α‐Dioxygenases (α‐DOXs): Promising Biocatalysts for the Environmentally Friendly Production of Aroma Compounds

Kim, In Jung; Bayer, Thomas; Terholsen, Henrik; Bornscheuer, Uwe T.

doi:10.1002/cbic.202100693

Cited by 5 publications

(2 citation statements)

References 119 publications

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“…The α‐hydrogen of the fatty acid substrate is transferred to the tyrosyl radical, followed by O 2 radical trapping and non‐enzymatic decarboxylation of the formed α‐hydroperoxy fatty acid 185 . For more comprehensive information about α‐DOXs and its applications for fatty aldehyde synthesis, the reader is referred to a very recent review 185 . Notably, some applications target the formation of a mixture of aldehydes.…”

Section: Enzyme Catalysed Aldehyde Formationmentioning

confidence: 99%

“… 185 For more comprehensive information about α‐DOXs and its applications for fatty aldehyde synthesis, the reader is referred to a very recent review. 185 Notably, some applications target the formation of a mixture of aldehydes. In a recent example, an α‐DOX was coupled to a fatty aldehyde dehydrogenase, which lead to the iterative decarboxylation of long‐chain fatty acids to mixtures of long‐ and medium‐chain aldehydes.…”

Section: Enzyme Catalysed Aldehyde Formationmentioning

confidence: 99%

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Enzymatic reactions towards aldehydes: An overview

Schober

Dobiašová

Jurkaš

et al. 2023

Flavour & Fragrance J

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Many aldehydes are volatile compounds with distinct and characteristic olfactory properties. The aldehydic functional group is reactive and, as such, an invaluable chemical multi‐tool to make all sorts of products. Owing to the reactivity, the selective synthesis of aldehydic is a challenging task. Nature has evolved a number of enzymatic reactions to produce aldehydes, and this review provides an overview of aldehyde‐forming reactions in biological systems and beyond. Whereas some of these biotransformations are still in their infancy in terms of synthetic applicability, others are developed to an extent that allows their implementation as industrial biocatalysts.

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Section: Enzyme Catalysed Aldehyde Formationmentioning

confidence: 99%

Section: Enzyme Catalysed Aldehyde Formationmentioning

confidence: 99%

Enzymatic reactions towards aldehydes: An overview

Schober

Dobiašová

Jurkaš

et al. 2023

Flavour & Fragrance J

View full text Add to dashboard Cite

show abstract

α‐Dioxygenases (α‐DOXs): Promising Biocatalysts for the Environmentally Friendly Production of Aroma Compounds

et al. 2022

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Fatty aldehydes (FALs) can be derived from fatty acids (FAs) and related compounds and are frequently used as flavors and fragrances. Although chemical methods have been conventionally used, their selective biotechnological production aiming at more efficient and eco‐friendly synthetic routes is in demand. α‐Dioxygenases (α‐DOXs) are heme‐dependent oxidative enzymes biologically involved in the initial step of plant FA α‐oxidation during which molecular oxygen is incorporated into the Cα‐position of a FA (Cn) to generate the intermediate FA hydroperoxide, which is subsequently converted into the shortened corresponding FAL (Cn‐1). α‐DOXs are promising biocatalysts for the flavor and fragrance industries, they do not require NAD(P)H as cofactors or redox partner proteins, and they have a broad substrate scope. Here, we highlight recent advances in the biocatalytic utilization of α‐DOXs with emphasis on newly discovered cyanobacterial α‐DOXs as well as analytical methods to measure α‐DOX activity in vitro and in vivo.

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An enzymatic tandem reaction to produce odor-active fatty aldehydes

Kanter

Honold

Lüke

et al. 2022

Appl Microbiol Biotechnol

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Aldehydes represent a versatile and favored class of flavoring substances. A biocatalytic access to odor-active aldehydes was developed by conversion of fatty acids with two enzymes of the α-dioxygenase pathway. The recombinant enzymes α-dioxygenase (α-DOX) originating from Crocosphaera subtropica and fatty aldehyde dehydrogenase (FALDH) from Vibrio harveyi were heterologously expressed in E. coli, purified, and applied in a coupled (tandem) repetitive reaction. The concept was optimized in terms of number of reaction cycles and production yields. Up to five cycles and aldehyde yields of up to 26% were achieved. Afterward, the approach was applied to sea buckthorn pulp oil as raw material for the enzyme catalyzed production of flavoring/fragrance ingredients based on complex aldehyde mixtures. The most abundant fatty acids in sea buckthorn pulp oil, namely palmitic, palmitoleic, oleic, and linoleic acid, were used as substrates for further biotransformation experiments. Various aldehydes were identified, semi-quantified, and sensorially characterized by means of headspace–solid phase microextraction–gas chromatography–mass spectrometry–olfactometry (HS–SPME–GC–MS–O). Structural validation of unsaturated aldehydes in terms of double-bond positions was performed by multidimensional high-resolution mass spectrometry experiments of their Paternò–Büchi (PB) photoproducts. Retention indices and odor impressions of inter alia (Z,Z)-5,8-tetradecadienal (Z,Z)-6,9-pentadecadienal, (Z)-8-pentadecenal, (Z)-4-tridecenal, (Z)-6-pentadecenal, and (Z)-8-heptadecenal were determined for the first time. Key points • Coupled reaction of Csα-DOX and VhFALDH yields chain-shortened fatty aldehydes. • Odors of several Z-unsaturated fatty aldehydes are described for the first time. • Potential for industrial production of aldehyde-based odorants from natural sources. Graphical abstract

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α‐Dioxygenases (α‐DOXs): Promising Biocatalysts for the Environmentally Friendly Production of Aroma Compounds

Cited by 5 publications

References 119 publications

Enzymatic reactions towards aldehydes: An overview

Enzymatic reactions towards aldehydes: An overview

α‐Dioxygenases (α‐DOXs): Promising Biocatalysts for the Environmentally Friendly Production of Aroma Compounds

An enzymatic tandem reaction to produce odor-active fatty aldehydes

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