Biocatalytic asymmetric Mannich reaction of ketimines using wheat germ lipase

Wu, Lingling; Xiang, Yang; Yang, Da‐Cheng; Guan, Zhi; He, Yan‐Hong

doi:10.1039/c5cy01923k

Cited by 43 publications

(23 citation statements)

References 66 publications

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“…An addition to the toolbox of lipase catalyzed Mannich reaction has been done lately by He et al. who reported a highly enantioselective synthesis of β‐amino ketones by the reaction between 3‐substituted‐2H‐1,4‐benzoxazines and acetone ( Scheme ) …”

Section: Introductionmentioning

confidence: 99%

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Promiscuity of Lipase‐Catalyzed Reactions for Organic Synthesis: A Recent Update

et al. 2018

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Lipase-catalyzed organic reactions have widely been practiced in the past three decades. In addition to its wide acceptance in conventional reactions such as hydrolysis, transesterification, and enantiopure synthesis (kinetic resolution and dynamic kinetic resolution) several reports on the catalytic promiscuity of lipases have also been published. The concept of promiscuity, where lipase catalyzes reactions beyond its natural function, has been perceived as a useful phenomenon which can enhance the utility of lipase as a biocatalyst. Many useful organic reactions such as Aldol condensation, Hantzsch reaction, Canizzaro reaction, Mannich reaction, Baylis-Hillman reaction, Knoevenagel condensation, Michael addition, Ugi reaction, and oxidation catalyzed by lipases have surfaced in the literature. The current review is a critical compilation of such research findings to put forth the synthetic applications of lipase, beyond the orthodox biocatalytic toolbox.

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Section: Introductionmentioning

confidence: 99%

“…An enolate is formed by the transfer of a proton from acetone to Ser. This enolate is attacked by the protonated ketimine to yield the Mannich product …”

Section: Introductionmentioning

confidence: 99%

Promiscuity of Lipase‐Catalyzed Reactions for Organic Synthesis: A Recent Update

et al. 2018

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“…Although numerous flavin adenine dinucleotide (FAD)-dependent amine oxidases have been characterized to date 9 , to our knowledge LkcE is only the second described amide oxidase 10 . This observation, coupled with the fact that no other known enzyme carries out Mannich chemistry except as a promiscuous activity 11 , motivated our interest in establishing a detailed structure/function relationship for LkcE.…”

Section: Introductionmentioning

confidence: 99%

Insights into a dual function amide oxidase/macrocyclase from lankacidin biosynthesis

et al. 2018

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Acquisition of new catalytic activity is a relatively rare evolutionary event. A striking example appears in the pathway to the antibiotic lankacidin, as a monoamine oxidase (MAO) family member, LkcE, catalyzes both an unusual amide oxidation, and a subsequent intramolecular Mannich reaction to form the polyketide macrocycle. We report evidence here for the molecular basis for this dual activity. The reaction sequence involves several essential active site residues and a conformational change likely comprising an interdomain hinge movement. These features, which have not previously been described in the MAO family, both depend on a unique dimerization mode relative to all structurally characterized members. Taken together, these data add weight to the idea that designing new multifunctional enzymes may require changes in both architecture and catalytic machinery. Encouragingly, however, our data also show LkcE to bind alternative substrates, supporting its potential utility as a general cyclization catalyst in synthetic biology.

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“…Wheat germ lipase (WGL) catalyzed a highly enantioselective Mannich reaction between 3‐substituted‐2 H ‐1,4‐benzoxazines and acetone . The WGL‐catalyzed Mannich reaction gave the Mannich adduct with excellent enantioselectivity, which was decreased by the addition of water into the reaction mixture.…”

Section: Classification Based On Catalytic Systemmentioning

confidence: 99%

Recent Developments and Perspectives in the Asymmetric Mannich Reaction

et al. 2018

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The asymmetricM annichr eactioni savery important method for CÀCb ond formation,a nd it is the classical method for the preparation of b-amino ketones and aldehydes. The resulting b-amino carbonyl compounds are widely found in nature, which attests to the importance of this reaction. This Focus Review providesa no verview of asymmetricM annich reactions, the various catalysts that have been used, and its applications,f or papers published since 2013. Scheme1.The Mannich reaction.Scheme2.The mechanism of the Mannich reaction;reproduced with permissionfrom Ref.[1]. andhi University. His research interests are in the areaso fo rganic synthesis, medicinal chemistry,a nd catalysis, in particularr uthenium-, iron-, zinc-, and copper-catalyzedr eactions. His h-index is 24.

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Biocatalytic asymmetric Mannich reaction of ketimines using wheat germ lipase

Abstract: Wheat germ lipase (WGL) was used for the first time as a biocatalyst in asymmetric Mannich reaction of ketimines.

Cited by 43 publications

References 66 publications

Promiscuity of Lipase‐Catalyzed Reactions for Organic Synthesis: A Recent Update

Promiscuity of Lipase‐Catalyzed Reactions for Organic Synthesis: A Recent Update

Insights into a dual function amide oxidase/macrocyclase from lankacidin biosynthesis

Recent Developments and Perspectives in the Asymmetric Mannich Reaction

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