Article
Chemistry, Multidisciplinary
Ji-Yuan Du, Tudor Balan, Tim D. W. Claridge, Martin D. Smith
Summary: This study presents a highly enantioselective and ring-closing synthesis of medium ring lactams, utilizing an intramolecular counterion-directed C-alkylation reaction. The resulting product contains complex chiral elements and is formed through an enolate-driven configurational relaxation process to achieve alkylative ring closure.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Biochemistry & Molecular Biology
Bochun Hu, Xiuxiu Zhu, Dong Zhang, Wenqian Lin, Mengdi Wu, Minchen Wu
Summary: By adding suitable surfactants, organic solvents, and deep eutectic solvents into the reaction media, the enantioconvergent hydrolysis of (R)-phenyl-1,2-ethanediol can be effectively achieved on a gram scale. The identified reaction medium can also be applied to similar hydrolytic reactions.
PROCESS BIOCHEMISTRY
(2022)
Article
Biotechnology & Applied Microbiology
Rui Huang, Chuang Li, Shi-Guang Zhao, Qing-Tao Liu, Yan Liu, Zheng-Lian Xue
Summary: A novel microbial epoxide hydrolase, SfEH1, was identified and overexpressed in E. coli. The enzyme showed higher activity and more significant temperature and pH dependence compared to whole E. coli cells. It displayed high regioselectivity and conversion ratio towards rac-1,2-epoxyoctane and (R)-1,2-pentanediol ((R)-1,2-hexanediol).
ENZYME AND MICROBIAL TECHNOLOGY
(2023)
Article
Chemistry, Physical
Jieran Yi, Zilong Wang, Zhi Li
Summary: Enantioconvergent conversions of rac-styrene oxides to (R)-mandelic acids were achieved using an enzymatic cascade, resulting in high yields. The concept was proven using a mixture of enzymes or coupled E. coli strains.
Article
Chemistry, Physical
Zheng Wen, Bo-Chun Hu, Die Hu, You-Yi Liu, Dong Zhang, Jia Zang, Min-Chen Wu
Summary: A putative Solanum lycopersicum epoxide hydrolase, SlEH2, was discovered and successfully expressed in E. coli based on computer-aided analysis. The E. coli transformant expressing SIEH2 demonstrated high activity and enantiomeric selectivity, allowing for successful substrate resolution under specific conditions.
CATALYSIS COMMUNICATIONS
(2021)
Article
Biotechnology & Applied Microbiology
Xiu-Xiu Zhu, Bo-Chun Hu, Wen-Qian Lin, Dong Zhang, Jun Zhao, Min-Chen Wu
Summary: The study focused on enhancing the regioselectivity of RpEH for specific substrates by fine-tuning its substrate-binding pocket, resulting in the production of the target product (R)-mNPED with a high yield of 95.7% and enantiomeric excess of 93.4%.
BIOCHEMICAL ENGINEERING JOURNAL
(2022)
Article
Multidisciplinary Sciences
Jun-Kuan Li, Ge Qu, Xu Li, Yuchen Tian, Chengsen Cui, Fa-Guang Zhang, Wuyuan Zhang, Jun-An Ma, Manfred T. Reetz, Zhoutong Sun
Summary: This study presents an in silico strategy for the synthesis of chiral N- and O-heterocycles using a modified limonene epoxide hydrolase as a catalyst. By reshaping the active site, the reprogrammed enzyme enables the catalysis of Baldwin-type cyclizations, leading to high conversion rates and enantiomeric ratios.
NATURE COMMUNICATIONS
(2022)
Article
Environmental Sciences
Shanshan Di, Zhenzhen Liu, Huiyu Zhao, Ying Li, Peipei Qi, Zhiwei Wang, Hao Xu, Yuanxiang Jin, Xinquan Wang
Summary: The tire antidegradant 6PPD and its transformation product 6PPD-Q are highly toxic to aquatic organisms. Their toxicities are species-specific, and the enantiomers of 6PPD do not exhibit enantioselective hydrolysis or toxicity. The formation concentrations of 6PPD-Q in water solutions exceed the median lethal concentrations of certain fish species, raising concerns for environmental risk assessments.
