Category:PK

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(Polyketide Synthase (PKS))
(Non-ribosomal peptide synthase (NRPS))
Line 68: Line 68:
 
==Non-ribosomal peptide synthase (NRPS)==
 
==Non-ribosomal peptide synthase (NRPS)==
  
 +
Coupling with PKS and NRPS
  
vancomycin
+
* 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==
 
==PKS in Fungi==

Revision as of 09:23, 14 November 2009

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)

actinomycetes
(bacteria)
fungi
non-aromatic Type I
(non-iterative)
Type II
(iterative)
aromatic Type II
(iterative)
Type II
(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 (e.g. erythromycin, nigericin)

Ref. Erythromycin biosynthesis in Nat Prod Rep 18, 380 (2001)

Type II PKS (iterative)

  • three proteins (KSalpha, KSbeta, ACP) are repeatedly used for carbon chain elongation
  • chain length is determined by another protein, CLF
  • products are aromatic (e.g. chiorotetracycline, pradimicin)

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)

Subcategories

This category has only the following subcategory.

P

  • [×] PKS(empty)
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