File:Spinulosin.Mol
File:Spiramycin I.Mol
File:Sterigmatocystin.Mol
File:Stigmatellin A.Mol
File:Stipitatonic Acid.Mol
File:Sulochrin.Mol
File:Tacrolimus.Mol
File:Tajixanthone.Mol
File:Tennellin.Mol
File:Terrein.Mol
File:Terrequinone A.Mol
File:Tetracenomycin F2.Mol
File:Tetracycline.Mol
File:Tetrahydro Cannabinol.Mol
File:Tetrahydroxynaphthalene.Mol
File:Triacetic Acid Lactone.Mol
File:T-Toxin.Mol
File:Tylactone.Mol
File:Tylosin.Mol
File:Urushiol III.Mol
File:Usnic Acid.Mol
File:Variotin.Mol
File:Versicolorin A.Mol
File:Versicolorin B.Mol
File:Versiconal.Mol
File:Versiconal Acetate.Mol
File:Visnagin.Mol
File:Wa-Naphthopyron.Mol
File:Zaragozic Acids A.Mol
File:Zearalenone.Mol

Subcategories

This category has only the following subcategory.

P

  • [×] PKS‎ (empty)
Retrieved from "http://metabolomics.jp/mediawiki/index.php?title=Category:PK&oldid=114113"
Personal tools
Namespaces

Variants
Actions
Navigation
metabolites
Toolbox