Formation of CC Bonds: Enzymatic Synthesis of Cyanohydrins

Fechter, Martin; Griengl, Herfried

doi:10.1002/9783527618262.ch14b

Cited by 23 publications

(2 citation statements)

References 122 publications

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“…Even though current information on the chemical reactions is dominant, there are remarkable data on the biochemistry and other features of these valuable biocatalysts. Previous major reviews have summarized the potential of methods and reactions for synthesis of the cyanohydrins, which are valuable intermediates in follow-up synthesis of pharmaceuticals, agrochemicals, and other chemicals. − It seems there are some missing areas of HNLs, including reviews on updated biochemistry, discovery, and engineering features. Although there are robust HNLs at the present time, there is still a demand for improved reaction conditions, new chemicals, and new reactions that might be catalyzed by these enzymes.…”

Section: Introductionmentioning

confidence: 99%

Hydroxynitrile Lyases: Insights into Biochemistry, Discovery, and Engineering

2011

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Hydroxynitrile lyases are valuable enzymes for asymmetric synthesis of cyanohydrins. These hydroxyl and nitrileÀcontaining compounds are being used in production of very useful pharmaceuticals, agrochemicals, and other biologically active compounds using chemical or chemoenzymatic follow-up reactions in industry. Although a huge amount of information exists on the reaction parameters of these enzymes, including stability to pH and organic solvents, yield, reaction time, and valuable data on the enantiopurity of their products, cyanohydrins, there is a lack of update on the biochemistry, discovery, and engineering of the HNLs. Therefore, in the Introduction, we will have a look into these enzymes, cyanohydrins, and aldoxime-nitrile pathways. A brief view of functional groups and several examples of cyanohydrin-based chemicals and pharmaceuticals will also be described. Then we will present characteristics of many S-and R-selective HNLs with comparative tables for several enzymatic properties under biochemistry section. The methods of screening and discovery of these enzymes both from nature and a library of mutants will be described as well as their potential in the synthesis of chemicals. Cloning and expression of new HNLs will also be described under the discovery section. A pool of successful applications of protein engineering methods and the subsequent improvement in the properties of mutant HNLs will be reviewed in detail afterward.

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Section: Introductionmentioning

confidence: 99%

Hydroxynitrile Lyases: Insights into Biochemistry, Discovery, and Engineering

2011

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“…By using a two-phase system of water and methyl tert -butyl ether (MTBE), the equilibria can be directed to the side of the cyanohydrins . In the case of semialdehyde 5 , the chemoenzymatic HCN addition provided, on a small scale after extensive optimization, both cyanohydrins in excellent yields and 95% ee using an ( S )-selective HNL from Hevea brasiliensis ( Hb HNL) and an ( R )-selective HNL from Prunus amygdalus ( Pa HNL, Scheme ).…”

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confidence: 99%

N,N-Acetals as N-Acyliminium Ion Precursors: Synthesis and Absolute Stereochemistry of Epiquinamide

et al. 2008

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A stereoselective synthesis of (+)-epiquinamide is presented in combination with determination of the absolute configuration of the natural product. Key steps in the sequence involved chemoenzymatic formation of an enantiomerically pure cyanohydrin, reductive cyclization to the corresponding cyclic N,N-acetal, and subsequent conversion into a suitable N-acyliminium ion precursor to enable construction of the second ring.

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Enzymatic C‐C Bond Formation, Asymmetric

Kara¹,

Liese²

2010

Encyclopedia of Industrial Biotechnology

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The environmental awareness has grown during the past years focusing on efficient utilization of energy, elimination of waste and avoidance of toxic and/or hazardous reagents.Biocatalysis fulfills the requirement of “green chemistry”; since enzymes are biodegradable catalysts which can effectively catalyze the reactions under mild conditions(ambient temperature, no need for high pressure, no extreme pH, no toxic solvents and no heavy metal catalysts).C–C bond formation reactions are fundamental to all of organic chemistry, and enzymes show promise for use in this field. A variety of versatile building blocks in organic and pharmaceutical chemistry can be synthesized by biocatalysts. In comparison to available chemical routes enzymes also provide chemo‐, regio‐, and stereoselective catalysis. Different enzyme classes are applied in the field of C–C bond formation to synthesize complex, aldol reactions, and cyanohydrin formations. Few applications are also found in ketol‐ and aldol transfer reactions. Furthermore, promiscuous activity of lipases can be applied in C–C bond formation reactions.

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Formation of CC Bonds: Enzymatic Synthesis of Cyanohydrins

Cited by 23 publications

References 122 publications

Hydroxynitrile Lyases: Insights into Biochemistry, Discovery, and Engineering

Hydroxynitrile Lyases: Insights into Biochemistry, Discovery, and Engineering

N,N-Acetals as N-Acyliminium Ion Precursors: Synthesis and Absolute Stereochemistry of Epiquinamide

Enzymatic C‐C Bond Formation, Asymmetric

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