Circular logic: nonribosomal peptide-like macrocyclization with a ribosomal peptide catalyst - PubMed (original) (raw)
Circular logic: nonribosomal peptide-like macrocyclization with a ribosomal peptide catalyst
John A McIntosh et al. J Am Chem Soc. 2010.
Abstract
A protease from ribosomal peptide biosynthesis macrocyclizes diverse substrates, including those resembling nonribosomal peptide and hybrid polyketide-peptide products. The proposed mechanism is analogous to thioesterase-catalyzed chemistry, but the substrates are amide bonds rather than thioesters.
Figures
Figure 1. Macrocyclization in ribosomal and nonribosomal synthesis
A) The nonribosomal TycC TE domain circularizes tyrocidines. PCP = peptidyl carrier protein. B) The ribosomally acting PatG protease circularizes patellamides and many other compounds. The proposed catalytic mechanism is indicated here. Tzl = thiazol(ine); MOzl = methyloxazoline.
Figure 2. Products of PatG macrocyclization
A) Representative known natural products cyclized by PatG, out of a total of 39 known natural products in this series. B) Macrocyclization products from this study, showing side-chain circularization (28, 43) and polyketide-like cyclization (41, 42).
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