☆ 4.8 Article

Biocatalytic control of site-selectivity and chain length selectivity in radical amino acid halogenases

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2023)

相关参考文献

注意：仅列出部分参考文献，下载原文获取全部文献信息。

Article Chemistry, Multidisciplinary

Taming the Chlorine Radical: Enforcing Steric Control over Chlorine-Radical-Mediated C-H Activation

Miguel Gonzalez et al.

Summary: The secondary coordination sphere of a metal complex can confine photoeliminated chlorine radicals and provide steric control over their reactivity. This study demonstrates the activity of iron(III) chloride pyridinediimine complexes for selective C(sp(3))-H chlorination and bromination, overriding thermodynamic preference. Transient absorption spectroscopy and photocrystallography confirm the confinement and selectivity arising from the iron secondary coordination sphere.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Empirical Guidelines for the Development of Remote Directing Templates through Quantitative and Experimental Analyses

Nelson Y. S. Lam et al.

Summary: This study summarizes key factors for achieving high selectivity at defined aryl positions by analyzing 119 structurally unique remote DTs, which are experimentally corroborated through the development of new aliphatic meta and para-selective DTs for electronically unbiased arenes. These empirical rules, summarizing key distance and geometric factors, are expected to be useful tools for the future development of site-selective arene C-H activation and other reactions relying on covalent/noncovalent DT-mediated remote regioselection.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

添加到收藏夹

Article Biochemistry & Molecular Biology

Reaction pathway engineering converts a radical hydroxylase into a halogenase

Monica E. Neugebauer et al.

Summary: Researchers have developed a strategy to expand enzymatic halogenation by engineering a reaction pathway rather than substrate selectivity. They discovered active halogenases from a DNA shuffle library and engineered a hydroxylase to perform halogenation with comparable activity and higher selectivity than the wild-type halogenase, showcasing the potential of harnessing hydroxylases for biocatalytic halogenation.

NATURE CHEMICAL BIOLOGY (2022)

添加到收藏夹

Article Multidisciplinary Sciences

Algorithm-aided engineering of aliphatic halogenase WelO5*for the asymmetric late-stage functionalization of soraphens

Johannes Buechler et al.

Summary: The authors used machine learning to engineer WelO5* halogenase variants, enabling the regioselective chlorination of unactivated carbon-hydrogen bonds. Late-stage functionalization of natural products offers a promising route for creating novel entities.

NATURE COMMUNICATIONS (2022)

添加到收藏夹

Article Multidisciplinary Sciences

Design principles for site-selective hydroxylation by a Rieske oxygenase

Jianxin Liu et al.

Summary: In this study, the crystal structures of two Rieske oxygenases, SxtT and GxtA, were determined with their native substrates. The authors also identified key amino acid residues that determine the substrate specificity and site selectivity of these enzymes. These findings provide valuable insights for the engineering of Rieske oxygenases.

NATURE COMMUNICATIONS (2022)

添加到收藏夹

Article Multidisciplinary Sciences

Biocatalytic oxidative cross-coupling reactions for biaryl bond formation

Lara E. Zetzsche et al.

Summary: This study demonstrates the use of cytochrome P450 enzymes for biocatalytic cross-coupling reactions, enabling the formation of sterically hindered biaryl bonds through oxidative C-C bond formation. By engineering the substrate and atroposelectivity of the P450 enzyme, a highly efficient and selective process has been developed.

NATURE (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

A Chiral-Pool-Based Strategy to Access trans-syn-Fused Drimane Meroterpenoids: Chemoenzymatic Total Syntheses of Polysin, N-Acetyl-polyveoline and the Chrodrimanins

Fuzhuo Li et al.

Summary: In this study, the first total syntheses of four trans-syn-fused drimane meroterpenoids were reported, achieved in 7-18 steps from sclareolide. The trans-syn-fused drimane unit was accessed through efficient acid-mediated epimerization of sclareolide, and subsequent enzymatic C-H oxidation and contemporary annulation methodologies were applied to rapidly generate structural complexity for concise access to these natural products.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

A directive Ni catalyst overrides conventional site selectivity in pyridine C-H alkenylation

Tao Zhang et al.

Summary: This study reports a bifunctional N-heterocyclic carbene-ligated Ni-Al catalyst that can smoothly carry out the C3-H alkenylation of pyridines. This method provides a series of C3-alkenylated pyridines in yields ranging from 43-99% and with up to 98:2 C3 selectivity. It is effective for late-stage C3 alkenylation of diverse complex pyridine motifs in bioactive molecules, allowing various pyridine and heteroarene substrates to be used as the limiting reagent.

