Chemo‐ and Stereoselective Synthesis of Fluorinated Amino Alcohols through One‐pot Reactions using Alcohol Dehydrogenases and Amine Transaminases

González‐Martínez, Daniel; Gotor, Vicente; Gotor‐Fernández, Vicente

doi:10.1002/adsc.202000798

Cited by 7 publications

(3 citation statements)

References 64 publications

(50 reference statements)

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“…d / l -Alanine (250 mM) was used as amino donors for transaminase. Similarly, methyl/trifluoromethyl diketone was also catalyzed by transaminase to fluoroamines (Figure S5 ) (González‐Martínez et al 2020b ). Although the amination of two carbonyl groups will form three products in theory, transaminase only selectively modified smaller methyl ketones in practice.…”

Section: Enzymatic Synthesis Of Fluorinated Compoundsmentioning

confidence: 97%

Enzymatic synthesis of fluorinated compounds

Cheng

2021

Appl Microbiol Biotechnol

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Fluorinated compounds are widely used in the fields of molecular imaging, pharmaceuticals, and materials. Fluorinated natural products in nature are rare, and the introduction of fluorine atoms into organic compound molecules can give these compounds new functions and make them have better performance. Therefore, the synthesis of fluorides has attracted more and more attention from biologists and chemists. Even so, achieving selective fluorination is still a huge challenge under mild conditions. In this review, the research progress of enzymatic synthesis of fluorinated compounds is summarized since 2015, including cytochrome P450 enzymes, aldolases, fluoroacetyl coenzyme A thioesterases, lipases, transaminases, reductive aminases, purine nucleoside phosphorylases, polyketide synthases, fluoroacetate dehalogenases, tyrosine phenol-lyases, glycosidases, fluorinases, and multienzyme system. Of all enzyme-catalyzed synthesis methods, the direct formation of the C-F bond by fluorinase is the most effective and promising method. The structure and catalytic mechanism of fluorinase are introduced to understand fluorobiochemistry. Furthermore, the distribution, applications, and future development trends of fluorinated compounds are also outlined. Hopefully, this review will help researchers to understand the significance of enzymatic methods for the synthesis of fluorinated compounds and find or create excellent fluoride synthase in future research. Key points • Fluorinated compounds are distributed in plants and microorganisms, and are used in imaging, medicine, materials science . • Enzyme catalysis is essential for the synthesis of fluorinated compounds . • The loop structure of fluorinase is the key to forming the C-F bond . Supplementary Information The online version contains supplementary material available at 10.1007/s00253-021-11608-0.

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Section: Enzymatic Synthesis Of Fluorinated Compoundsmentioning

confidence: 97%

Enzymatic synthesis of fluorinated compounds

Cheng

2021

Appl Microbiol Biotechnol

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“…metal-catalysts and biocatalysts), enabling the realization of a one-pot two-step procedure with one catalytic system avoiding the isolation and storage of unstable or toxic reagents. 16…”

Section: Introductionmentioning

confidence: 99%

“…metal-catalysts and biocatalysts), enabling the realization of a one-pot two-step procedure with one catalytic system avoiding the isolation and storage of unstable or toxic reagents. 16 Quinones can be synthesized in situ from hydroquinones via the oxidation process. This transformation is efficiently catalysed by fungal laccase (EC.1.10.3.2), an enzyme used for the oxidation of benzylic alcohols, amines, and polyphenols (Scheme 1B).…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic cascade reaction as a sustainable and scalable access to para-quinols

et al. 2023

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Asymmetric Synthesis of N‐Substituted 1,2‐Amino Alcohols from Simple Aldehydes and Amines by One‐Pot Sequential Enzymatic Hydroxymethylation and Asymmetric Reductive Amination

et al. 2022

Angewandte Chemie

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The chiral N-substituted 1,2-amino alcohol motif is found in many natural and synthetic bioactive compounds. In this study, enzymatic asymmetric reductive amination of α-hydroxymethyl ketones with enantiocomplementary imine reductases (IREDs) enabled the synthesis of chiral N-substituted 1,2-amino alcohols with excellent ee values (91-99 %) in moderate to high yields (41-84 %). Furthermore, a one-pot, two-step enzymatic process involving benzaldehyde lyase-catalyzed hydroxymethylation of aldehydes and subsequent asymmetric reductive amination was developed, offering an environmentally friendly and economical way to produce N-substituted 1,2-amino alcohols from readily available simple aldehydes and amines. This methodology was then applied to rapidly access a key synthetic intermediate of anti-malaria and cytotoxic tetrahydroquinoline alkaloids.

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Chemo‐ and Stereoselective Synthesis of Fluorinated Amino Alcohols through One‐pot Reactions using Alcohol Dehydrogenases and Amine Transaminases

Cited by 7 publications

References 64 publications

Enzymatic synthesis of fluorinated compounds

Enzymatic synthesis of fluorinated compounds

Chemoenzymatic cascade reaction as a sustainable and scalable access to para-quinols

Asymmetric Synthesis of N‐Substituted 1,2‐Amino Alcohols from Simple Aldehydes and Amines by One‐Pot Sequential Enzymatic Hydroxymethylation and Asymmetric Reductive Amination

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