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Review
. 2010 Sep 3;285(36):27509-15.
doi: 10.1074/jbc.R110.130419. Epub 2010 Jun 3.

Oxytetracycline biosynthesis

Lauren B Pickens  1 , Yi Tang
Affiliations
Review

Oxytetracycline biosynthesis

Lauren B Pickens et al. J Biol Chem. .

Abstract

Oxytetracycline (OTC) is a broad-spectrum antibiotic that acts by inhibiting protein synthesis in bacteria. It is an important member of the bacterial aromatic polyketide family, which is a structurally diverse class of natural products. OTC is synthesized by a type II polyketide synthase that generates the poly-beta-ketone backbone through successive decarboxylative condensation of malonyl-CoA extender units, followed by modifications by cyclases, oxygenases, transferases, and additional tailoring enzymes. Genetic and biochemical studies have illuminated most of the steps involved in the biosynthesis of OTC, which is detailed here as a representative case study in type II polyketide biosynthesis.

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Figures

FIGURE 1.
FIGURE 1.
A, naturally produced tetracyclines; B, semisynthetic second and third generation tetracyclines; C, additional naturally occurring type II polyketides referenced in text.
FIGURE 2.
FIGURE 2.
A, polyketide elongation by iterative Claisen-like condensation; B, two proposed pathways for biosynthesis of the malonamate starter unit by OxyD. MAT, malonyl-CoA:ACP acyltransferase.
FIGURE 3.
FIGURE 3.
Biosynthesis of OTC and reported shunt products.
FIGURE 4.
FIGURE 4.
OTC gene cluster from S. rimosus.
See this image and copyright information in PMC

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