4.8 Article

Discovery and Engineering of the L-Threonine Aldolase from Neptunomonas marine for the Efficient Synthesis of ß-Hydroxy-α-amino Acids via C-C Formation

Related references

Note: Only part of the references are listed.
Article Chemistry, Multidisciplinary

Mutability-Landscape-Guided Engineering of l-Threonine Aldolase Revealing the Prelog Rule in Mediating Diastereoselectivity of C-C Bond Formation

Wenlong Zheng et al.

Summary: In this study, the diastereoselectivity of L-threonine aldolase was tuned using mutagenesis and iterative saturation mutation strategies. The molecular dynamics simulations and coevolution analysis provided insights into the diastereoselectivity regulation mechanism. This research is valuable for expanding the applications of L-threonine aldolase and guiding the engineering of other C-C bond-forming enzymes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Article Biochemistry & Molecular Biology

Scalable and Selective β-Hydroxy-α-Amino Acid Synthesis Catalyzed by Promiscuous l-Threonine Transaldolase ObiH

Tyler J. Doyon et al.

Summary: Enzymes from secondary metabolic pathways show potential for the selective synthesis of bioactive molecules, but their practical application depends on the development of efficient systems. ObiH, an l-threonine transaldolase, demonstrated the ability to selectively synthesize diverse non-standard amino acids on a scalable whole cell platform. Results showed high initial selectivity of the catalyst and a decrease in diastereomeric ratio of products at high conversion.

CHEMBIOCHEM (2022)

Article Chemistry, Physical

Computational Studies Devoted to the Catalytic Mechanism of Threonine Aldolase, a Critical Enzyme in the Pharmaceutical Industry to Synthesize β-Hydroxy-α-amino Acids

Juliana F. Rocha et al.

Summary: The catalytic mechanism of threonine aldolase was studied in detail using computational methods, revealing a three-step process with the covalent bond cleavage as the rate-limiting step. These findings are valuable for optimizing the synthesis of beta-hydroxy-alpha-amino acids, which are important building blocks in various commercial drugs.

ACS CATALYSIS (2022)

Article Chemistry, Physical

An Effective Chemo-Enzymatic method with An Evolved L-Threonine Aldolase for Preparing L-threo-4-Methylsulfonylphenylserine Ethyl Ester of High Optical Purity

Li-Chao Wang et al.

Summary: By rational design, researchers successfully screened a mutant LTA with enhanced C-beta-stereoselectivity, improving the efficiency of synthesizing (2S, 3R)-1b. Furthermore, esterification was used to successfully synthesize high-purity (2S, 3R)-1d, providing an effective method for green synthesis.

MOLECULAR CATALYSIS (2022)

Article Biochemistry & Molecular Biology

Computer-aided directed evolution of L-threonine aldolase for asymmetric biocatalytic synthesis of a chloramphenicol intermediate

Baoqin Cai et al.

Summary: This study employs computer-aided directed evolution to enhance the activity, selectivity, and stability of L-threonine aldolase for the synthesis of (R,S)-AHNPA. The improved aldolase variant achieved a high conversion rate with cheap achiral precursors at a large scale.

BIOORGANIC & MEDICINAL CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

Substrate access path-guided engineering of l-threonine aldolase for improving diastereoselectivity

Wenlong Zheng et al.

Summary: The l-threonine aldolase from Leishmania major was engineered to improve its diastereoselectivity by considering the physico-chemical properties of the substrate access path, leading to significant enhancement in diastereomeric excess (de) value.

CHEMICAL COMMUNICATIONS (2022)

Review Chemistry, Multidisciplinary

Biocatalysis: Enzymatic Synthesis for Industrial Applications

Shuke Wu et al.

Summary: Biocatalysis is widely used as an alternative to chemical catalysis in various fields, with enzymes playing a key role in organic synthesis, particularly in the production of chiral compounds for pharmaceuticals and flavors. Biocatalysts are also utilized on a large scale for the production of specialty and bulk chemicals. This review focuses on scalable chemical production using enzymes, discussing opportunities, limitations, and emerging enzyme classes through illustrative examples.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Physical

Directed Evolution of L-Threonine Aldolase for the Diastereoselective Synthesis of β-Hydroxy-α-amino Acids

Wenlong Zheng et al.

Summary: The study utilized a CAST/ISM strategy to accelerate the directed evolution of LTA by focusing on amino acid residues within the substrate pocket. Significant progress was made in the synthesis of products, showing promise for industrial applications.

ACS CATALYSIS (2021)

Article Chemistry, Multidisciplinary

Improving the Cβ Stereoselectivity of L-Threonine Aldolase for the Synthesis of L-threo-4-Methylsulfonylphenylserine by Modulating the Substrate-Binding Pocket To Control the Orientation of the Substrate Entrance

Lichao Wang et al.

