Biocatalytic Asymmetric Oxidations in Stereoselective Synthesis

Schallmey, Anett; Marı́a, Pablo Domı́nguez de; Bracco, Paula A.

doi:10.1002/9781118596784.ssd036

Cited by 5 publications

(6 citation statements)

References 123 publications

(132 reference statements)

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“…There are also Green chemistry approaches for Baeyer−Villiger oxidations based on enzyme-mediated processes, which are used for the preparation of chiral lactones. This type of biocatalysis is useful in synthetic chemistry and either isolated enzymes or living whole cells are applied for the oxidative production of valuable intermediates [ 264 – 269 ].…”

Section: Reviewmentioning

confidence: 99%

Rearrangements of organic peroxides and related processes

Yaremenko¹,

Vil²,

Demchuk³

et al. 2016

Beilstein J. Org. Chem.

194

136

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SummaryThis review is the first to collate and summarize main data on named and unnamed rearrangement reactions of peroxides. It should be noted, that in the chemistry of peroxides two types of processes are considered under the term rearrangements. These are conventional rearrangements occurring with the retention of the molecular weight and transformations of one of the peroxide moieties after O–O-bond cleavage. Detailed information about the Baeyer−Villiger, Criegee, Hock, Kornblum−DeLaMare, Dakin, Elbs, Schenck, Smith, Wieland, and Story reactions is given. Unnamed rearrangements of organic peroxides and related processes are also analyzed. The rearrangements and related processes of important natural and synthetic peroxides are discussed separately.

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Section: Reviewmentioning

confidence: 99%

Rearrangements of organic peroxides and related processes

Yaremenko¹,

Vil²,

Demchuk³

et al. 2016

Beilstein J. Org. Chem.

194

136

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“…5 Whole cell systems are therefore typically employed when numerous enzymes in multi-step reactions are required and an engineered host cell can offer advantages or when enzyme production and isolation is difficult and costly. 5,[86][87][88]…”

Section: Microbial Productionmentioning

confidence: 99%

“…In addition, the formation of inhibitory metabolites and environmental stresses can lead to lower biomass yields . Whole cell systems are therefore typically employed when numerous enzymes in multi-step reactions are required and an engineered host cell can offer advantages or when enzyme production and isolation are difficult and costly. ,− …”

