Inverting hydrolases and their use in enantioconvergent biotransformations

Schöber, Markus; Faber, Kurt

doi:10.1016/j.tibtech.2013.05.005

Cited by 48 publications

(44 citation statements)

References 102 publications

(68 reference statements)

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“…[124] Among them, Pseudomonas sp. DSM 6611 alkylsulfatase (Pisa1) has widely been used in the deracemization of sec-alcohols.…”

Section: Scheme 21mentioning

confidence: 99%

Why Leave a Job Half Done? Recent Progress in Enzymatic Deracemizations

Díaz‐Rodríguez¹,

Lavandera

Gotor³

2015

CGC

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Abstract. In recent years the usefulness of enzymatic systems to obtain a single stereoisomerically pure compound starting from a racemate has been expanded. Moreover, current advances in protein engineering, molecular biology and modeling tools are the basis to improve the catalytic properties of enzymes to face novel synthetic challenges. Also, medium engineering and novel immobilization methods of (bio)catalysts are enhancing the productivity of biocatalytic processes making them suitable for being scalable. The development of multienzymatic protocols and the combination of enzymes with other catalysts are providing a wide range of synthetic possibilities that are expanding the scope of these transformations even at industrial scale. Herein we will describe an overview of recent (chemo)enzymatic deracemizations, focusing on the strategy employed (dynamic kinetic resolution, stereoinversion, cyclic deracemization or enantioconvergent process), the type of substrate (e.g., alcohols, amines, carboxylic acid derivatives or carbonylic compounds), and the biocatalyst(s) used.

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“…[124] Among them, Pseudomonas sp. DSM 6611 alkylsulfatase (Pisa1) has widely been used in the deracemization of sec-alcohols.…”

Section: Scheme 21mentioning

confidence: 99%

Why Leave a Job Half Done? Recent Progress in Enzymatic Deracemizations

Díaz‐Rodríguez¹,

Lavandera

Gotor³

2015

CGC

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“…This limitation of chemocatalysis is presumably the reason for the niche existence of sulfate monoesters in organic synthesis. [17][18][19][20][21][22] In contrast, enzyme-catalyzed hydrolysis of sulfate monoesters using sulfatases offers a broad spectrum of various enantio-and stereocomplementary transformations. [19][20][21][22] Sulfatases are collected in a heterogenic class of enzymes, which is composed of three distinct subgroups acting through different mechanisms, i.e.…”

Section: Inverting and Retaining Sulfatasesmentioning

confidence: 99%

“…aryl-, alkyl-, and AE-ketogluturate-dependent sulfatases. [21,22] The latter group catalyzes the oxidative cleavage of (primary) sulfate esters at the expense of AE-ketoglutarate (2-oxoglutarate), yielding an aldehyde and inorganic sulfate. Because this transformation goes in hand with the destruction of a (potential) chiral center, it is of limited synthetic interest.…”

Section: Inverting and Retaining Sulfatasesmentioning

confidence: 99%

3.10 Emerging Enzymes

Glueck,

Hammer,

Hauer

et al. 2015

Biocatalysis in Organic Synthesis 3

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The broad application of enzymes in industry is still impeded by the limited repertoire of available enzymes. New applications of biocatalysts in a sustainable bio-based economy, especially for employment in bioremediation, bioenergy, and bioproducts, appear to be the driving force behind the increased prevalence of novel enzymatic catalysts. Advances in synthetic biology, enzyme engineering, de novo enzyme (re)design, exploitation of enzyme promiscuity, and DNA sequencing technologies show great potential to facilitate the development of more efficient enzymes. Combined efforts would have the following benefits: an increased range of biocatalysts with different catalytic activities would be available and more biocatalysts with improved characteristics suitable for (bio)synthetic chemistry approaches would be discovered. This chapter demonstrates the potential of enzymes that have been investigated recently, but not yet fully exploited, for applications in chemical synthesis: nitrile reductases, sulfatases, phenol-coupling monooxygenases, squalene hopene cyclases, and aldoxime dehydratases. Examples of emerging enzymes and microorganisms that have been studied over the last few years and that have acquired scientific as well as industrial interest are described to illustrate the synthetic potential of these biocatalysts.The screening reactions were run in UV star 96-well plates using recombinant His-tagged enzymes purified via nickel affinity chromatography. The following conditions were applied: nitrile reductase (45 ìM, purity >85%) in buffer [100 mM Tris, 50 mM KCl, 1.15 mM 3.10.

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“…Indeed, hydrolase-catalyzed kinetic resolution remains an attractive option, because of the simplicity of the process and the high enantioselectivity of biocatalysis under mild conditions [11].…”

Section: Introductionmentioning

confidence: 99%