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1 article(s) from Weissman, Kira J

Polyketide stereocontrol: a study in chemical biology

Kira J. Weissman

Beilstein J. Org. Chem. 2017, 13, 348–371, doi:10.3762/bjoc.13.39

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Graphical Abstract

Figure 1: Structures of clinically-relevant polyketides: erythromycin A (1), azithromycin (2), clarithromycin...

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Figure 2: Schematic of erythromycin A (1) bound to 23S ribosomal RNA of the 50S subunit of the Deinococcus ra...

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Figure 3: Schematic of the biosynthetic pathway leading to erythromycin A (1) in the bacterium Saccharopolysp...

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Figure 4: Schematic of the virginiamycin PKS from Streptomyces virginiae, a member of the trans-AT PKS family ...

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Figure 5: Determination of the stereochemistry of extender unit selection by the AT domains of modular PKS. a...

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Figure 6: Creation by genetic engineering of the DEBS 1-TE model system. The region of the eryAIII gene encod...

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Figure 7: Model for substrate selection by AT domains. a) Sequence motifs in malonyl- and methylmalonyl-CoA-s...

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Figure 8: Proposed mechanism for KS-catalyzed chain extension, based on extrapolation from studies on homolog...

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Figure 9: Experiment in vitro to determine the stereochemistry of condensation in modular PKS [46]. Use of specif...

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Figure 10: Genetic engineering experiments which suggested a role for the KS domain in epimerization. a) A dik...

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Figure 11: Models for control of the stereochemistry of reduction by KR domains. The two directions of ketored...

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Figure 12: Assays in vitro to evaluate the stereospecificity of recombinant KR domains. A series of KR domains...

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Figure 13: Assays in vitro which provided the first direct evidence that KR domains act as epimerases [77]. Biosyn...

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Figure 14: Assays in vitro to demonstrate directly the epimerase activity of PKS KR domains. a) Equilibrium ex...

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Figure 15: Model for DH-catalyzed generation of trans and cis double bonds by syn elimination from substrates ...

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Figure 16: Stereospecificity of dehydration by Rif DH₁₀ [94]. a) The four possible diastereomeric diketide-ACP sub...

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Figure 17: Stereocontrol by PKS ER domains. Sequence motifs correlated with the final stereochemistry of the C...

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Figure 18: a) PKS engineered to test the role of the ER stereospecificity residues [115]. TKS-ERY4 was created by r...

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Review

Published 24 Feb 2017

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