ENVIRONMENT INTERNATIONAL
(2022)
Article
Chemistry, Multidisciplinary
Yuan Cai, Shi-Liang Shi
Summary: The study revealed a novel method for upgrading simple racemic secondary alcohols to enantioenriched tertiary alcohols, using an NHC-nickel catalyst to achieve efficient asymmetric alcohol alpha-C-H arylation, followed by asymmetric addition of arylboronic esters after dehydrogenation. Mechanistic studies and control experiments were conducted to understand the exceptional control over chemo- and enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Agricultural Engineering
Ye Rim Park, Shyam Krishna, Ok Kyung Lee, Eun Yeol Lee
Summary: This study investigated the epoxidation efficacy of different types of methanotrophs and found that type II methanotrophs are more efficient in converting alkenes to epoxides. By overexpressing epoxide hydrolases (EHs) of different origins in type II methanotrophs, 1,2-diols were successfully synthesized from epoxides. This demonstrates the potential of using methanotrophs as a microbial platform for diol production and the development of continuous bioreactors for industrial applications.
BIORESOURCE TECHNOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Peng Lu, Hongliang Wang, Yihui Mao, Xin Hong, Zhan Lu
Summary: Investigation on asymmetric hydrogenation of olefins is vital for the synthesis of pharmaceutical molecules and chemical industry. A cobalt-catalyzed enantioconvergent hydrogenation method has been developed for common minimally functionalized E/Z-olefin mixtures.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Biotechnology & Applied Microbiology
Hakan Onur, Ahmet Tulek, Elif Sibel Aslan, Baris Binay, Deniz Yildirim
Summary: In this study, an epoxide hydrolase gene from the extremophile Hypsibius dujardini was heterologously expressed in Pichia pastoris and immobilized in a metal-organic framework. The immobilized enzyme showed higher stability and enantioselectivity.
BIOCHEMICAL ENGINEERING JOURNAL
(2022)
Review
Chemistry, Multidisciplinary
Miguel Yus, Carmen Najera, Francisco Foubelo, Jose M. Sansano
Summary: Enantioconvergent catalysis is a new method to convert racemic compounds into a single enantiomer, allowing various reactions such as cross-coupling, C-H functionalization, etc. Hydroalkylation serves as an alternative to reactions like cross-coupling. Other metal-catalyzed reactions include amination, addition reactions, hydroxylation, etc.
Article
Chemistry, Multidisciplinary
Juan Zhang, Min Zhang, Xiao-Kui Huo, Jing Ning, Zhen-Long Yu, Christophe Morisseau, Cheng-Peng Sun, Bruce D. Hammock, Xiao-Chi Ma
Summary: Soluble epoxide hydrolase (sEH) plays a critical role in inflammation by modulating levels of epoxyeicosatrienoic acids (EETs) and other epoxy fatty acids (EpFAs). Wedelolactone (WED), a small molecule, targets sEH, suppresses its activity, and enhances EET levels, attenuating inflammation and oxidative stress. In an LPS-stimulated ALI animal model, pharmacological sEH inhibition or sEH knockout alleviates pulmonary damage, suppresses macrophage activation, and reduces inflammation and oxidative stress.
ACS CENTRAL SCIENCE
(2023)
Review
Biochemistry & Molecular Biology
Marek Bucko, Katarina Kaniakova, Helena Hronska, Peter Gemeiner, Michal Rosenberg
Summary: This review discusses the state of the art and development potential of epoxide hydrolases as biocatalysts, focusing on their application as chiral building blocks for bioactive compounds and drugs. The review covers new approaches to discover epoxide hydrolases using genome mining and enzyme metagenomics, as well as techniques to improve enzyme activity, enantioselectivity, enantioconvergence, and thermostability. The study also explores possibilities for expanding the synthetic capabilities of epoxide hydrolases through non-natural enzyme cascade reactions.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Agricultural Engineering
Arslan Sarwar, Linh Thanh Nguyen, Eun Yeol Lee
Summary: This study demonstrates the efficient upgrading of ethanol to fatty acid ethyl esters (FAEEs) using Pseudomonas putida KT2440, achieving high yields through gene expression and culture optimization. It provides a basis for integrating bioethanol production with the efficient conversion of ethanol to biodiesel.