NATURE CHEMISTRY (2021)

添加到收藏夹

Article Chemistry, Organic

Regiodivergent biocatalytic hydroxylation of L-Glutamine facilitated by characterization of Non-Heme dioxygenases from Non-Ribosomal peptide biosyntheses

Hans Renata et al.

Summary: We reported the functional characterization of two iron- and alpha-ketoglutarate-dependent dioxygenases capable of hydroxylating free-standing glutamine at its C3 and C4 position respectively. In particular, the C4 hydroxylase, Q4Ox, catalyzed the reaction with approximately 4300 total turnover numbers, facilitating synthesis of a solid-phase compatible building block and stereochemical elucidation at the C4 position of the hydroxylated product. This work will enable the development of novel synthetic strategies to prepare useful glutamine derivatives and stimulate further discoveries of new amino acid hydroxylases with distinct substrate specificities.

TETRAHEDRON (2021)

添加到收藏夹

Article Chemistry, Physical

Programmable late-stage C-H bond functionalization enabled by integration of enzymes with chemocatalysis

Elliott J. Craven et al.

Summary: New chemo- and biocatalytic methodologies are crucial for the sustainable synthesis of essential molecules in the future. Transition metal catalysis allows for late-stage C-H functionalization of complex molecular scaffolds, while enzymes provide exquisite regioselectivity but access to fewer functionalities compared to more divergent chemocatalysis.

NATURE CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Physical

Spectroscopically Guided Simulations Reveal Distinct Strategies for Positioning Substrates to Achieve Selectivity in Nonheme Fe(II)/α-Ketoglutarate-Dependent Halogenases

Rimsha Mehmood et al.

Summary: Researchers investigate substrate/active-site dynamics of nonheme iron halogenases like BesD and WelO5 using experimental and computational methods, revealing the importance of active-site configurational isomerization for selective halogenation in WelO5. They also find distinct patterns of substrate-protein interactions for these enzymes, and discuss how optimal substrate/active-site geometry plays a crucial role in facilitating chemoselectivity in halogenases. Their work demonstrates different substrate-dependent strategies used to promote selectivity in halogenases.

ACS CATALYSIS (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

State-of-the-Art Biocatalysis

Joshua B. Pyser et al.

Summary: Enzyme-mediated reactions have moved beyond ancient food production to laboratory synthesis of complex molecules, driven by advancements in sequencing, DNA synthesis, bioinformatics, protein engineering, and interdisciplinary research. Biocatalysis has become essential in both academic and industrial settings, offering precise selectivity for accessing target molecules. The future of biocatalysis lies in integrating well-characterized enzymes into mainstream synthetic chemistry to enhance efficiency and throughput in synthesizing increasingly complex molecules.

ACS CENTRAL SCIENCE (2021)

添加到收藏夹

Article Chemistry, Multidisciplinary

An Fe2+- and α-Ketoglutarate-Dependent Halogenase Acts on Nucleotide Substrates

Chunhua Zhao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

添加到收藏夹

Article Multidisciplinary Sciences

Diverse functionalization of strong alkyl C-H bonds by undirected borylation

Raphael Oeschger et al.

SCIENCE (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Achieving Site-Selectivity for C-H Activation Processes Based on Distance and Geometry: A Carpenter's Approach

Guangrong Meng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Development and Mechanistic Interrogation of Interrupted Chain-Walking in the Enantioselective Relay Heck Reaction

Sean P. Ross et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

添加到收藏夹

Article Multidisciplinary Sciences

Structural basis for divergent C-H hydroxylation selectivity in two Rieske oxygenases

April L. Lukowski et al.

NATURE COMMUNICATIONS (2020)

添加到收藏夹

Article Multidisciplinary Sciences

An iron (II) dependent oxygenase performs the last missing step of plant lysine catabolism

Mitchell G. Thompson et al.

NATURE COMMUNICATIONS (2020)

添加到收藏夹

Article Multidisciplinary Sciences

Divergent synthesis of complex diterpenes through a hybrid oxidative approach

Xiao Zhang et al.

SCIENCE (2020)

添加到收藏夹

Article Biochemistry & Molecular Biology

Concise Chemoenzymatic Total Synthesis and Identification of Cellular Targets of Cepafungin I

Alexander Amatuni et al.

CELL CHEMICAL BIOLOGY (2020)

添加到收藏夹

Article Multidisciplinary Sciences

Discovery of a pathway for terminal-alkyne amino acid biosynthesis

J. A. Marchand et al.

NATURE (2019)

添加到收藏夹

Review Biochemistry & Molecular Biology

Selective C-H bond functionalization with engineered heme proteins: new tools to generate complexity

Ruijie K. Zhang et al.

