Bernhard Hauer
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View article: Channel matters: Overcoming diffusion bottlenecks via loop engineering of LinD for enhanced isoprene production
Channel matters: Overcoming diffusion bottlenecks via loop engineering of LinD for enhanced isoprene production Open
The selective chemical dehydration leading to CC double bond formation is a challenging reaction that harbors great potential for industrial applications. The cofactor independent bifunctional linalool dehydratase isomerase (LinD) from Cas…
View article: Regioselective Hydration of Terpenes with Cofactor‐Independent Carotenoid 1,2‐Hydratase
Regioselective Hydration of Terpenes with Cofactor‐Independent Carotenoid 1,2‐Hydratase Open
Terminally hydrated terpenes are highly sought‐after compounds in the flavor and fragrance industries. However, their selective synthesis remains a considerable challenge in catalysis. Regioselective hydration of non‐activated C─C double b…
View article: Regioselective Hydration of Terpenes with Cofactor‐Independent Carotenoid 1,2‐Hydratase
Regioselective Hydration of Terpenes with Cofactor‐Independent Carotenoid 1,2‐Hydratase Open
Terminally hydrated terpenes are highly sought‐after compounds in the flavor and fragrance industries. However, their selective synthesis remains a considerable challenge in catalysis. Regioselective hydration of non‐activated C─C double b…
View article: Regioselective hydration of geraniol by Escherichia coli fumarases in whole-cell biotransformations
Regioselective hydration of geraniol by Escherichia coli fumarases in whole-cell biotransformations Open
The regioselective hydration of carbon–carbon double bonds to generate alcohols is a fundamental reaction in synthetic organic chemistry, offering pathways to valuable secondary and tertiary alcohols. Biocatalysis using hydratase enzymes, …
View article: Structure‐Guided Engineering of Oleate Hydratase for the Synthesis of Small Chiral Alcohols without Decoy Molecule
Structure‐Guided Engineering of Oleate Hydratase for the Synthesis of Small Chiral Alcohols without Decoy Molecule Open
Small and chiral secondary alcohols are sought‐after compounds that are frequently used in the synthesis of biologically active compounds. However, their stereochemically correct synthesis remains a challenge for the chemical industry. Syn…
View article: Cytochrome P450 induced formation of hydroxylated polybrominated diphenyl ether and dibenzo-p-dioxin derivates from brominated phenols
Cytochrome P450 induced formation of hydroxylated polybrominated diphenyl ether and dibenzo-p-dioxin derivates from brominated phenols Open
Methoxylated polybrominated diphenyl ethers (MeO-BDEs) are a class of environmentally relevant halogenated natural products. The two most relevant isomers, 2'-MeO-BDE 68 and 6-MeO-BDE 47, were repeatedly detected at levels comparable with …
View article: Biocatalytic stereocontrolled head-to-tail cyclizations of unbiased terpenes as a tool in chemoenzymatic synthesis
Biocatalytic stereocontrolled head-to-tail cyclizations of unbiased terpenes as a tool in chemoenzymatic synthesis Open
Terpene synthesis stands at the forefront of modern synthetic chemistry and represents the state-of-the-art in the chemist’s toolbox. Notwithstanding, these endeavors are inherently tied to the current availability of natural cyclic buildi…
View article: Controlling Monoterpene Isomerization by Guiding Challenging Carbocation Rearrangement Reactions in Engineered Squalene‐Hopene Cyclases
Controlling Monoterpene Isomerization by Guiding Challenging Carbocation Rearrangement Reactions in Engineered Squalene‐Hopene Cyclases Open
The interconversion of monoterpenes is facilitated by a complex network of carbocation rearrangement pathways. Controlling these isomerization pathways is challenging when using common Brønsted and Lewis acid catalysts, which often produce…
View article: Controlling Monoterpene Isomerization by Guiding Challenging Carbocation Rearrangement Reactions in Engineered Squalene‐Hopene Cyclases
Controlling Monoterpene Isomerization by Guiding Challenging Carbocation Rearrangement Reactions in Engineered Squalene‐Hopene Cyclases Open
The interconversion of monoterpenes is facilitated by a complex network of carbocation rearrangement pathways. Controlling these isomerization pathways is challenging when using common Brønsted and Lewis acid catalysts, which often produce…
View article: Biocatalytic stereocontrolled head-to-tail cyclizations as a tool for streamlined hybrid synthesis of terpenes
Biocatalytic stereocontrolled head-to-tail cyclizations as a tool for streamlined hybrid synthesis of terpenes Open
