(De)hydratases — recent developments and future perspectives

Demming, Rebecca M.; Fischer, Mona; Schmid, Jens H.; Hauer, Bernhard

doi:10.1016/j.cbpa.2017.10.030

Cited by 41 publications

(48 citation statements)

References 40 publications

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“…In essence, these can be summarized by five consensus requirements for FAHs (Hiseni et al 2015; Demming et al 2018):A carbon-carbon double bond in cis -conformationA free carboxylate of the fatty acid substrateA chain length of at least C11 of an unsaturated fatty acid (Schmid et al 2016)A minimum distance of seven carbons between the carboxyl group and the hydrated cis -double bondAddition of a terminal OH-group is not possible (Demming et al 2017)…”

Section: Enzymes For Hydration and Their Propertiesmentioning

confidence: 99%

“…In view of its pleasant odour, ( S )-(+)-linalool displays appealing properties for the cosmetics and fragrance industries. Since it is commercially hardly available, hydration of β-myrcene was suggested as an intriguing route for ( S )-(+)-linalool production (Lüddeke and Harder 2011; Demming et al 2018), even though its industrial application has not yet been reported. In contrast, LDI is already applied for the production of industrially highly relevant dienes such as isoprene and butadiene (Marliere 2013; Botes and Conradie 2015), which are amounting to market values of billions of dollars annually (Weidenweber et al 2016).…”

Section: Enzymes For Hydration and Their Propertiesmentioning

confidence: 99%

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On the current role of hydratases in biocatalysis

Engleder

Pichler

2018

Appl Microbiol Biotechnol

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Water addition to carbon-carbon double bonds provides access to value-added products from inexpensive organic feedstock. This interesting but relatively little-studied reaction is catalysed by hydratases in a highly regio- and enantiospecific fashion with excellent atom economy. Considering that asymmetric hydration of (non-activated) carbon-carbon double bonds is virtually impossible with current organic chemistry, enzymatic hydration reactions are highly attractive for industrial applications. Hydratases have been known for several decades but their biocatalytic potential has only been explored over the past 15 years. As a result, a considerable amount of information on this enzyme group has become available, enabling their development for practical applications. This review focuses on hydratases catalysing water addition to non-activated carbon-carbon double bonds, and examines hydratases from a biochemical, structural and mechanistic angle. Current challenges and opportunities in hydration biocatalysis are discussed, and, ultimately, their potential for organic synthesis is highlighted.

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Section: Enzymes For Hydration and Their Propertiesmentioning

confidence: 99%

Section: Enzymes For Hydration and Their Propertiesmentioning

confidence: 99%

On the current role of hydratases in biocatalysis

Engleder

Pichler

2018

Appl Microbiol Biotechnol

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“…These enzymes have attracted great interest in recent years due to their high biocatalytic potential . FAHs can act on isolated carbon–carbon double bonds of the FA and produce HFAs through the reversible addition of water onto a double bond of an unsaturated FA in a regio‐ and stereospecific manner (Scheme ) . Although other enzymatic routes are present for the hydration of activated α,β‐unsaturated carbonyl compounds, FAHs can efficiently act on nonactivated carbon–carbon double bonds .…”

Section: Introductionmentioning

confidence: 99%

Rational Engineering of Hydratase from Lactobacillus acidophilus Reveals Critical Residues Directing Substrate Specificity and Regioselectivity

et al. 2019

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Enzymatic conversion of fatty acids (FAs) by fatty acid hydratases (FAHs) presents a green and efficient route for high‐value hydroxy fatty acid (HFA) production. However, limited diversity was achieved among HFAs, to date, with respect to chain length and hydroxy position. In this study, two highly similar FAHs from Lactobacillus acidophilus were compared: FA‐HY2 has a narrow substrate scope and strict regioselectivity, whereas FA‐HY1 utilizes longer chain substrates and hydrates various double‐bond positions. It is revealed that three active‐site residues play a remarkable role in directing substrate specificity and regioselectivity of hydration. If these residues on FA‐HY2 are mutated to the corresponding ones in FA‐HY1, a significant expansion of substrate scope and a distinct enhancement in hydration of double bonds towards the ω‐end of FAs is observed. A three‐residue mutant of FA‐HY2 (TM‐FA‐HY2) displayed an impressive reversal of regioselectivity towards linoleic acid, shifting the ratio of the HFA regioisomers (10‐OH/13‐OH) from 99:1 to 12:88. Notable changes in regioselectivity were also observed for arachidonic acid and for C18 polyunsaturated fatty acid substrates. In addition, TM‐FA‐HY2 converted eicosapentaenoic acid into its 12‐hydroxy product with high conversion at the preparative scale. Furthermore, it is demonstrated that microalgae are a source of diverse FAs for HFA production. This study paves the way for tailor‐made FAH design to enable the production of diverse HFAs for various applications from the polymer industry to medical fields.