Section: Biochemical Synthesismentioning

confidence: 99%

Synthesis of N-Acetyllactosamine and N-Acetyllactosamine-Based Bioactives

Alavijeh

Meyer

Gras

et al. 2021

J. Agric. Food Chem.

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N-Acetyllactosamine (LacNAc), or more specifically β-D-galactopyranosyl-1,4-N-acetyl-Dglucosamine, is a unique acyl-amino sugar and a key structural unit in human milk oligosaccharides, an antigen component of many glycoproteins and an antiviral active component for the development of effective drugs against viruses. LacNAc is useful itself and as a basic building block for producing various bioactive oligosaccharides, notably because this synthesis may be used to add value to dairy lactose. Despite a significant amount of information in the literature on the benefits, structures and types of different LacNAc-derived oligosaccharides, knowledge about their effective synthesis for large scale production is still in its infancy. This work provides a comprehensive analysis of existing production strategies of LacNAc and important LacNAc-based structures, including sialylated LacNAc, as well as poly-and oligo-LacNAc. We conclude that direct extraction from milk is too complex, while chemical synthesis is also impractical at an industrial scale. Microbial routes have application when multiple step reactions are needed but the major route to large scale biochemical production will likely lie with enzymatic routes, particularly those using β-galactosidases (for LacNAc synthesis), sialidases (for sialylated LacNAc synthesis) and β-N-acetylhexosaminidases (for oligo-LacNAc synthesis).Glycosyltransferases, especially for the biosynthesis of extended complex LacNAc structures, could also play a major role in the future. In these cases, immobilization of the enzyme can increase stability and reduce cost. Processing parameters, such as substrate concentration and purity, acceptor to donor ratio, water activity and temperature can affect product selectivity and yield.More work is needed to optimize these reaction parameters and in the development of robust, thermally stable enzymes to facilitate commercial production of these important bioactive substances. Abbreviations: 39 β3GalT β1-3 galactosyltransferase β4GalT β1-4 galactosyltransferase CMP-NeuNAc cytidine-5'-monophosphate-5-N-acetylneuraminic acid DS'LNT α2-6-linked disialyllacto-N-tetraose DSLNnT α2-6-linked disialyllacto-N-neotetraose EPEC enteropathogenic Escherichia coli GalNAc N-acetylgalactosamine GfCoV Guinea fowl coronavirus GlcNAc N-acetylglucosamine GLP-1 glucagon-like peptide 1 HEp-2 human epithelial type 2 cells iGnT β1-3 N-acetylglucosaminyltransferase IGnT β1-6 N-acetylglucosaminyltransferase iLNO iso-Lacto-N-octaose LacNAc N-acetyllactosamine LacNAc-ITag imidazolium-tagged LacNAc LacY β-galactoside permease lacZ β-galactosidase gene lgtA β1-3 N-acetylglucosaminyltransferase gene lgtB β1-4 galactosyltransferase gene LND Lacto-N-decaose LNH Lacto-N-hexaose LNnD Lacto-N-neo-decaose LNnH Lacto-N-neo-hexaose LNnO Lacto-N-neo-octaose LNnT Lacto-N-neotetraose LNO Lacto-N-octaose LNT Lacto-N-tetraose ManNAc N-acetylmannosamine MERS-CoV Middle East respiratory syndrome coronavirus Neu5Ac N-acetylneuraminic acid oNPG ortho-nitrophenyl-β-galactoside pLNH para-Lacto-N...

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“…[11][12][13] However, slow conversion rates have been reported, and the generation of side products can be a problem in whole-cell biocatalysis. [14] Moreover, downstream processes to obtain the purified l-PA can be more challenging in whole-cell biocatalysis. [15] We have previously reported two multi-enzymatic cascades that were successfully designed for the synthesis of l-PA with purified enzymes.…”

Section: Introductionmentioning

confidence: 99%

Biocatalytic Synthesis of l‐Pipecolic Acid by a Lysine Cyclodeaminase: Batch and Flow Reactors

Stalder,

Benítez‐Mateos,

Paradisi

2024

ChemCatChem

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L‐Pipecolic Acid (L‐PA) is a valuable building block for the synthesis of pharmaceuticals such as anesthetics and immunosuppressants. Thus, more efficient and greener strategies are desired for its production. Herein, we have applied a previously engineered variant of the Lysine Cyclodeaminase from Streptomyces pristinaespiralis (e‐SpLCD) for the bioconversion of L‐Lysine into L‐PA. The reaction can be performed by the free e‐SpLCD reaching full conversion to 50 mM L‐PA. From a biotechnological perspective, the process scale‐up has been trialed in a SpinChem® reactor, albeit with lower conversion yields. To further enhance the biocatalyst stability, we present a detailed study of the e‐SpLCD immobilization on microparticles. This enabled the integration of the immobilized biocatalyst into a packed‐bed reactor for the continuous flow synthesis of L‐PA. The full conversion was achieved in 90 min, maintaining also high operational stability. Remarkably, the addition of exogenous cofactor was not needed for the flow reaction, although the long‐term operational stability was improved by the addition of NAD+.

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Biocatalytic Asymmetric Oxidations in Stereoselective Synthesis

Cited by 5 publications

References 123 publications

Rearrangements of organic peroxides and related processes

Rearrangements of organic peroxides and related processes

Synthesis of N-Acetyllactosamine and N-Acetyllactosamine-Based Bioactives

Biocatalytic Synthesis of l‐Pipecolic Acid by a Lysine Cyclodeaminase: Batch and Flow Reactors

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