BIORESOURCE TECHNOLOGY
(2022)
Article
Engineering, Environmental
Diep Ngoc Pham, Dung Hoang Anh Mai, Anh Duc Nguyen, Tin Hoang Trung Chau, Eun Yeol Lee
Summary: The study engineered a methane-oxidizing bacterium to produce plant growth hormones from methane, promoting plant growth and enhancing salt-alkaline tolerance. In addition, xylose as a co-substrate was found to increase product titers.
CHEMICAL ENGINEERING JOURNAL
(2022)
Article
Agricultural Engineering
Hoa Thi Quynh Le, Eun Yeol Lee
Summary: The study explores the metabolic pathways of methane and methanol to produce 1,2-propanediol (1,2-PDO) using the type I methanotroph Methylotuvimicrobium alcaliphilum 20Z. It finds that the carbon flux from methane to the EMP pathway restricts the production of 1,2-PDO. Co-utilization of C1 substrates and glycerol enhances the production of 1,2-PDO, although lactate is co-produced in higher amounts. The study provides insights into metabolic routes for 1,2-PDO and lactate co-production from C1 and C3 compounds in methanotrophs.
BIORESOURCE TECHNOLOGY
(2022)
Article
Engineering, Environmental
Jiyeong Jeong, Tae Hyun Kim, Nulee Jang, Minji Ko, Seong Keun Kim, Georgii Emelianov, Eugene Rha, Kil Koang Kwon, Haseong Kim, Eun Yeol Lee, Dae-Hee Lee, Hyewon Lee, Seung-Goo Lee
Summary: Methanotrophs have been successfully engineered to produce valuable bioproducts from methane by utilizing a phenol-inducible gene expression system and a CRISPR-based genome editing tool. The engineered strain achieved the highest concentration of synthetic biochemicals produced from methane in methanotrophs.
CHEMICAL ENGINEERING JOURNAL
(2023)
Review
Engineering, Environmental
Diep Ngoc Pham, Anh Duc Nguyen, Eun Yeol Lee
Summary: Methane and carbon dioxide are the most abundant greenhouse gases, and reducing their emissions is crucial for mitigating climate change. Utilizing methylotrophic bacteria-based technologies to capture and utilize these gases shows promise in lowering their concentrations. This article highlights the advantages of methylotrophs in bioconversion of methane, CO2, methanol, and formate, and discusses innovative strategies to improve conversion efficiency.
CHEMICAL ENGINEERING JOURNAL
(2022)
Article
Chemistry, Applied
Van Nhieu Le, Dieu-Phuong Phan, Seung-Soo Kim, Eun Yeol Lee, Jinsoo Kim
Summary: By using response surface methodology combined with the central composite design, the operating conditions for catalytic hydrodeoxygenation of anisole were optimized, resulting in high conversion rates. It was found that temperature had the greatest effect on the conversion rate.
FUEL PROCESSING TECHNOLOGY
(2022)
Article
Biochemistry & Molecular Biology
Linh Thanh Nguyen, Dung Hoang Anh Mai, Arslan Sarwar, Eun Yeol Lee
Summary: This study constructed a production pathway for short-chain-length polyhydroxyalkanoates (PHAs) in P. putida KT2440 and enhanced the product yield by reconstructing the ethanol catabolic pathway. Transcriptome analysis was conducted to gain insights into central metabolic pathways and gene expression patterns in response to substrate changes. Furthermore, the potential of P. putida KT2440 for producing copolymers from different carbon sources was demonstrated.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2022)
Article
Genetics & Heredity
Dung Hoang Anh Mai, Linh Thanh Nguyen, Eun Yeol Lee
Summary: NLP models have been used to predict and analyze the promoters in freshwater cyanobacteria, with the help of a custom pipeline and an integrated platform. The models achieved high AUROC and F1 scores, indicating their effectiveness in understanding the sequential structure of DNA.
FRONTIERS IN GENETICS
(2022)
Review
Biotechnology & Applied Microbiology
Ushasree Mrudulakumari Vasudevan, Dung Hoang Anh Mai, Shyam Krishna, Eun Yeol Lee
Summary: Methanotrophs have the potential to produce various bioactive secondary metabolites including iso-prenoids, polymers, peptides, and vitamins. Genome mining of these microbes revealed the hidden biosynthetic potential of these microbes. Through advanced synthetic biology tools, the central carbon metabolism in methanotrophs can be modified to produce valuable secondary metabolites. This review summarizes the possibilities of developing methanotrophs as microbial chassis for high-value secondary metabolites.