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“…Die darin gesammelte und bislang weitestgehend unerforschte Sequenzdiversitäti mpliziert, dass der Einsatz von Hydratasen künftig Reaktionen ermçglichen kçnnte,d ie mit synthetischen Methoden zurzeit nicht durchführbar sind. [5,28,35,42] Gleichermaßen nicht beschrieben ist bislang die Hydratisierung eines terminalen Kohlenstoffs,d ae ine partielle positive Ladung an einem primären Kohlenstoffatom laut Markownikow-Regel nicht favorisiert wird. [36][37][38] Dieses Enzym katalysiert die regiound stereoselektive Hydratisierung von Ölsäure zur Bildung von (R)-10-Hydroxystearinsäure mit exzellentem ee (!…”

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“…Da in vergleichbaren Studien die Hydratisierung von cis-9-Undecensäure mit OhyA im zellfreien Lysat ebenfalls gering war, jedoch die Verwendung ganzer E. coli Zellen als Enzymwirt die Aktivitätd eutlich erhçhte,w urden die Biotransformationen der Ölsäurederivate analog dazu mit einem Ganzzellsystem wiederholt. [5,22,28,34,42,43] In den getesteten Reaktionsansätzen wurden lediglich die Ölsäurederivate 1b, 1h und 1j nicht umgesetzt. Charakteristische Massenfragmente in GC-MS Analysen wiesen darauf hin, dass die nichtphysiologischen Substrate 1c-1g,s owie 1i in die entsprechenden 10-Hydroxyverbindungen 2c-2g und 2i umgesetzt wurden (Abbildungen S1-S7 und S9 in den Hintergrundinformationen), während es in Kontrollreaktionen mit einem OhyA-freien E. coli Stamm weder zur Hydratisierung der Substrate, noch zu Nebenreaktionen kam (Abbildungen S1-S10).…”

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Weiterentwicklung der Substrattoleranz von Elizabethkingia meningoseptica Oleathydratase zur regio‐ und stereoselektiven Hydratisierung von Ölsäurederivaten

et al. 2019

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Die Addition von Wasser an nichtaktivierte Kohlenstoff-Kohlenstoff-Doppelbindungen von Fettsäuren wird durch Fettsäurehydratasen (FAHYs) katalysiert, und ermçglichtd ie hochselektive Oxyfunktionalisierung von erneuerbaren, çlhaltigen Rohstoffen. Da fürdie Erkennung und Bindung von Substraten die freie Carboxylatgruppe bislang als unerlässlich galt, ist der Einsatz von FAHYs gegenwärtig auf die Hydratisierung freier Fettsäuren limitiert. Diese Arbeit zeigt erstmals die Hydratisierung von Ölsäurederivaten ohne freier Carboxylatfunktion am Beispiel der Elizabethkingia meningoseptica Oleathydratase (OhyA). Im Zuge bioinformati-scherB indestudien von Substraten an die 3D-Struktur der OhyA sowie durch Aminosäuresequenzvergleiche konnten konservierte Aminosäurereste in der Substratbindetasche des Enzyms identifiziert werden. Der rationale Austausch dieser Reste führte zu Enzymvarianten mit bis zu 18-fachv erbessertem Umsatz bestimmter Ölsäurederivate ohne Beeinträchtigung der exzellenten Regio-und Stereoselektivitätd er Olefinhydratisierung.

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(De)hydratases — recent developments and future perspectives

Cited by 41 publications

References 40 publications

On the current role of hydratases in biocatalysis

On the current role of hydratases in biocatalysis

Rational Engineering of Hydratase from Lactobacillus acidophilus Reveals Critical Residues Directing Substrate Specificity and Regioselectivity

Weiterentwicklung der Substrattoleranz von Elizabethkingia meningoseptica Oleathydratase zur regio‐ und stereoselektiven Hydratisierung von Ölsäurederivaten

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