Pepsin-catalyzed direct asymmetric aldol reactions for the synthesis of vicinal diol compounds

Li, Lingyu; Yang, Da‐Cheng; Guan, Zhi; He, Yan‐Hong

doi:10.1016/j.tet.2015.01.061

Cited by 13 publications

(3 citation statements)

References 41 publications

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“…The study of asymmetric aldol reactions has grown in the last decades, making this type of reaction one of the most investigated in organic synthesis. − They are an important tool to make new carbon–carbon bonds and to control the stereochemistry of the stereogenic centers generated. In a simplified way, the aldol reactions are based on joining two relatively simple molecules to give rise to a more complex one, that is, the β-hydroxy carbonylated compounds (aldol compounds). , These compounds can be used in different areas such as pharmaceutical, cosmetic, flavors, and additives industries. − …”

Section: Introductionmentioning

confidence: 99%

Phase Behavior for the System Carbon Dioxide + p-Nitrobenzaldehyde: Experimental and Modeling

et al. 2019

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The experimental study and thermodynamic modeling of the phase behavior of pressurized reactional systems allows the optimization of several unit operations involved in the process of product formation. In this work, experimental data of phase equilibria for the CO 2 + p-nitrobenzaldheyde binary system were obtained through the static synthetic method. The range of temperature, pressure, and p-nitrobenzaldehyde molar fraction investigated were 281−353 K, 6.5−25.0 MPa, and 2.638 × 10 −3 to 5.903 × 10 −3 , respectively. A model previously developed to describe asymmetric mixtures presenting fluid and solid phases was applied to describe the phase behavior of the system. This model uses the Peng−Robinson equation of state (PR-EoS) to describe the properties of the fluid phases and an expression for the fugacity of p-nitrobenzaldehyde as a pure solid for the solid phase. Different model parametrization strategies were studied, and complete isopleths were calculated considering the fluid−fluid, solid−fluid, and solid−fluid−fluid phase equilibria over wide ranges of temperature and pressure. The experimental results showed nonmonotonic (local minimum) solid−fluid phase behavior for all mixture compositions investigated. The model employed and the parametrization strategies were able to describe the experimentally observed phase behavior.

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Section: Introductionmentioning

confidence: 99%

Phase Behavior for the System Carbon Dioxide + p-Nitrobenzaldehyde: Experimental and Modeling

et al. 2019

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“…Our group also has investigated the catalytic promiscuity of pepsin. In 2015, we found that pepsin can catalyze direct asymmetric aldol reactions for the synthesis of vicinal diol compounds, and products were obtained with an enantioselectivity of up to 75% ee . In 2016, we reported the pepsin-catalyzed Morita–Baylis–Hillman (MBH) reaction between aromatic aldehydes and 2-cyclohexen-1-one or 2-cyclopenten-1-one, and an enantioselectivity of up to 38% ee was achieved .…”

Section: Introductionmentioning

confidence: 99%

“…In 2015, we found that pepsin can catalyze direct asymmetric aldol reactions for the synthesis of vicinal diol compounds, and products were obtained with an enantioselectivity of up to 75% ee. 23 In 2016, we reported the pepsin-catalyzed Morita−Baylis−Hillman (MBH) reaction between aromatic aldehydes and 2cyclohexen-1-one or 2-cyclopenten-1-one, and an enantioselectivity of up to 38% ee was achieved. 24 Very recently, we found that pepsin can catalyze the domino Knoevenagel/ Michael/Michael reaction for the synthesis of spirooxindole derivatives with diastereoselectivities of up to >99:1 dr without enantioselectivity.…”

Section: ■ Introductionmentioning

confidence: 99%

Enzyme-Catalyzed Asymmetric Domino Thia-Michael/Aldol Condensation Using Pepsin

et al. 2016

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The novel catalytic promiscuity of pepsin from porcine gastric mucosa for the asymmetric catalysis of the domino thia-Michael/aldol condensation reaction in MeCN and buffer was discovered for the first time. Broad substrate specificity was tested, and a series of corresponding products were obtained with enantioselectivities of up to 84% ee. This specific catalysis was demonstrated by using recombinant pepsin and control experiments with denatured and inhibited pepsin. The reaction was also shown to occur in the active site by site-directed mutagenesis (the Asp32Ala mutant of pepsin), and a possible mechanism was proposed.

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Solvent‐Controlled Enzyme‐Catalyzed Friedel–Crafts Reactions of Indoles and Isatins by Using α‐Chymotrypsin

Xue

Guo

et al. 2017

Asian J Org Chem

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Friedel-Crafts reactions between isatins and indoles catalyzed by a-chymotrypsin from bovine pancreas (BPC) are described. The reaction could be controlled by judicious choice of the solvent. 3-Hydroxy-oxindoles and 3,3bis(indol-3-yl)indolin-2-ones were obtained in aprotic (DCE) and protic solvent( MeOH), respectively;t he reactions pro-ceeded at 30 8Cw ith ab road substrate scope in each case. Severalp harmacologically active products were obtained in protic solvent. This method has the potentialt ob ecome as imple, practical procedure fort he synthesis of 3-hydroxyoxindole and 3,3-bis(indol-3-yl)indolin-2-one derivatives.Scheme1.Natural products that contain the 3-hydroxy-2-oxindole structural unit. Scheme2.Representative examples of pharmacologically active 3,3-bis(indol-3-yl)indolinones.[a] J.

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Pepsin-catalyzed direct asymmetric aldol reactions for the synthesis of vicinal diol compounds

Cited by 13 publications

References 41 publications

Phase Behavior for the System Carbon Dioxide + p-Nitrobenzaldehyde: Experimental and Modeling

Phase Behavior for the System Carbon Dioxide + p-Nitrobenzaldehyde: Experimental and Modeling

Enzyme-Catalyzed Asymmetric Domino Thia-Michael/Aldol Condensation Using Pepsin

Solvent‐Controlled Enzyme‐Catalyzed Friedel–Crafts Reactions of Indoles and Isatins by Using α‐Chymotrypsin

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