Direct Reductive Amination of Biobased Furans to <i>N</i>‐Substituted Furfurylamines by Engineered Reductive Aminase

Yang, Zhiyuan; Hao, Yacheng; Hu, Song-Qing; Zong, Min Hua; Chen, Qi; Li, Ning

doi:10.1002/adsc.202001495

Cited by 21 publications

(25 citation statements)

References 51 publications

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“…Similar to transaminase, reductive aminase also exhibited a promiscuous reaction to reduce ketones to amines and alcohols (Fig. 5B ) (González‐Martínez et al 2020a ; Yang et al 2021 ). Through reductive aminase, primary and secondary β-fluoroarylamines and fluoroarylalcohols were obtained from 5 mM fluoroarylketones (Conversions > 90%, ee = 85–99%).…”

Section: Enzymatic Synthesis Of Fluorinated Compoundsmentioning

confidence: 99%

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: 99%

Enzymatic synthesis of fluorinated compounds

Cheng

2021

Appl Microbiol Biotechnol

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“…Further engineering of AspRedAm was undertaken to unlock reductive aminations with a range of biobased furans coupled with aliphatic amines nucleophiles affording up to > 99 % conversions (Scheme 20C). [193] Mutagenesis centred on residue W210, highlighting again its importance in substrate specificity. Furfurylamines are key scaffolds in the synthesis of pharmacologically active compounds and polymers, this enzymatic route surpasses the use of toxic catalysts and chemicals.…”

Section: A Reductive Aminase From Aspergillus Oryzaementioning

confidence: 99%

“…Furthermore, as recently shown, enzymes in this family possess ketoreductase side activity. [193] Piperazine is a common building block in several pharmaceuticals such as vestipitant [200] and mirtazapine. [201] Interestingly, piperazine may also act as an amine nucleophile in reductive aminations.…”

Section: Further Ireds For Reductive Aminationmentioning

confidence: 99%

New Trends and Future Opportunities in the Enzymatic Formation of C−C, C−N, and C−O bonds

et al. 2021

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Organic chemistry provides society with fundamental products we use daily. Concerns about the impact that the chemical industry has over the environment is propelling major changes in the way we manufacture chemicals. Biocatalysis offers an alternative to other synthetic approaches as it employs enzymes, Nature's catalysts, to carry out chemical transformations. Enzymes are biodegradable, come from renewable sources, operate under mild reaction conditions, and display high selectivities in the processes they catalyse. As a highly multidisciplinary field, biocatalysis benefits from advances in different areas, and developments in the fields of molecular biology, bioinformatics, and chemical engineering have accelerated the extension of the range of available transformations (E. L. Bell et al., Nat. Rev. Meth. Prim. 2021, 1, 1-21). Recently, we surveyed advances in the expansion of the scope of biocatalysis via enzyme discovery and protein engineering (J. R. Marshall et al., Tetrahedron 2021, 82, 131926). Herein, we focus on novel enzymes currently available to the broad synthetic community for the construction of new CÀ C, CÀ N and CÀ O bonds, with the purpose of providing the non-specialist with new and alternative tools for chiral and sustainable chemical synthesis.

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“…One of the most powerful and robust methods for effective C-N bond formation of amines is the reductive amination of carbonyl compounds. [4,[18][19][20][21][22][23][24][25][26][27][28][29][30]. This transformation features compelling advantages, such as simple operating setups, mild reaction conditions, direct use of available substrates, and inexpensive reagents [31].…”

Section: Introductionmentioning

confidence: 99%