Across the Board: Pablo Domínguez de María on the Biocatalytic Synthesis of Esters and Amides in Aqueous Media

Marı́a, Pablo Domı́nguez de

doi:10.1002/cssc.202002298

Cited by 7 publications

(8 citation statements)

References 25 publications

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“…Notably, this situation is rapidly changing through biocatalysis. [31] Acyl transferases are able to catalyze ester and amide synthesis in water by operating under kinetic control. For example, the acyl transferase from Mycobacterium smegmatis (MsAcT), [32][33][34] catalyzes the formation of flavor esters, [35] the acylation of primary amines, [36] and peracid-mediated oxidations [37] in aqueous media.…”

Section: Introductionmentioning

confidence: 99%

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Biocatalysis as Key to Sustainable Industrial Chemistry

Alcántara

Marı́a²,

Littlechild

et al. 2022

ChemSusChem

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The role and power of biocatalysis in sustainable chemistry has been continuously brought forward step by step to its present outstanding position. The problem‐solving capabilities of biocatalysis have been realized by numerous substantial achievements in biology, chemistry and engineering. Advances and breakthroughs in the life sciences and interdisciplinary cooperation with chemistry have clearly accelerated the implementation of biocatalytic synthesis in modern chemistry. Resource‐efficient biocatalytic manufacturing processes have already provided numerous benefits to sustainable chemistry as well as customer‐centric value creation in the pharmaceutical, food, flavor, fragrance, vitamin, agrochemical, polymer, specialty, and fine chemical industries. Biocatalysis can make significant contributions not only to manufacturing processes, but also to the design of completely new value‐creation chains. Biocatalysis can now be considered as a key enabling technology to implement sustainable chemistry.

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Section: Introductionmentioning

confidence: 99%

“…The synthesis of esters and amides in aqueous media is problematical owing to competing hydrolysis. Notably, this situation is rapidly changing through biocatalysis [31] . Acyl transferases are able to catalyze ester and amide synthesis in water by operating under kinetic control.…”

Section: Introductionmentioning

confidence: 99%

Biocatalysis as Key to Sustainable Industrial Chemistry

Alcántara

Marı́a²,

Littlechild

et al. 2022

ChemSusChem

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“…15 There are no broad-scope methods for ester and amide synthesis in water, but this situation is rapidly changing. 88 Acyl transferases catalyze the formation of esters and amides in water by performing the reactions under kinetically controlled conditions, as is the case with penicillin G amidase.…”

Section: ■ Expanding the Scope Of Biocatalysismentioning

confidence: 99%

“…What is sometimes called reverse hydrolysis in water has been used for more than two decades on an industrial scale in the penicillin G amidase-catalyzed synthesis of semi-synthetic β-lactam antibiotics . There are no broad-scope methods for ester and amide synthesis in water, but this situation is rapidly changing . Acyl transferases catalyze the formation of esters and amides in water by performing the reactions under kinetically controlled conditions, as is the case with penicillin G amidase.…”

Section: Expanding the Scope Of Biocatalysismentioning

confidence: 99%

Streamlining Design, Engineering, and Applications of Enzymes for Sustainable Biocatalysis

Sheldon

Brady

2021

ACS Sustainable Chem. Eng.

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In this Perspective we show how an expansion of the scope and impact of biocatalysis in industrial organic synthesis is enabled by streamlining the underpinning biocatalyst and bioprocess engineering. We begin by discussing how the underlying need for waste reduction and high (enantio)selectivities fostered the introduction of biocatalysis as a sustainable technology for the industrial synthesis of active pharmaceutical ingredients (APIs). We continue by showing how advances in molecular biology, in particular gene sequencing and protein engineering, enabled the development of more and better enzymes, thereby broadening the industrial scope of biocatalysis. Further process improvements are provided through protein engineering for enzyme immobilization and integration of enzyme production with in vivo immobilization. Finally, the use of immobilized enzymes in continuous operation (biocatalysis in flow) facilitates the sequential integration of multi-step reactions into enzymatic or chemo-enzymatic cascade processes, thus enabling the complete, cost-effective, and environmentally attractive production of APIs.

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“…A solution to these issues could be the use of promiscuous acyltransferases which increasingly attract attention because of their ability to efficiently catalyze acyl transfer in monophasic aqueous environments, thereby overcoming the need for organic solvents, harsh reaction conditions, and long reaction times. − For example, CAL-A from Pseudozyma antarctica and other enzymes of the CAL-A superfamily can be applied in bulk water for the production of biodiesel − or in complex cascade reactions for the formation of oligocaprolactone from cyclohexanol . To date, the most widely studied promiscuous acyltransferase is MsAcT from Mycobacterium smegmatis , which has been used for the formation of various esters , and amides, , including flavor compounds and high-value tryptamine derivatives .…”

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Efficient Acylation of Sugars and Oligosaccharides in Aqueous Environment Using Engineered Acyltransferases

et al. 2021

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A major challenge for the enzymatic synthesis of sugar esters is the low solubility of sugars in anhydrous, often toxic, organic solvents. We overcame this limitation by using acyltransferases for efficient acetylation of sugars in water. Selective 6-O-acetylation of glucose, maltose, and maltotriose with conversions of up to 78% was achieved within 15 min using engineered acyltransferases (4 μM). Moreover, we identified EstA as a promiscuous acyltransferase preferentially acetylating sugars instead of hydrophobic acyl acceptors. This expands the applicability of promiscuous acyltransferases to sugar modifications and contributes to the understanding of how to adapt acyltransferases to hydrophilic substrates.

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Across the Board: Pablo Domínguez de María on the Biocatalytic Synthesis of Esters and Amides in Aqueous Media

Cited by 7 publications

References 25 publications

Biocatalysis as Key to Sustainable Industrial Chemistry

Biocatalysis as Key to Sustainable Industrial Chemistry

Streamlining Design, Engineering, and Applications of Enzymes for Sustainable Biocatalysis

Efficient Acylation of Sugars and Oligosaccharides in Aqueous Environment Using Engineered Acyltransferases

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