Article
Chemistry, Physical
Elia Calderini, Philipp Suess, Frank Hollmann, Rainer Wardenga, Anett Schallmey
Summary: Multi-step cascade reactions have attracted increasing attention in the field of biocatalysis for achieving high molecular complexity. Enzymatic cascades and organo- or metal catalysts can be combined to expand synthetic routes. Two enantiocomplementary (chemo)-enzymatic cascades were presented, showing high enantioselectivity in the synthesis of chiral aliphatic non-terminal azidoalcohols.
Article
Chemistry, Physical
Fang-Rui Zhang, Nan-Wei Wan, Jin-Mei Ma, Bao-Dong Cui, Wen-Yong Han, Yong-Zheng Chen
Summary: An efficient enzymatic process has been developed for the synthesis of valuable compounds through catalytic kinetic resolution, demonstrating synthetic utility and scalability.
Article
Chemistry, Physical
Irena Dokli, Nevena Milcic, Petra Marin, Marina Svetec Miklenic, Martina Sudar, Lixia Tang, Zvjezdana Findrik Blazevic, Maja Majeric Elenkov
Summary: The kinetic resolution of a series of fluorinated styrene oxide derivatives using halohydrin dehalogenase was studied. A mutant HheC-W249P showed excellent enantioselectivity in catalyzing nucleophilic ring-opening reactions with azide and cyanide ions, yielding various enantiopure beta-substituted alcohols and epoxides. The enzyme demonstrated tolerance to substrates at concentrations over 50 mM, but different side reactions were observed at elevated concentrations and prolonged reaction times. Bio-catalytic azidolysis and cyanolysis of racemic 4-trifluoromethylstyrene oxide on a preparative scale resulted in the production of specific enantiomers with high yields and enantiomeric excesses.
CATALYSIS COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Chuanhua Zhou, Xi Chen, Tong Lv, Xu Han, Jinhui Feng, Weidong Liu, Qiaqing Wu, Dunming Zhu
Summary: In this study, a unique halohydrin dehalogenase (AbHheG) was found to have high activity and alpha/beta-regioselectivity toward the ring opening of racemic styrene oxide with cyanate but with poor stereoselectivity. By reshaping the substrate-binding site of AbHheG, a variant Y15M/N182S was obtained with excellent alpha/beta-regioselectivity and stereoselectivity. This work demonstrated that halohydrin dehalogenase is a useful biocatalyst for the synthesis of both enantiomers of 4-aryl-2-oxazolidinones from readily available racemic styrene oxides.
Article
Chemistry, Organic
Irena Dokli, Zlatko Brkljaca, Petra Svaco, Lixia Tang, Visnja Stepanic, Maja Majeric Elenkov
Summary: This study tested ten different fluorinated aromatic epoxides as potential substrates for halohydrin dehalogenase, showing the synthesis of enantioenriched fluorinated organic compounds in azidolysis reactions. By introducing mutations, the enantioselectivity of the enzyme towards substrates was successfully altered, expanding its application possibilities.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Physical
Lei Wang, Wei Song, Binju Wang, Yan Zhang, Xin Xu, Jing Wu, Cong Gao, Jia Liu, Xiulai Chen, Jinghua Chen, Liming Liu
Summary: A one-pot enzymatic-chemical cascade route was developed to synthesize 2-Hydroxyacetophenone (2-HAP) with a final yield of 92.7%. The introduction of stereospecific carbonyl reductases allowed for further transformation of 2-HAP into (S)- and (R)-1-phenyl-1,2-ethanediol. This method shows potential for synthesizing other valuable chemicals by cascading spontaneous chemical and enzymatic reactions.
Article
Chemistry, Applied
Guo-Zhong Deng, Xu Zhou, Quan-Xiang Yu, Xue-Qing Mou, Miao An, Hai-Bo Cui, Xiao-Jian Zhou, Nan-Wei Wan, Zhi Li, Yong-Zheng Chen
Summary: This article describes a green and efficient method for the synthesis of chiral β-hydroxy nitriles. By using an evolved P450pyr monooxygenase, various pharmaceutically relevant chiral aryl-substituted β-hydroxy nitriles were prepared from alkyl nitriles.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Multidisciplinary Sciences
Yu Wang, Fabiana Subrizi, Eve M. Carter, Tom D. Sheppard, John M. Ward, Helen C. Hailes
Summary: This article reports the design of a parallel enzymatic cascade for the synthesis of halogenated benzylisoquinoline alkaloids, using engineered tyrosinase mutants to enhance substrate capabilities. The method enables the efficient synthesis of halogenated benzylisoquinoline alkaloids with high enantiomeric excess.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Natalia Alcover, Gregorio Alvaro, Marina Guillen
Summary: In this study, asymmetric synthesis of 3-amino-1-phenylbutane (3-APB) was achieved by coupling a transaminase with a pyruvate decarboxylase (PDC) using an in situ by-product removal strategy. The addition of PDC significantly improved the synthesis of 3-APB under optimal reaction conditions, with yields higher than 60% and nearly 90% selectivity achieved. High stereoselectivity for (S)-3-APB was obtained using both CviTA and VflTA.
Article
Chemistry, Multidisciplinary
Zefei Xu, Jinhui Feng, Peiyuan Yao, Qiaqing Wu, Dunming Zhu
Summary: A general chemo-enzymatic approach for the efficient asymmetric synthesis of chiral 3-substituted tetrahydroquinolines has been developed, combining biocatalysis and the Buchwald-Hartwig cross-coupling reaction. The method involves a one-pot ene reductase (ERED)/imine reductase (IRED) cascade and successfully addresses the issue of racemization of the intermediate. This method offers a practical strategy for the construction of chiral 3-substituted tetrahydroquinolines.
Article
Chemistry, Multidisciplinary
Yu Wang, Chengyi Wang, Qipeng Cheng, Yu Su, Hongyu Li, Rui Xiao, Chunxia Tan, Guohua Liu
Summary: The development of a combination enzyme and organocatalyst for aqueous sequential organic transformation is environmentally friendly and overcomes the drawback of only a single methodological approach. The integrated laccase and proline as a chemo-enzymatic co-catalyst system enables efficient oxidation/aldol enantioselective sequential reaction, providing various 1,2-diastereoisomeric chiral beta-hydroxy ketones with acceptable yields and high enantio-/diastereoselectivities.
Article
Chemistry, Physical
Ewald P. J. Jongkind, Aurelie Fossey-Jouenne, Ombeline Mayol, Anne Zaparucha, Carine Vergne-Vaxelaire, Caroline E. Paul
Summary: Accessing chiral amines with high enantiomeric and diastereomeric excess was achieved through the development of a bi-enzymatic cascade using Old Yellow Enzyme family enzymes. Different unsaturated carbonyl substrates were successfully converted with up to 99% selectivity, showcasing the potential of this approach for diverse alkene substrates.
Article
Chemistry, Multidisciplinary
Jian Chen, Gao Deng, You Wang, Shaolin Zhu
Summary: In this study, we have achieved a highly chemo-, regio- and enantioselective reductive hydrocarbonylation of alkenes using a chloroformate ester as a source of CO. This method allows for the rapid increase in molecular complexity and the selective generation of a wide range of structurally diverse alpha-hydroxy ketones, which are important structural elements in bioactive molecules and useful building blocks.
CHINESE JOURNAL OF CHEMISTRY
(2023)
