Investigation of Lipase-Catalyzed Michael-type Carbon-Carbon Bond Formations

G.A. Strohmeier; T. Sovic; G. Steinkellner; Franz Stefan Hartner; Aleksandra Andryushkova; T. Purkarthofer; Anton Glieder; K. Gruber; Herfried Griengl

doi:/10.1016/j.tet.2009.05.042

Investigation of Lipase-Catalyzed Michael-type Carbon-Carbon Bond Formations

G.A. Strohmeier, T. Sovic, G. Steinkellner, Franz Stefan Hartner, Aleksandra Andryushkova, T. Purkarthofer, Anton Glieder, K. Gruber, Herfried Griengl

Research output: Contribution to journal › Article

Abstract

Conjugate additions of carbon nucleophiles to appropriate acceptor molecules were investigated with respect to the synthetic potential and stereochemistry of the products. Reactions of short-chain α,β-unsaturated ketones and mono-substituted nitroalkenes with CH-acidic carboxylic ester derivatives were catalyzed by various immobilized lipases. Using methyl nitroacetate complete conversion with methyl vinyl ketone and trans-β-nitrostyrene was obtained. The reactions proceeded without enantioselectivity. Evidence for enzyme catalysis is provided by the observation that after denaturation of Candida antarctica lipase B or inhibition no reaction took place. Docking studies with the chiral addition product methyl 2-methyl-2-nitro-5-oxohexanoate did not reveal any specific binding mode for this reaction product, which would have been the requirement for stereoselective additions. These results support the experimental findings that the conjugate addition takes place without enantiopreference.

Original language	English
Pages (from-to)	5663-5668
Journal	Tetrahedron
Volume	65
Issue number	29
DOIs	https://doi.org//10.1016/j.tet.2009.05.042
Publication status	Published - 2009

Treatment code (Nähere Zuordnung)

Basic - Fundamental (Grundlagenforschung)

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@article{2f0f2f7945714c49bde2a13158cf6c25,

title = "Investigation of Lipase-Catalyzed Michael-type Carbon-Carbon Bond Formations",

abstract = "Conjugate additions of carbon nucleophiles to appropriate acceptor molecules were investigated with respect to the synthetic potential and stereochemistry of the products. Reactions of short-chain α,β-unsaturated ketones and mono-substituted nitroalkenes with CH-acidic carboxylic ester derivatives were catalyzed by various immobilized lipases. Using methyl nitroacetate complete conversion with methyl vinyl ketone and trans-β-nitrostyrene was obtained. The reactions proceeded without enantioselectivity. Evidence for enzyme catalysis is provided by the observation that after denaturation of Candida antarctica lipase B or inhibition no reaction took place. Docking studies with the chiral addition product methyl 2-methyl-2-nitro-5-oxohexanoate did not reveal any specific binding mode for this reaction product, which would have been the requirement for stereoselective additions. These results support the experimental findings that the conjugate addition takes place without enantiopreference.",

author = "G.A. Strohmeier and T. Sovic and G. Steinkellner and Hartner, {Franz Stefan} and Aleksandra Andryushkova and T. Purkarthofer and Anton Glieder and K. Gruber and Herfried Griengl",

year = "2009",

doi = "/10.1016/j.tet.2009.05.042",

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TY - JOUR

T1 - Investigation of Lipase-Catalyzed Michael-type Carbon-Carbon Bond Formations

AU - Strohmeier, G.A.

AU - Sovic, T.

AU - Steinkellner, G.

AU - Hartner, Franz Stefan

AU - Andryushkova, Aleksandra

AU - Purkarthofer, T.

AU - Glieder, Anton

AU - Gruber, K.

AU - Griengl, Herfried

PY - 2009

Y1 - 2009

N2 - Conjugate additions of carbon nucleophiles to appropriate acceptor molecules were investigated with respect to the synthetic potential and stereochemistry of the products. Reactions of short-chain α,β-unsaturated ketones and mono-substituted nitroalkenes with CH-acidic carboxylic ester derivatives were catalyzed by various immobilized lipases. Using methyl nitroacetate complete conversion with methyl vinyl ketone and trans-β-nitrostyrene was obtained. The reactions proceeded without enantioselectivity. Evidence for enzyme catalysis is provided by the observation that after denaturation of Candida antarctica lipase B or inhibition no reaction took place. Docking studies with the chiral addition product methyl 2-methyl-2-nitro-5-oxohexanoate did not reveal any specific binding mode for this reaction product, which would have been the requirement for stereoselective additions. These results support the experimental findings that the conjugate addition takes place without enantiopreference.

AB - Conjugate additions of carbon nucleophiles to appropriate acceptor molecules were investigated with respect to the synthetic potential and stereochemistry of the products. Reactions of short-chain α,β-unsaturated ketones and mono-substituted nitroalkenes with CH-acidic carboxylic ester derivatives were catalyzed by various immobilized lipases. Using methyl nitroacetate complete conversion with methyl vinyl ketone and trans-β-nitrostyrene was obtained. The reactions proceeded without enantioselectivity. Evidence for enzyme catalysis is provided by the observation that after denaturation of Candida antarctica lipase B or inhibition no reaction took place. Docking studies with the chiral addition product methyl 2-methyl-2-nitro-5-oxohexanoate did not reveal any specific binding mode for this reaction product, which would have been the requirement for stereoselective additions. These results support the experimental findings that the conjugate addition takes place without enantiopreference.

U2 - /10.1016/j.tet.2009.05.042

DO - /10.1016/j.tet.2009.05.042

M3 - Article

VL - 65

SP - 5663

EP - 5668

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 29

ER -