BIOTECHNOLOGY ADVANCES
(2023)
Review
Chemistry, Multidisciplinary
My Ha Tran, Eun Yeol Lee
Summary: This article reviews the methods for producing polyols from vegetable oil, lignin, and carbohydrates, as well as the production of polyurethane from biomass polyols. Conversion of vegetable oil involves epoxidation, hydroformylation, and transesterification, while conversion of lignin involves solvothermal liquefaction, hydroxymethylation, oxypropylation, and phenolation.
ENVIRONMENTAL CHEMISTRY LETTERS
(2023)
Article
Multidisciplinary Sciences
Sanzhar Naizabekov, Seung Woon Hyun, Jeong-Geol Na, Sukhwan Yoon, Ok Kyung Lee, Eun Yeol Lee
Summary: Comparative genomic analysis revealed the potential of newly isolated methanotroph Methylocystis sp. MJC1 as a biodegradable polyhydroxybutyrate (PHB) producer. Under nitrogen-limiting conditions, Methylocystis sp. MJC1 can accumulate up to 44.5% PHB based on dry cell weight. Functional annotation and comparison with other Methylocystis species showed that Methylocystis sp. MJC1 contains all major biochemical pathways of type II methanotrophs and possesses both particulate and soluble methane monooxygenases, which are not commonly found in other Methylocystis species. These findings open up possibilities for future practical applications such as organism-specific genome-scale models and metabolic engineering strategies.
Article
Chemistry, Multidisciplinary
Dieu-Phuong Phan, My Ha Tran, Eun Yeol Lee
Summary: Polymeric materials play a crucial role in modern society, and biomass can be utilized as a renewable carbon source for the production of bio-based plastics. This review summarizes the applications of Metal-Organic Framework (MOF)-based catalysts in the production of renewable bio-plastic-derived materials and highlights the effects of reaction conditions.
MATERIALS TODAY CHEMISTRY
(2023)
Article
Biotechnology & Applied Microbiology
Arslan Sarwar, Eun Yeol Lee
Summary: Methanol is gaining attention as a potential carbon substrate for the production of fuels and chemicals due to its high reduction degree, abundance, and low price. Both native and synthetic methylotrophic microorganisms have been investigated for the production of biofuels and chemicals. However, the complex metabolic pathways, limited availability of genetic tools, and toxicity issues still pose challenges for achieving high-level production for commercial purposes. This article reviews the production of biofuels and chemicals from methanol by native and synthetic methylotrophs and discusses ways to improve their efficiency.
SYNTHETIC AND SYSTEMS BIOTECHNOLOGY
(2023)
Article
Biotechnology & Applied Microbiology
Tin Hoang Trung Chau, Anh Duc Nguyen, Eun Yeol Lee
Summary: Using bioinformatics tools, the protein PmoD was elucidated as a membrane protein with the proposed function as a transport protein. Furthermore, the assays of PmoD-heterologously expressed Methylomonas sp. DH-1 as a whole-cell biocatalyst validated the coupling activity of PmoD with pMMO to convert acetone to acetol, unlocking the potential of this recombinant biocatalyst for acetol production. The proposed acetone-assimilated pathway in the recombinant Methylomonas sp. DH-1, once validated, can extend the metabolic flexibility of Methylomonas sp. DH-1.
BIOTECHNOLOGY FOR BIOFUELS AND BIOPRODUCTS
(2022)
Article
Chemistry, Multidisciplinary
Diep Ngoc Pham, Anh Duc Nguyen, So Hyeon Oh, Eun Yeol Lee
Summary: In this study, metabolic engineering was used for the first time to produce indigo and alpha-farnesene from methane. By addressing the bottlenecks in the shikimate and MEP pathways, the production of indigo and alpha-farnesene was significantly enhanced. The use of xylose as a co-substrate restored the impaired growth of recombinants. This work provides potential approaches to improve natural compound production from renewable carbon sources.