The stereocontrolled cationic cyclization cascade is a vital step in the modular biogenesis of terpenes, as it defines the carbon skeleton's three-dimensional structure in one atom-economical step. While nature has adopted this strategy fo…
View article: Engineered cytochrome P450 for direct arylalkene-to-ketone oxidation via highly reactive carbocation intermediates
Engineered cytochrome P450 for direct arylalkene-to-ketone oxidation via highly reactive carbocation intermediates Open
Ketones are crucial intermediates in synthesis and frequent moieties in many products. The direct regioselective synthesis of ketones from internal alkenes could simplify synthetic routes and solve a long-standing challenge in catalysis. H…
View article: Biocatalytic stereocontrolled head-to-tail cyclizations as a tool for streamlined hybrid synthesis of terpenes
Biocatalytic stereocontrolled head-to-tail cyclizations as a tool for streamlined hybrid synthesis of terpenes Open
The stereocontrolled cationic cyclization cascade is a vital step in the modular biogenesis of terpenes, as it defines the carbon skeleton's three-dimensional structure in one atom-economical step. While nature has adopted this strategy fo…
View article: Cover Picture: Methylation of Unactivated Alkenes with Engineered Methyltransferases To Generate Non‐natural Terpenoids (Angew. Chem. Int. Ed. 26/2023)
Cover Picture: Methylation of Unactivated Alkenes with Engineered Methyltransferases To Generate Non‐natural Terpenoids (Angew. Chem. Int. Ed. 26/2023) Open
A methyltransferase from the green alga Chlamydomonas reinhardtii was identified and engineered for late-stage modifications of the carbon skeleton of terpenes. A variant with three changes in the amino acid sequence was able to produce me…
View article: Cover Picture: Harnessing the Structure and Dynamics of the Squalene‐Hopene Cyclase for (−)‐Ambroxide Production (Angew. Chem. Int. Ed. 22/2023)
Cover Picture: Harnessing the Structure and Dynamics of the Squalene‐Hopene Cyclase for (−)‐Ambroxide Production (Angew. Chem. Int. Ed. 22/2023) Open
Ambergris is a highly valued natural product in the fragrance industry and is also known as "floating gold" because of its biosynthesis in the intestines of sperm whales. Owing to this scarce natural resource, the stereoselective synthesis…
View article: Methylation of Unactivated Alkenes with Engineered Methyltransferases To Generate Non‐natural Terpenoids
Methylation of Unactivated Alkenes with Engineered Methyltransferases To Generate Non‐natural Terpenoids Open
Terpenoids are built from isoprene building blocks and have numerous biological functions. Selective late‐stage modification of their carbon scaffold has the potential to optimize or transform their biological activities. However, the synt…
View article: Alternative Active Site Confinement in Squalene–Hopene Cyclase Enforces Substrate Preorganization for Cyclization
Alternative Active Site Confinement in Squalene–Hopene Cyclase Enforces Substrate Preorganization for Cyclization Open
Confinement of an enzyme's active site is critical to the efficiency of chemical reactions and has been recognized as an important tool for catalysis to accelerate reactions by proximity and via specific interactions with the substrate to …
View article: Harnessing the Structure and Dynamics of the Squalene‐Hopene Cyclase for (−)‐Ambroxide Production**
Harnessing the Structure and Dynamics of the Squalene‐Hopene Cyclase for (−)‐Ambroxide Production** Open
Terpene cyclases offer enormous synthetic potential, given their unique ability to forge complex hydrocarbon scaffolds from achiral precursors within a single cationic rearrangement cascade. Harnessing their synthetic power, however, has p…
View article: Enhanced Semi‐Preparative Biotransformation of Cumene Dioxygenase: From Analytical Scale to Product Isolation
Enhanced Semi‐Preparative Biotransformation of Cumene Dioxygenase: From Analytical Scale to Product Isolation Open
Scale‐up of oxygenase catalyzed reactions is often challenging due to the limited oxygen mass transfer in aqueous solutions. To overcome such limitation, we studied different scale‐up conditions using recombinant resting cells of E. coli J…
View article: Genetically engineered Pseudomonas strains capable of metabolizing ethylene glycol and its metabolic intermediates
Genetically engineered Pseudomonas strains capable of metabolizing ethylene glycol and its metabolic intermediates Open
Presented herein are genetically engineered Pseudomonas strains capable of metabolizing ethylene glycol and producing polyhydroxyalkanoates.
