Streamlined Chemoenzymatic Synthesis of Cyclic Peptides by Non-ribosomal Peptide Cyclases

Kobayashi, Masakazu; Fujita, Kazuo; Matsuda, Kazuo; Wakimoto, Toshiyuki

doi:10.1021/jacs.2c11082

Cited by 27 publications

(19 citation statements)

References 27 publications

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“…Increasing recognition of the importance of macrocyclic peptides has driven the use of thioesterases (TEs) to enable protecting group free macrocyclization via amide bond formation . The application of this enzyme class in vitro was historically limited by the requirement for a C-terminal N -acetylcysteamine (SNAC) peptide thioester to enable TE biocatalysis following solid-phase peptide synthesis .…”

Section: Functional Group Manipulationmentioning

confidence: 99%

“…Increasing recognition of the importance of macrocyclic peptides 49 has driven the use of thioesterases (TEs) to enable protecting group free macrocyclization via amide bond formation. 50 The application of this enzyme class in vitro was historically limited by the requirement for a C-terminal Nacetylcysteamine (SNAC) peptide thioester to enable TE biocatalysis following solid-phase peptide synthesis. 51 This penultimate coupling step introduces an additional expense by requiring coupling with N-acetylcysteamine, leads to epimerization of the α position, and complicates HPLC purification.…”

Section: Carboxylic Acid Derivative Hydrolysis and Formationmentioning

confidence: 99%

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Non-Native Site-Selective Enzyme Catalysis

Mondal,

Snodgrass,

Gomez

et al. 2023

Chem. Rev.

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The ability to site-selectively modify equivalent functional groups in a molecule has the potential to streamline syntheses and increase product yields by lowering step counts. Enzymes catalyze site-selective transformations throughout primary and secondary metabolism, but leveraging this capability for non-native substrates and reactions requires a detailed understanding of the potential and limitations of enzyme catalysis and how these bounds can be extended by protein engineering. In this review, we discuss representative examples of site-selective enzyme catalysis involving functional group manipulation and C–H bond functionalization. We include illustrative examples of native catalysis, but our focus is on cases involving non-native substrates and reactions often using engineered enzymes. We then discuss the use of these enzymes for chemoenzymatic transformations and target-oriented synthesis and conclude with a survey of tools and techniques that could expand the scope of non-native site-selective enzyme catalysis.

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Section: Functional Group Manipulationmentioning

confidence: 99%

Section: Carboxylic Acid Derivative Hydrolysis and Formationmentioning

confidence: 99%

Non-Native Site-Selective Enzyme Catalysis

Mondal,

Snodgrass,

Gomez

et al. 2023

Chem. Rev.

View full text Add to dashboard Cite

show abstract

“…Increasing recognition of the importance of macrocyclic peptides 48 has driven the use of thioesterases (TEs) to enable protecting group free macrocylization via amide bond formation. 49 The application of this enzyme class in vitro was historically limited by the requirement for a Cterminal N-acetylcysteamine (SNAC) peptide thioester to enable TE biocatalysis following solid phase peptide synthesis. 50 This penultimate coupling step introduces an additional expense by requiring coupling with N-acetylcysteamine, leads to epimerization of the α-position, and complicates HPLC purification.…”

Section: Carboxylic Amide Formationmentioning

confidence: 99%

Non-Native Site-Selective Enzyme Catalysis

Mondal

Snodgrass

Gomez

et al. 2023

Preprint

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The ability to a site-selectively modify equivalent functional groups in a molecule has the potential to streamline syntheses and increase product yields by lowering step counts. Enzymes catalyze site-selective transformations throughout primary and secondary metabolism, but leveraging this capability for non-native substrates and reactions requires a detailed understanding of the potential and limitations of enzyme catalysis and how these bounds can be extended by protein engineering. In this review, we discuss representative examples of site-selective enzyme catalysis involving functional group manipulation and C-H bond functionalization. We include illustrative examples of native catalysis, but our focus is on cases involving non-native substrates and reactions often using engineered enzymes. We then discuss the use of these enzymes for chemoenzymatic transformations and target-oriented synthesis and conclude with a survey of tools and techniques that could expand the scope of non-native site-selective enzyme catalysis.

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“…This model introduces a novel strategy to develop cyclic peptide-based self-assembly peptide systems that may serve as supramolecular materials for different applications as immunosuppressants, antibiotics, antivirals, or anticancer drugs. [57][58][59] However, its poor solubility in water prevented the formation of stand-alone hydrogels with mechanical properties suited for biotechnology applications, thus suggesting that some optimization still had to be done.…”

Section: Molecular Dynamic Simulationsmentioning

confidence: 99%