Organic reaction in water. Part 2: Michael addition in water without phase transfer agents

Silva, Flavia Martins da; Gomes, Adriana Kniaseff; Jones, J. H.

doi:10.1139/cjc-77-5-6-624

Cited by 13 publications

(3 citation statements)

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“…Many variations of this important reaction for the formation of new carbon−carbon and carbon−hetero bonds have been reported to work well in water/aqueous media. − Both basic catalysis and Lewis-acid catalysis have been applied, and nucleophiles range from neutral amines, alcohols, and thiols to anionic species including carbanions. It is therefore somewhat surprising that little effort has been made to perform stereoselective conjugate additions in aqueous media.…”

Section: B Michael-type Additionmentioning

confidence: 99%

Stereoselective Organic Reactions in Water

2002

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Ulf Lindstro ¨m was born in 1971 in Malmo ¨, Sweden. He studied Chemistry and Biology at Lund University to receive his B.Sc. degree in 1996. After earning a licentiate degree in Engineering at Lund Institute of Technology in 1998, he moved to Stockholm University to complete his doctoral thesis in 2000 under the supervision of Professor Peter Somfai. His Ph.D. work mainly concerned the development of new methods of preparing optically active nitrogen heterocycles. He then moved to California and Stanford University for postdoctoral research with Professor Eric T. Kool. There he was exposed to different aspects of nucleic acid chemistry, for example, the synthesis and molecular recognition of circular DNA. He joined the Department of Bioorganic Chemistry at Lund University as Assistant Professor in the spring of 2002. His research interest, in general, is molecular recognition and reactivity in water and, in particular, the development of chiral ligands for aqueous asymmetric synthesis.

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Section: B Michael-type Additionmentioning

confidence: 99%

Stereoselective Organic Reactions in Water

2002

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“…Hydrolytic and Michael addition activities of PalB Ser 105 Ala and the PalB wild-type in aqueous solution were explored experimentally. Because Michael addition reactions can be catalyzed by weak bases, [23] a low pH value is necessary to suppress background activity. Low pH values could possibly affect the activity of PalB.…”

Section: Determination Of Enzyme Activitiesmentioning

confidence: 99%

“…Docking studies and molecular dynamics simulations revealed an increased ability of the PalB Ser 105 Ala mutant to harbor the substrates close to a catalytically competent conformation. [23] a low pH value is necessary to suppress background activity. Low pH values could possibly affect the activity of PalB.…”

Section: Introductionmentioning

confidence: 99%

Suppressed Native Hydrolytic Activity of a Lipase to Reveal Promiscuous Michael Addition Activity in Water

et al. 2009

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Suppression of the native hydrolytic activity of Pseudozyma antarctica lipase B (PalB) (formerly Candida antarctica lipase B) in water is demonstrated. By replacing the catalytic Ser 105 residue with an alanine unit, promiscuous Michael addition activity is favored. A Michael addition reaction between methyl acrylate and acetylacetone was explored as a model system. For the PalB Ser 105 Ala mutant, the hydrolytic activity was suppressed more than 1000 times and, at the same time, the Michael addition activity was increased by a factor of 100. Docking studies and molecular dynamics simulations revealed an increased ability of the PalB Ser 105 Ala mutant to harbor the substrates close to a catalytically competent conformation.

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Preparation of Alkyls, Methylenes, and Aryls

Smith

2009

Compendium of Organic Synthetic Methods

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Organic reaction in water. Part 2: Michael addition in water without phase transfer agents

Cited by 13 publications

References 0 publications

Stereoselective Organic Reactions in Water

Stereoselective Organic Reactions in Water

Suppressed Native Hydrolytic Activity of a Lipase to Reveal Promiscuous Michael Addition Activity in Water

Preparation of Alkyls, Methylenes, and Aryls

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