ChemInform Abstract: ENZYME-CATALYZED ORGANIC SYNTHESIS: REGENERATION OF DEUTERATED NICOTINAMIDE COFACTORS FOR USE IN LARGE-SCALE ENZYMATIC SYNTHESIS OF DEUTERATED SUBSTANCES

Amino acids are obtained by bacterial fermentation, extraction from natural protein or enzymatic synthesis from specific substrates. With the introduction of recombinant DNA technology, it has become possible to apply more rational approaches to enzymatic synthesis of amino acids. Aspartase (L-aspartate ammonia-lyase) catalyzes the reversible deamination of L-aspartic acid to yield fumaric acid and ammonia. It is one of the most important industrial enzymes used to produce L-aspartic acid on a large scale. Here we described a novel method for [15N] L-aspartic synthesis from fumarate and ammonia (15NH4Cl) using a recombinant aspartase.

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Large-scale enzymatic synthesis of glycerol 1-phosphate

Enzyme and Microbial Technology ◽

10.1016/0141-0229(91)90183-b ◽

1991 ◽

Vol 13 (1) ◽

pp. 19-23 ◽

Cited By ~ 14

Author(s):

A. Pradines ◽

A. Klaebe ◽

J. Perie ◽

F. Paul ◽

P. Monsan

Keyword(s):

Enzymatic Synthesis ◽

Large Scale

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Synthesis of (Z)-Cinnamate Derivatives via Visible-Light-Driven E-to-Z Isomerization

SynOpen ◽

10.1055/s-0039-1690331 ◽

2019 ◽

Vol 03 (04) ◽

pp. 103-107 ◽

Cited By ~ 3

Author(s):

Penghua Shu ◽

Haichang Xu ◽

Lingxiang Zhang ◽

Junping Li ◽

Hao Liu ◽

...

Keyword(s):

Visible Light ◽

Organic Synthesis ◽

Blue Light ◽

Large Scale ◽

Practical Approach ◽

Efficient Synthesis ◽

Synthetic Methodology ◽

Visible Light Driven ◽

Large Scale Synthesis

(Z)-Cinnamate derivatives are prevalent in natural bioactive products and in organic synthesis. Herein, we report a practical approach toward the efficient synthesis of (Z)-cinnamate derivatives via visible-light-driven isomerization. When E-isomers of cinnamate derivatives were irradiated with blue light in the presence of 1 mol% Ir2(ppy)4Cl2 (ppy = 2-phenylpyridine), Z-isomers were readily obtained in good yields. This strategy allows the large-scale synthesis of (Z)-cinnamate derivatives with simple purification. This convenient, mild, and green synthetic methodology was subsequently applied to the synthesis of coumarins.

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Anodic Oxidation as an Enabling Tool for the Synthesis of Natural Products

Synthesis ◽

10.1055/s-0040-1707154 ◽

2020 ◽

Vol 52 (19) ◽

pp. 2781-2794

Author(s):

Till Opatz ◽

Leander Geske ◽

Eisuke Sato

Keyword(s):

Organic Synthesis ◽

Large Scale ◽

Bond Formation ◽

Short Review ◽

Natural Product Synthesis ◽

Environmentally Benign ◽

Full Potential ◽

Future Prospects ◽

Reaction Conditions ◽

Chemical Oxidants

Electrochemistry provides a valuable toolbox for organic synthesis and offers an appealing, environmentally benign alternative to the use of stoichiometric quantities of chemical oxidants or reductants. Its potential to control current efficiency along with providing alternative reaction conditions in a classical sense makes electrochemistry a suitable method for large-scale industrial transformations as well as for laboratory applications in the synthesis of complex molecular architectures. Even though research in this field has intensified over the recent decades, many synthetic chemists still hesitate to add electroorganic reactions to their standard repertoire, and hence, the full potential of preparative organic electrochemistry has not yet been unleashed. This short review highlights the versatility of anodic transformations by summarizing their application in natural product synthesis.1 Introduction2 Shono-Type Oxidation3 C–N/N–N Bond Formation4 Aryl–Alkene/Aryl–Aryl Coupling5 Cycloadditions Triggered by Oxidation of Electron-Rich Arenes6 Spirocycles7 Miscellaneous Transformations8 Future Prospects

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Use of enzymes as catalysts to promote key transformations in organic synthesis

Philosophical Transactions of the Royal Society of London Series B Biological Sciences ◽

10.1098/rstb.1989.0069 ◽

1989 ◽

Vol 324 (1224) ◽

pp. 577-587 ◽

Cited By ~ 24

Keyword(s):

Organic Synthesis ◽

Large Scale ◽

Immobilized Enzymes ◽

Building Blocks ◽

Optically Active ◽

The Past ◽

Small Proteins ◽

Areas Of Interest ◽

Oxidation Of Benzene ◽

Reduction Of Ketones

The field of biotransformations has developed rapidly over the past eight years. The use of esterases and lipases is now widespread; these enzymes are of particular importance in the production of optically active building blocks for organic synthesis as well as in large-scale processes involving the transesterification of fats. The latter area (i.e. the catalysis of esterification processes) has stimulated research into the properties of immobilized enzymes and the use of enzymes in low-water systems. In related work, enzymes have been used for the preparation of peptides and small proteins. Redox enzymes have been investigated extensively, particularly with regard to the stereocontrolled reduction of ketones to secondary alcohols. The methods for using commercially available enzymes of this type have become increasingly ‘userfriendly’. The controlled oxidation of hydrocarbon units is another area that has deserved increased attention. For example, oxidation of benzene and simple derivatives by Pseudomonas sp. has been researched by a number of U.K. groups. These recent advances in enzyme-catalysed reactions (using both whole-cell systems and partly purified protein) for the transformation of unnatural substrates is discussed and some areas of interest for the future are outlined.

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