Economic kilogram-scale synthesis of the novel antiepileptic drug brivaracetam utilizing porcine pancreatic lipase

Wang, Zhen; Ke, Chunlong; Liu, Junfeng

doi:10.1039/d2re00524g

Cited by 1 publication

(1 citation statement)

References 25 publications

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“…[10,11] As an environmentally friendly synthetic route, bio-catalysis has been recognized as efficient tool for the development of chemo-and stereoselective processes over the past few decades. [12][13][14][15][16] Currently, many enzymes such as alcohol dehydrogenase, [17,18] transaminase, [19] lipase, [20,21] oxygenase, [22] lyases, [23] and oxidoreductase [24] have been widely used in the synthesis of drug intermediates. [25][26][27] Alcohol dehydrogenase (ADH), as an important biocatalyst for the reduction of carbonyl compounds, has various potential applications in chiral alcohol preparation, such as (R or S)-3'-hydroxyphenylmethylcarbinol, an intermediate of Alzheimer's drug rivastigmine.…”

Section: Introductionmentioning

confidence: 99%

Co‐Immobilization of ADH and GDH on Metal–Organic‐Framework: An Effective Biocatalyst for Asymmetric Reduction of Ketones

Ran,

Lin,

et al. 2024

ChemBioChem

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Chiral alcohols are not only important building blocks of various bioactive natural compounds and pharmaceuticals, but can serve as synthetic precursors for other valuable organic chemicals, thus the synthesis of these products is of great importance. Bio‐catalysis represents one effective way to obtain these molecules, however, the weak stability and high cost of enzymes often hinder its broad application. In this work, we designed a biological nanoreactor by embedding alcohol dehydrogenase (ADH) and glucose dehydrogenase (GDH) in metal‐organic‐framework ZIF‐8. The biocatalyst ADH&GDH@ZIF‐8 could be applied to the asymmetric reduction of a series of ketones to give chiral alcohols in high yields (up to 99%) and with excellent enantioselectivities (>99%). In addition, the heterogeneous biocatalyst could be recycled and reused at least four times with slight activity decline. Moreover, E. coli containing ADH and GDH was immobilized by ZIF‐8 to form biocatalyst E. coli@ZIF‐8, which also exhibits good catalytic behaviours. Finally, the chiral alcohols are further converted to marketed drugs (R)‐Fendiline, (S)‐Rivastigmine and NPS R‐568 respectively.

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Section: Introductionmentioning

confidence: 99%

Co‐Immobilization of ADH and GDH on Metal–Organic‐Framework: An Effective Biocatalyst for Asymmetric Reduction of Ketones

Ran,

Lin,

et al. 2024

ChemBioChem

View full text Add to dashboard Cite

show abstract

Economic kilogram-scale synthesis of the novel antiepileptic drug brivaracetam utilizing porcine pancreatic lipase

Abstract: A facile synthesis of brivaracetam, a mainstream antiepileptic drug, is described employing direct de-esterification, enzymatic hydrolysis by porcine pancreatic lipase, and cyano hydrolysis-cyclization cascade as key steps. The concise process...

Cited by 1 publication

References 25 publications

Co‐Immobilization of ADH and GDH on Metal–Organic‐Framework: An Effective Biocatalyst for Asymmetric Reduction of Ketones

Co‐Immobilization of ADH and GDH on Metal–Organic‐Framework: An Effective Biocatalyst for Asymmetric Reduction of Ketones

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