Efficient Chemo-Enzymatic Flow Synthesis of High Value Amides and Esters

Annunziata, Francesca; Contente, Martina Letizia; Betti, Daniele; Pinna, Christian; Molinari, Francesco; Tamborini, Lucia; Pinto, Andrea

doi:10.3390/catal10080939

Cited by 20 publications

(19 citation statements)

References 31 publications

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“…It was shown that MsAcT also works well for the synthesis of esters and amides in water or in biphasic mixture of water and acyl donor in flow, and this chemistry was broadly explored (Scheme 31). [298][299][300] A single mutation of the nucleophile in the catalytic triad of MsAcT revealed even more possibilities for the application of this intriguing enzyme. By changing the catalytic triade from the standard Ser-His-Asp to Cys-His-Asp the hydroxy group of serine was replaced by the thiol of cysteine.…”

Section: Synthesis Of Esters and Amides In Watermentioning

confidence: 99%

Biocatalysis making waves in organic chemistry

2022

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Section: Synthesis Of Esters and Amides In Watermentioning

confidence: 99%

Biocatalysis making waves in organic chemistry

2022

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“…A chemoenzymatic approach for the synthesis of the blockbuster drugs procainamide (38), procaine (39) and butacaine (40) was carried out very recently by Tamborini et al (Scheme 15) [142]. Scheme 15.…”

Section: Single-step Flow Biocatalytic Systemsmentioning

confidence: 99%

“…Scheme 15. Schematic overview of the flow synthesis of procainamide (38), procaine (39) and butacaine (40) using immobilized MsAcT enzyme [142].…”

Section: Single-step Flow Biocatalytic Systemsmentioning

confidence: 99%

Flow Biocatalysis: A Challenging Alternative for the Synthesis of APIs and Natural Compounds

Santi

Sancineto

Nascimento

et al. 2021

IJMS

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Biocatalysts represent an efficient, highly selective and greener alternative to metal catalysts in both industry and academia. In the last two decades, the interest in biocatalytic transformations has increased due to an urgent need for more sustainable industrial processes that comply with the principles of green chemistry. Thanks to the recent advances in biotechnologies, protein engineering and the Nobel prize awarded concept of direct enzymatic evolution, the synthetic enzymatic toolbox has expanded significantly. In particular, the implementation of biocatalysts in continuous flow systems has attracted much attention, especially from industry. The advantages of flow chemistry enable biosynthesis to overcome well-known limitations of “classic” enzymatic catalysis, such as time-consuming work-ups and enzyme inhibition, as well as difficult scale-up and process intensifications. Moreover, continuous flow biocatalysis provides access to practical, economical and more sustainable synthetic pathways, an important aspect for the future of pharmaceutical companies if they want to compete in the market while complying with European Medicines Agency (EMA), Food and Drug Administration (FDA) and green chemistry requirements. This review focuses on the most recent advances in the use of flow biocatalysis for the synthesis of active pharmaceutical ingredients (APIs), pharmaceuticals and natural products, and the advantages and limitations are discussed.

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“…Upon solvent evaporation, the intermediates were redissolved in methanol (amide intermediate) or ethyl acetate (ester intermediate) and hydrogenated (60 • C, 1 × 10 6 Pa). Yields in excess of 99% were reported [124].…”

Section: Chemoenzymatic Reactionsmentioning

confidence: 99%

Multi-Enzyme Systems in Flow Chemistry

Fernandes

Carvalho

2021

Processes

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Recent years have witnessed a growing interest in the use of biocatalysts in flow reactors. This merging combines the high selectivity and mild operation conditions typical of biocatalysis with enhanced mass transfer and resource efficiency associated to flow chemistry. Additionally, it provides a sound environment to emulate Nature by mimicking metabolic pathways in living cells and to produce goods through the systematic organization of enzymes towards efficient cascade reactions. Moreover, by enabling the combination of enzymes from different hosts, this approach paves the way for novel pathways. The present review aims to present recent developments within the scope of flow chemistry involving multi-enzymatic cascade reactions. The types of reactors used are briefly addressed. Immobilization methodologies and strategies for the application of the immobilized biocatalysts are presented and discussed. Key aspects related to the use of whole cells in flow chemistry are presented. The combination of chemocatalysis and biocatalysis is also addressed and relevant aspects are highlighted. Challenges faced in the transition from microscale to industrial scale are presented and discussed.

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Efficient Chemo-Enzymatic Flow Synthesis of High Value Amides and Esters

Cited by 20 publications

References 31 publications

Biocatalysis making waves in organic chemistry

Biocatalysis making waves in organic chemistry

Flow Biocatalysis: A Challenging Alternative for the Synthesis of APIs and Natural Compounds

Multi-Enzyme Systems in Flow Chemistry

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