CURRENT OPINION IN CHEMICAL BIOLOGY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantiodivergent α-Amino C-H Fluoroalkylation Catalyzed by Engineered Cytochrome P450s

Juner Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

添加到收藏夹

Article Biochemistry & Molecular Biology

A family of radical halogenases for the engineering of amino-acid-based products

Monica E. Neugebauer et al.

NATURE CHEMICAL BIOLOGY (2019)

添加到收藏夹

Article Multidisciplinary Sciences

Design of an invitro biocatalytic cascade for the manufacture of islatravir

Mark A. Huffman et al.

SCIENCE (2019)

添加到收藏夹

Review Biochemistry & Molecular Biology

Halogenases: powerful tools for biocatalysis (mechanisms applications and scope)

Danai S. Gkotsi et al.

CURRENT OPINION IN CHEMICAL BIOLOGY (2018)

添加到收藏夹

Article Multidisciplinary Sciences

Structural Studies based on two Lysine Dioxygenases with Distinct Regioselectivity Brings Insights Into Enzyme Specificity within the Clavaminate Synthase-Like Family

Karine Bastard et al.

SCIENTIFIC REPORTS (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

Extending the application of biocatalysis to meet the challenges of drug development

Paul N. Devine et al.

NATURE REVIEWS CHEMISTRY (2018)

添加到收藏夹

Article Chemistry, Physical

Opportunities and challenges for combining chemo- and biocatalysis

Florian Rudroff et al.

NATURE CATALYSIS (2018)

添加到收藏夹

Review Chemistry, Multidisciplinary

Palladium-Catalyzed Transformations of Alkyl C-H Bonds

Jian He et al.

CHEMICAL REVIEWS (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Frontier Molecular Orbital Contributions to Chlorination versus Hydroxylation Selectivity in the Non-Heme Iron Halogenase SyrB2

Martin Srnec et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

添加到收藏夹

Article Multidisciplinary Sciences

Genetically programmed chiral organoborane synthesis

S. B. Jennifer Kan et al.

NATURE (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective, intermolecular benzylic C-H amination catalysed by an engineered iron-haem enzyme

Christopher K. Prier et al.

NATURE CHEMISTRY (2017)

添加到收藏夹

Review Chemistry, Multidisciplinary

Enzymatic Halogenation and Dehalogenation Reactions: Pervasive and Mechanistically Diverse

Vinayak Agarwal et al.

CHEMICAL REVIEWS (2017)

添加到收藏夹

Article Chemistry, Multidisciplinary

Discovery of a Promiscuous Non-Heme Iron Halogenase in Ambiguine Alkaloid Biogenesis: Implication for an Evolvable Enzyme Family for Late-Stage Halogenation of Aliphatic Carbons in Small Molecules

Matthew L. Hillwig et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

添加到收藏夹

Article Chemistry, Medicinal

Unusual Amino Acids in Medicinal Chemistry

Mark A. T. Blaskovich

JOURNAL OF MEDICINAL CHEMISTRY (2016)

添加到收藏夹

Article Biochemistry & Molecular Biology

Structural basis for halogenation by iron- and 2-oxo-glutarate-dependent enzyme WelO5

Andrew J. Mitchell et al.

Nature Chemical Biology (2016)

添加到收藏夹

Article Multidisciplinary Sciences

Directed evolution of cytochrome c for carbon-silicon bond formation: Bringing silicon to life

S. B. Jennifer Kan et al.

SCIENCE (2016)

添加到收藏夹

Article Chemistry, Physical

Late-Stage Diversification of Biologically Active Molecules via Chemoenzymatic C-H Functionalization

Landon J. Durak et al.

ACS CATALYSIS (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

CalFluors: A Universal Motif for Fluorogenic Azide Probes across the Visible Spectrum

Peyton Shieh et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Experimental Correlation of Substrate Position with Reaction Outcome in the Aliphatic Halogenase, SyrB2

Ryan J. Martinie et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

添加到收藏夹

Article Biochemistry & Molecular Biology

More than just a Halogenase: Modification of Fatty Acyl Moieties by a Trifunctional Metal Enzyme

Sarah M. Pratter et al.

CHEMBIOCHEM (2014)

添加到收藏夹

Article Biochemistry & Molecular Biology

A new family of iron-dependent halogenases acts on freestanding substrates

Matthew L. Hillwig et al.