Summary: l-Threonine aldolase from Actinocorallia herbida (AhLTA) is an ideal catalyst for producing l-threo-4-methylsulfonylphenylserine, and engineering the enzyme through a combinatorial active-site saturation test (CAST) and sequence conservatism analysis has successfully improved the C-beta stereoselectivity. The mutant Y314R demonstrated higher diastereomeric excess (de) in asymmetric synthesis, showcasing the potential of directly controlling substrates in the active pocket for industrial applications.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Review Chemistry, Multidisciplinary

Enzymes, In Vivo Biocatalysis, and Metabolic Engineering for Enabling a Circular Economy and Sustainability

Pattarawan Intasian et al.

Summary: The review emphasizes the importance of circular economy as a sustainable solution for manufacturing, converting waste into resources. Understanding how enzymes convert biobased feedstocks into valuable chemicals is crucial for developing greener and cleaner biobased processes in biocatalysis, metabolic engineering, and synthetic biology. The utilization of this knowledge can lead to the transformation of biobased wastes and greenhouse gases into high-value products.

CHEMICAL REVIEWS (2021)

Article Biochemistry & Molecular Biology

Identification and application of threonine aldolase for synthesis of valuable α-amino, β-hydroxy-building blocks

Mathieu Ligibel et al.

BIOCHIMICA ET BIOPHYSICA ACTA-PROTEINS AND PROTEOMICS (2020)

Article Engineering, Chemical

An L-threonine aldolase for asymmetric synthesis of β-hydroxy-α-amino acids

Li-Chao Wang et al.

CHEMICAL ENGINEERING SCIENCE (2020)

Review Chemistry, Multidisciplinary

Catalytic enantioselective aldol reactions

Yasuhiro Yamashita et al.

CHEMICAL SOCIETY REVIEWS (2018)

Review Biotechnology & Applied Microbiology

Threonine aldolases: perspectives in engineering and screening the enzymes with enhanced substrate and stereo specificities

Kateryna Fesko

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY (2016)

Article Chemistry, Physical

Building Bridges: Biocatalytic C-C-Bond Formation toward Multifunctional Products

Nina G. Schmidt et al.

ACS CATALYSIS (2016)

Article Biochemistry & Molecular Biology

Molecular basis of E-coli L-threonine aldolase catalytic inactivation at low pH

Soumya G. Remesh et al.

BIOCHIMICA ET BIOPHYSICA ACTA-PROTEINS AND PROTEOMICS (2015)

Article Biochemistry & Molecular Biology

On the catalytic mechanism and stereospecificity of Escherichia coli L-threonine aldolase

Martino L. di Salvo et al.

FEBS JOURNAL (2014)

Article Biochemical Research Methods

L-allo-Threonine aldolase with an H128Y/S292R mutation from Aeromonas jandaei DK-39 reveals the structural basis of changes in substrate stereoselectivity

Hui-Min Qin et al.

ACTA CRYSTALLOGRAPHICA SECTION D-BIOLOGICAL CRYSTALLOGRAPHY (2014)

Review Chemistry, Physical

Biocatalytic Methods for CC Bond Formation

Kateryna Fesko et al.

CHEMCATCHEM (2013)

Review Biochemical Research Methods

Novel carbon-carbon bond formations for biocatalysis

Verena Resch et al.

CURRENT OPINION IN BIOTECHNOLOGY (2011)

Review Chemistry, Medicinal

Marine Biocatalysts: Enzymatic Features and Applications

Antonio Trincone

MARINE DRUGS (2011)

Article Chemistry, Organic

An efficient enantioselective synthesis of florfenicol via asymmetric aziridination

Zhonghua Wang et al.

TETRAHEDRON (2011)

Review Biotechnology & Applied Microbiology

Threonine aldolases-screening, properties and applications in the synthesis of non-proteinogenic beta-hydroxy-alpha-amino acids

Nina Dueckers et al.

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY (2010)

Article Biotechnology & Applied Microbiology

Diastereoselective synthesis of l-threo-3,4-dihydroxyphenylserine by low-specific l-threonine aldolase mutants

Hui-Jeong Gwon et al.

BIOTECHNOLOGY LETTERS (2010)

Review Chemistry, Multidisciplinary

The direct catalytic asymmetric aldol reaction

Barry M. Trost et al.

CHEMICAL SOCIETY REVIEWS (2010)

Article Biotechnology & Applied Microbiology

Novel Alkane Hydroxylase Gene (alkB) Diversity in Sediments Associated with Hydrocarbon Seeps in the Timor Sea, Australia

Kenneth Wasmund et al.

APPLIED AND ENVIRONMENTAL MICROBIOLOGY (2009)

Review Chemistry, Multidisciplinary

Catalytic asymmetric aldol reactions in aqueous media

Jacek Mlynarski et al.

CHEMICAL SOCIETY REVIEWS (2008)

Article Chemistry, Organic

Threonine aldolases -: an emerging tool for organic synthesis

Johannes Steinreiber et al.

TETRAHEDRON (2007)

Article Chemistry, Inorganic & Nuclear

Improved preparation of β-hydroxy-α-amino acids:: direct formation of sulfates by sulfuryl chloride

M Alonso et al.

TETRAHEDRON-ASYMMETRY (2005)

Article Biochemistry & Molecular Biology

X-ray structures of threonine aldolase complexes: Structural basis of substrate recognition

CL Kielkopf et al.

BIOCHEMISTRY (2002)