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Article ; Online: Database-driven in silico-identification and characterization of novel aldoxime dehydratases.

Hinzmann, Michael / Yavuzer, Hilmi / Hinzmann, Alessa / Gröger, Harald

2023 Volume 367, Page(s) 81–88

Abstract: Aldoxime dehydratases (Oxds) are a unique class of enzymes, which catalyzes the dehydration of aldoximes to nitriles in an aqueous environment. Recently, they gained attention as a catalyst for a green and cyanide-free alternative to established nitrile ... ...

Abstract	Aldoxime dehydratases (Oxds) are a unique class of enzymes, which catalyzes the dehydration of aldoximes to nitriles in an aqueous environment. Recently, they gained attention as a catalyst for a green and cyanide-free alternative to established nitrile syntheses, which often require the use of toxic cyanides and harsh reaction conditions. Up to now only thirteen aldoxime dehydratases have been discovered and biochemically characterized. This raised the interest for identifying further Oxds with, e.g., complementary properties in terms of substrate scope. In this study, 16 novel genes, presumably encoding aldoxime dehydratases, were selected by using a commercially available 3DM database based on OxdB, an Oxd from Bacillus sp. OxB-1. Out of 16 proteins, six enzymes with aldoxime dehydratases activity were identified, which differ in their substrate scope and activity. While some novel Oxds showed better performance for aliphatic substrate such as n-octanaloxime compared to the well characterized OxdRE from Rhodococcus sp. N-771, some showed activity for aromatic aldoximes, leading to an overall high usability of these enzymes in organic chemistry. The applicability for organic synthesis was underlined by converting 100 mM n-octanaloxime at a 10 mL scale within 5 h with the novel aldoxime dehydratase OxdHR as whole-cell catalyst (33 mg
MeSH term(s)	Hydro-Lyases/genetics ; Hydro-Lyases/metabolism ; Oximes/metabolism ; Bacillus/metabolism ; Nitriles/metabolism
Chemical Substances	aldoxime dehydratase (EC 4.2.1.-) ; acetaldehyde oxime (ME6U10SD7D) ; Hydro-Lyases (EC 4.2.1.-) ; Oximes ; Nitriles
Language	English
Publishing date	2023-03-11
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	843647-2
ISSN	1873-4863 ; 0168-1656 ; 1389-0352
ISSN (online)	1873-4863
ISSN	0168-1656 ; 1389-0352
DOI	10.1016/j.jbiotec.2023.02.007
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Article ; Online: Searches for exotic new physics in CMS

Hinzmann A.

EPJ Web of Conferences, Vol 95, p

2015 Volume 04030

Abstract: An overview of the CMS search program for exotic new physics is given based on a representative set of models, experimental techniques and final states. Exotic new physics models are briefly reviewed and exotic experimental techniques are introduced ... ...

Abstract	An overview of the CMS search program for exotic new physics is given based on a representative set of models, experimental techniques and final states. Exotic new physics models are briefly reviewed and exotic experimental techniques are introduced before the experimental results based on 8 TeV pp collision data in 9 different final states are discussed.
Keywords	Science ; Q ; Physics ; QC1-999
Language	English
Publishing date	2015-01-01T00:00:00Z
Publisher	EDP Sciences
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Searches for exotic new physics in CMS

Hinzmann A.

EPJ Web of Conferences, Vol 95, p

2015 Volume 04030

Abstract	An overview of the CMS search program for exotic new physics is given based on a representative set of models, experimental techniques and final states. Exotic new physics models are briefly reviewed and exotic experimental techniques are introduced before the experimental results based on 8 TeV pp collision data in 9 different final states are discussed.
Keywords	Science ; Q ; Physics ; QC1-999
Language	English
Publishing date	2015-01-01T00:00:00Z
Publisher	EDP Sciences
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article: Selective Hydrogenation of Fatty Nitriles to Primary Fatty Amines: Catalyst Evaluation and Optimization Starting from Octanenitrile

Hinzmann, Alessa / Gröger, Harald

European journal of lipid science and technology. 2020 Jan., v. 122, no. 1

2020

Abstract: In this contribution, an evaluation of the potential of various homogeneous and heterogeneous catalysts for a selective hydrogenation of fatty nitriles toward primary amines is reported exemplified for the conversion of octanenitrile into octane‐1‐amine ... ...

