Benzaldehyde lyase-catalyzed enantioselective C–C bond formation and cleavage: A review

Zhang, Ju; Xu, Junde; Li, Zhi-Yun; Fang, Jingjie; Li, Menglan; Howell, Daniel C.; Chen, Fen‐Er

doi:10.1016/j.gresc.2022.05.011

Cited by 8 publications

(4 citation statements)

References 37 publications

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“…It is known that the absolute configurations of chiral drug molecules play an important role in their bioactivities in living organisms. Chiral pesticide enantiomers exhibit stereoselective differences in their bioactivity, toxicity, biodegradation, enrichment, and ecotoxicology within chiral environments. − In the unique chiral environment within organisms, the stereoselectivity of enzymes dictates that only pesticide or intermediate configurations matching enzyme configurations yield effective effects. , Therefore, developing enantio-pure chiral pesticides has become significant in the search for novel pesticides with high efficiency and low risk. − …”

Section: Introductionmentioning

confidence: 99%

Discovery of Novel Chiral Indole Derivatives Containing the Oxazoline Moiety as Potential Antiviral Agents for Plants

Huang,

Peng,

Chen

et al. 2024

J. Agric. Food Chem.

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Potato virus Y (PVY) is an important plant virus that has spread worldwide, causing significant economic losses. To search for novel structures as potent antiviral agents, a series of chiral indole derivatives containing oxazoline moieties were designed and synthesized and their anti-PVY activities were evaluated. Biological activity tests demonstrated that many chiral compounds exhibited promising anti-PVY activities and that their absolute configurations exhibited obvious distinctions in antiviral bioactivities. Notably, compound (S)-4v displayed excellent curative and protective efficacy against PVY, with EC50 values of 328.6 and 256.1 μg/mL, respectively, which were superior to those of commercial virucide ningnanmycin (NNM, 437.4 and 397.4 μg/mL, respectively). The preliminary antiviral mechanism was investigated to determine the difference in antiviral activity between the two enantiomers of 4v chiral compounds. Molecular docking indicated a stronger binding affinity between the coating proteins of PVY (PVY-CP) and (S)-4v (−6.5 kcal/mol) compared to (R)-4v (−6.2 kcal/mol). Additionally, compound (S)-4v can increase the chlorophyll content and defense-related enzyme activities more effectively than its enantiomer. Therefore, this study provides an important basis for the development of chiral indole derivatives containing oxazoline moieties as novel agricultural chemicals.

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Section: Introductionmentioning

confidence: 99%

Discovery of Novel Chiral Indole Derivatives Containing the Oxazoline Moiety as Potential Antiviral Agents for Plants

Huang,

Peng,

Chen

et al. 2024

J. Agric. Food Chem.

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“…19 Therefore, it is significant to prepare the enantiomerically pure molecules for pharmaceutical and agricultural applications. [20][21][22][23][24][25][26][27][28][29][30] Up to now, numerous research works on chiral agrochemicals have been realized, but examples of chiral antiviral molecules remain limited. [31][32][33] In 2016, Song and co-workers 34 synthesized a series of ⊍-aminophosphonates with a stereogenic center, exhibiting excellent activity against Cucumber Mosaic Virus (CMV).…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and Anti‐PVY activity of planar chiral thiourea derivatives incorporated with [2.2]Paracyclophane

Shu,

Lv,

Chen

et al. 2024

Pest Management Science

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BACKGROUNDPotato virus Y (PVY) stands as a prominent representative in the realm of plant viruses. It can inflict severe damage upon Solanaceae plants, leading to global dissemination and substantial economic losses. To discover the new antiviral agents, a class of planar chiral thiourea molecules through the key step of N‐heterocyclic carbene‐catalyzed nitrile formation reaction were synthesized with excellent optical purities for antiviral evaluations against plant virus PVY.RESULTSThe absolute configurations of the planar chiral compounds have exhibited obvious distinctions in the anti‐PVY activities. Notability, compound (S)‐4u exhibited remarkable curative activities against PVY, with the half maximal effective concentration values of 349.3 μg/mL, which was better than that of the ningnanmycin with the EC50 values of 400.8 μg/mL. Additionally, The EC50 value for the protective effects of (S)‐4u was 146.2 μg/mL, which was superior to that of NNM (276.4 μg/mL). Furthermore, the mechanism of action of enantiomers of planar chiral compound 4u was investigated through molecular docking, defensive enzyme activity tests and chlorophyll content tests.CONCLUSIONBiological mechanism studies have demonstrated that the configuration of planar chiral target compounds plays a crucial role in the molecular interaction with PVY‐CP, enhancing the activity of defense enzymes and affecting chlorophyll content. The current study has provided significant insights into the roles played by planar chiralities in plant protection against viruses. This paves the way for the development of novel green pesticides bearing planar chiralities with excellent optical purities.This article is protected by copyright. All rights reserved.

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“…23 team has conducted extensive research on the catalytic ability of BAL in C−C bond-forming and bond-cleaving reactions in organic chemistry. 26 These studies prompted us to investigate a biocatalytic approach for the enantioselective synthesis of efinaconazole via BAL-catalyzed epoxide formation, utilizing cost-effective 2,4-difluorobenzaldehyde and acetaldehyde as starting materials. In this study, we have developed a process that allows for the safe, robust, and cost-effective preparation of efinaconazole while also reducing its environmental impact.…”

mentioning

confidence: 99%

“…It is particularly useful in converting a diverse range of ketones and aldehydes into chiral α-hydroxy ketones for pharmaceuticals. Michael Müller’s team has conducted extensive research on the catalytic ability of BAL in C–C bond-forming and bond-cleaving reactions in organic chemistry . These studies prompted us to investigate a biocatalytic approach for the enantioselective synthesis of efinaconazole via BAL-catalyzed epoxide formation, utilizing cost-effective 2,4-difluorobenzaldehyde and acetaldehyde as starting materials.…”

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confidence: 99%

A Chemo-Enzymatic Approach for Preparing Efinaconazole with High Optical Yield

Ju,

Li,

et al. 2023

J. Org. Chem.

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Herein, we present a novel and ecofriendly biocatalytic approach for synthesizing efinaconazole (7), a clinically used antifungal agent. This method involves utilizing benzaldehyde lyase (BAL) to catalyze the crucial benzoin condensation step in the ketone precursor. Treating 2,4-difluorobenzaldehyde with BAL in the presence of thiamin-diphosphate (ThDP) and Mg2+ resulted in the formation of α-hydroxy ketone which then underwent the preparation of 7. This innovative approach not only provides a greener alternative but also offers significant advantages over the traditional chemical process. Through our efforts and development work, we have established efficient and scalable procedures that enable the production of 7 in a moderate 38% yield.

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Benzaldehyde lyase-catalyzed enantioselective C–C bond formation and cleavage: A review

Cited by 8 publications

References 37 publications

Discovery of Novel Chiral Indole Derivatives Containing the Oxazoline Moiety as Potential Antiviral Agents for Plants

Discovery of Novel Chiral Indole Derivatives Containing the Oxazoline Moiety as Potential Antiviral Agents for Plants

Design, synthesis and Anti‐PVY activity of planar chiral thiourea derivatives incorporated with [2.2]Paracyclophane

A Chemo-Enzymatic Approach for Preparing Efinaconazole with High Optical Yield

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