NATURE CHEMICAL BIOLOGY (2014)

添加到收藏夹

Article Biochemistry & Molecular Biology

Direct nitration and azidation of aliphatic carbons by an iron-dependent halogenase

Megan L. Matthews et al.

NATURE CHEMICAL BIOLOGY (2014)

添加到收藏夹

Article Multidisciplinary Sciences

Elucidation of the Fe(IV)=O intermediate in the catalytic cycle of the halogenase SyrB2

Shaun D. Wong et al.

NATURE (2013)

添加到收藏夹

Article Biochemistry & Molecular Biology

ECMDB: The E-coli Metabolome Database

An Chi Guo et al.

NUCLEIC ACIDS RESEARCH (2013)

添加到收藏夹

Review Chemistry, Multidisciplinary

Expanding the organic toolbox: a guide to integrating biocatalysis in synthesis

Christopher M. Clouthier et al.

CHEMICAL SOCIETY REVIEWS (2012)

添加到收藏夹

Article Biophysics

Structural insight into the substrate- and dioxygen-binding manner in the catalytic cycle of Rieske nonheme iron oxygenase system, carbazole 1,9a-dioxygenase

Yuji Ashikawa et al.

BMC STRUCTURAL BIOLOGY (2012)

添加到收藏夹

Article Biochemistry & Molecular Biology

Biosynthetic Chlorination of the Piperazate Residue in Kutzneride Biosynthesis by KthP

Wei Jiang et al.

BIOCHEMISTRY (2011)

添加到收藏夹

Review Chemistry, Multidisciplinary

Palladium-Catalyzed Ligand-Directed C-H Functionalization Reactions

Thomas W. Lyons et al.

CHEMICAL REVIEWS (2010)

添加到收藏夹

Article Multidisciplinary Sciences

Conformational switch triggered by α-ketoglutarate in a halogenase of curacin A biosynthesis

Dheeraj Khare et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2010)

添加到收藏夹

Article Multidisciplinary Sciences

Biocatalytic Asymmetric Synthesis of Chiral Amines from Ketones Applied to Sitagliptin Manufacture

Christopher K. Savile et al.

SCIENCE (2010)

添加到收藏夹

Article Multidisciplinary Sciences

Substrate positioning controls the partition between halogenation and hydroxylation in the aliphatic halogenase, SyrB2

Megan L. Matthews et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2009)

添加到收藏夹

Article Chemistry, Multidisciplinary

Biosynthesis of (-)-(1S,2R)-Allocoronamic Acyl Thioester by an FeII-Dependent Halogenase and a Cyclopropane-Forming Flavoprotein

Christopher S. Neumann et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

添加到收藏夹

Article Biochemistry & Molecular Biology

Electron transfer complex formation between oxygenase and ferredoxin components in Rieske nonheme iron oxygenase system

Yuji Ashikawa et al.

STRUCTURE (2006)

添加到收藏夹

Article Biochemistry & Molecular Biology

Enzymatic generation of the antimetabolite γ,γ-dichloroaminobutyrate by NRPS and mononuclear iron halogenase action in a streptomycete

Masashi Ueki et al.

CHEMISTRY & BIOLOGY (2006)

添加到收藏夹

Article Plant Sciences

Characterization of the initial enzymatic steps of barbamide biosynthesis

Patricia M. Flatt et al.

JOURNAL OF NATURAL PRODUCTS (2006)

添加到收藏夹

Article Biochemical Research Methods

An assay for Fe(II)/2-oxoglutarate-dependent dioxygenases by enzyme-coupled detection of succinate formation

LS Luo et al.

ANALYTICAL BIOCHEMISTRY (2006)

添加到收藏夹

Article Chemistry, Multidisciplinary

Halogenation of unactivated carbon centers in natural product biosynthesis: Trichlorination of leucine during barbamide biosynthesis

DP Galonic et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

添加到收藏夹

Article Multidisciplinary Sciences

Crystal structure of the non-haem iron halogenase SyrB2 in syringomycin biosynthesis

LC Blasiak et al.

NATURE (2006)

添加到收藏夹

Article Multidisciplinary Sciences

Cryptic chlorination by a non-haem iron enzyme during cyclopropyl amino acid biosynthesis

FH Vaillancourt et al.

NATURE (2005)

添加到收藏夹

Article Biochemistry & Molecular Biology

Structure of proline 3-hydroxylase - Evolution of the family of 2-oxoglutarate dependent oxygenases

IJ Clifton et al.

EUROPEAN JOURNAL OF BIOCHEMISTRY (2001)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.