Direct Conversion of Hydrazones to Amines using Transaminases

Carter, Eve M.; Subrizi, Fabiana; Ward, John M.; Sheppard, Tom D.; Hailes, Helen C.

doi:10.1002/cctc.202101008

Cited by 4 publications

(2 citation statements)

References 28 publications

(62 reference statements)

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“…Other synthetic pathways starting from more complex substrates and/or using multistep reactions, were also reported. [175][176][177][178] Since furfuryl amine is a commercially available product herein it is reported only a brief overview of the most promising new synthetic approaches of this bio-based molecule (yield > 70%).…”

Section: 11 †)mentioning

confidence: 99%

Beyond 2,5-furandicarboxylic acid: status quo, environmental assessment, and blind spots of furanic monomers for bio-based polymers

Annatelli,

Sánchez-Velandia,

Mazzi

et al. 2024

Green Chem.

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Section: 11 †)mentioning

confidence: 99%

Beyond 2,5-furandicarboxylic acid: status quo, environmental assessment, and blind spots of furanic monomers for bio-based polymers

Annatelli,

Sánchez-Velandia,

Mazzi

et al. 2024

Green Chem.

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“…Besides, AMHMF and AMFCA were isolated with 54% and 31% yields, respectively. Besides aldehydes and ketones, hydrazones as the amine acceptors could be converted to amines by ω-TAs in the presence of excessive amine donor . In addition, the amine yields were greatly improved in the presence of additives including PLP and poly(ethylene glycol) aldehydes, as they can sequester the hydrazine released in the reaction.…”

Section: Catalytic Formation Of the C–n Bondmentioning

confidence: 99%

(Chemo)biocatalytic Upgrading of Biobased Furanic Platforms to Chemicals, Fuels, and Materials: A Comprehensive Review

Zong

2022

ACS Catal.

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Biobased furans, such as furfural, 5-hydroxymethylfurfural, and 2,5-furandicarboxylic acid, are recognized as the top-value platform chemicals in the valorization of biomass to chemicals, fuels, and materials. Biocatalysis has emerged as a promising technique in the chemical and pharmaceutical industries because of exquisite selectivity, mild reaction conditions, environmental friendliness, etc. In this comprehensive review, we summarize the recent advances in (chemo)biocatalytic conversion of biobased furans, based on the reaction types including oxidation, reduction, C–C and C–N bonds formation, esterification, and amidation. Particularly, the biocatalysts and their catalytic mechanisms/pathways are critically discussed to allow the rational design and construction of efficient enzymes/multienzyme systems/chemobiocatalytic systems. Besides, various biocatalyst engineering and reaction engineering strategies are highlighted to intensify the processes. Future research directions are proposed to expand the chemical space of furans as well as to improve the commercial acceptance of biocatalytic processes.

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Biotransamination of Furan‐Based Aldehydes with Isopropylamine: Enzyme Screening and pH Influence

Pintor,

Cascelli,

Volkov

et al. 2023

ChemBioChem

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Furan‐based amines are highly valuable compounds which can be directly obtained via reductive amination from easily accessible furfural, 5‐(hydroxymethyl)furfural (HMF) and 2,5‐diformylfuran (DFF). Herein the biocatalytic amination of these carbonyl derivatives is disclosed using amine transaminases (ATAs) and isopropylamine (IPA) as amine donor. Among the different biocatalysts tested, the ones from Chromobacterium violaceum (Cv‐TA), Arthrobacter citreus (ArS‐TA), and variants from Arthrobacter sp. (ArRmut11‐TA) and Vibrio fluvialis (Vf‐mut‐TA), afforded high levels of product formation (>80%) at 100‐200 mM aldehyde concentration. The transformations were studied in terms of enzyme and IPA loading. The pH influence was found as a key factor and attributed to the imine/aldehyde equilibrium that can arise from the high reactivity of the carbonyl substrates with a nucleophilic amine such as IPA.

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Direct Conversion of Hydrazones to Amines using Transaminases

Abstract: This publication is part of a joint Special Collection with ChemBioChem on "BioTrans 2021". Please see our homepage for more articles in the collection.

Cited by 4 publications

References 28 publications

Beyond 2,5-furandicarboxylic acid: status quo, environmental assessment, and blind spots of furanic monomers for bio-based polymers

Beyond 2,5-furandicarboxylic acid: status quo, environmental assessment, and blind spots of furanic monomers for bio-based polymers

(Chemo)biocatalytic Upgrading of Biobased Furanic Platforms to Chemicals, Fuels, and Materials: A Comprehensive Review

Biotransamination of Furan‐Based Aldehydes with Isopropylamine: Enzyme Screening and pH Influence

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