View article: Expanding the Cation Cage: Squalene-Hopene Cyclase-Mediated Enantioselective Semipinacol Rearrangement
Expanding the Cation Cage: Squalene-Hopene Cyclase-Mediated Enantioselective Semipinacol Rearrangement Open
Squalene-hopene cyclases (SHCs) are the biocatalytic pendant to asymmetric Brønsted-acid catalysis and thus comprise enormous synthetic potential. Nevertheless, their substrate scope is currently limited to terpenes. Herein, we present how…
View article: Regio- and stereoselective biocatalytic hydration of fatty acids from waste cooking oils en route to hydroxy fatty acids and bio-based polyesters
Regio- and stereoselective biocatalytic hydration of fatty acids from waste cooking oils en route to hydroxy fatty acids and bio-based polyesters Open
The development of biorefinery approaches is of great relevance for the sustainable production of valuable compounds. In accordance with circular economy principles, waste cooking oils (WCOs) are renewable resources and biorefinery feedsto…
View article: Tailoring the squalene-hopene cyclase for stereoconvergent and efficient cationic cyclization cascades
Tailoring the squalene-hopene cyclase for stereoconvergent and efficient cationic cyclization cascades Open
Asymmetric catalysis has witnessed paramount lessons from terpene cyclase enzymology such as the ability to control dynamic carbocations or cationic cyclization cascades. In general, these cascades are stereodivergent and thus rely on the …
View article: Spheroplasts preparation boosts the catalytic potential of a terpene cyclase
Spheroplasts preparation boosts the catalytic potential of a terpene cyclase Open
Squalene-hopene cyclases (SHCs) are a highly valuable and attractive class of membrane-bound enzymes as sustainable biotechnological tools to produce aromas and bioactive compounds at industrial scale. However, their application as whole-c…
View article: Front Cover Picture: Engineering CYP153A<sub><i>M.aq</i></sub> to Oxyfunctionalize its Inhibitor Dodecylamine Using a LC/MS Based Rapid Flow Analysis Screening (ChemCatChem 6/2022)
Front Cover Picture: Engineering CYP153A<sub><i>M.aq</i></sub> to Oxyfunctionalize its Inhibitor Dodecylamine Using a LC/MS Based Rapid Flow Analysis Screening (ChemCatChem 6/2022) Open
The Front Cover shows an alkylamine molecule about to enter an enzyme through its substrate tunnel, which is currently under construction. In their Research Article, L. R. Rapp et al. describe dodecylamine as a P450 wild-type inhibitor tha…
View article: Engineering CYP153A<sub><i>M.aq</i></sub> to Oxyfunctionalize its Inhibitor Dodecylamine Using a LC/MS Based Rapid Flow Analysis Screening
Engineering CYP153A<sub><i>M.aq</i></sub> to Oxyfunctionalize its Inhibitor Dodecylamine Using a LC/MS Based Rapid Flow Analysis Screening Open
The catalytic space of the P450 monooxygenase CYP153A M.aq was opened from a terminal (ω‐) fatty acid hydroxylase to a catalyst capable of performing ω‐hydroxylation of dodecylamine, which is a potent inhibitor for the wild‐type enzyme. A …
View article: Directed Evolution of a Ketone Synthase for Efficient and Highly Selective Functionalization of Internal Alkenes by Accessing Reactive Carbocation Intermediates
Directed Evolution of a Ketone Synthase for Efficient and Highly Selective Functionalization of Internal Alkenes by Accessing Reactive Carbocation Intermediates Open
The direct regioselective oxidation of internal alkenes to ketones could simplify synthetic routes and solve a longstanding challenge in synthesis. This reaction is of particular importance because ketones are predominant moieties in valua…
View article: Enzymatic Friedel‐Crafts Alkylation Using Squalene‐Hopene Cyclases
Enzymatic Friedel‐Crafts Alkylation Using Squalene‐Hopene Cyclases Open
The Friedel‐Crafts alkylation constitutes one of the most important reactions for the formation of carbon‐carbon bonds. Here, we report the Friedel‐Crafts alkylation using squalene‐hopene cyclases, which provides a biological alternative t…
View article: Front Cover Picture: Semi‐Rational Engineering of Toluene Dioxygenase from <i>Pseudomonas putida</i> F1 towards Oxyfunctionalization of Bicyclic Aromatics (Adv. Synth. Catal. 21/2021)
Front Cover Picture: Semi‐Rational Engineering of Toluene Dioxygenase from <i>Pseudomonas putida</i> F1 towards Oxyfunctionalization of Bicyclic Aromatics (Adv. Synth. Catal. 21/2021) Open
The front cover picture, designed and donated by WesWizzArt and painted by the Mexican artist Way (Wayra Castillo-Guerrero), illustrates the toluene dioxygenase-catalyzed conversion of aromatics. The enzyme exhibits a high affinity for mon…