Abstract	In this contribution, an evaluation of the potential of various homogeneous and heterogeneous catalysts for a selective hydrogenation of fatty nitriles toward primary amines is reported exemplified for the conversion of octanenitrile into octane‐1‐amine as a model reaction. When using heterogeneous catalysts such as the ruthenium catalyst Ru/C, the palladium catalyst Pd/C, and the platinum catalyst Pt/Al2O3, low selectivities in the hydrogenation are observed, thus leading to a large portion of secondary and tertiary amine side‐products. For example, when using Ru/C as a heterogeneous catalyst, high conversions of up to 99% are obtained but the selectivity remains low with a percentage of the primary amine being at 60% at the highest. The study further reveals a high potential of homogeneous ruthenium and manganese catalysts. When also taking into account economical considerations with respect to the metal price, in particular, manganese catalysts turn out to be attractive for the desired transformation and their application in the model reaction leads to the desired primary amine product with excellent conversion, selectivity, and high yield. Practical Applications: This work describes an optimized hydrogenation process for transforming fatty nitriles to their corresponding primary amines. In general, fatty amines belong to the most applied fatty acid‐derived compounds in the chemical industry with an annual product volume exceeding 800 000 tons per year in 2011 and are widely required in the chemical industry since such compounds are either directly used in home products such as fabric softeners, dishwashing liquids, car wash detergents, or carpet cleaners or in a broad range of industrial products, for example, lubricating additives, flotation agents, dispersants, emulsifiers, corrosion inhibitors, fungicides, and bactericides, showing additional major applications, e.g., in the detergents industry. Among them primary amines play an important industrial role. However, a major concern of current processes is the lack of selectivity and the formation of secondary and tertiary amines as side‐products. By modifying a recently developed catalytic system based on manganese as economically attractive and environmentally benign metal component an efficient and selective access to fatty amines when starting from the corresponding nitriles is achieved. For example, hydrogenation of octanenitrile leads to a synthesis of octane‐1‐amine with >99% conversion and excellent selectivity with formation of secondary and tertiary amine side‐products being suppressed to an amount of <1%.
Keywords	additives ; aluminum oxide ; antibiotics ; catalysts ; catalytic activity ; chemical industry ; cleaners ; corrosion ; detergents ; dispersants ; emulsifiers ; fabrics ; fungicides ; hydrogenation ; manganese ; nitriles ; palladium ; platinum ; prices ; primary amines ; ruthenium ; tertiary amines
Language	English
Dates of publication	2020-01
Publishing place	John Wiley & Sons, Ltd
Document type	Article
Note	JOURNAL ARTICLE
ZDB-ID	2003265-1
ISSN	1438-7697
ISSN	1438-7697
DOI	10.1002/ejlt.201900163
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Synthetic Processes toward Nitriles without the Use of Cyanide: A Biocatalytic Concept Based on Dehydration of Aldoximes in Water.

Hinzmann, Alessa / Betke, Tobias / Asano, Yasuhisa / Gröger, Harald

Chemistry (Weinheim an der Bergstrasse, Germany)

2021 Volume 27, Issue 17, Page(s) 5313–5321

Abstract: While belonging to the most fundamental functional groups, nitriles represent a class of compound that still raises challenges in terms of an efficient, cost-effective, general and, at the same time, sustainable way for their synthesis. Complementing ... ...

Abstract	While belonging to the most fundamental functional groups, nitriles represent a class of compound that still raises challenges in terms of an efficient, cost-effective, general and, at the same time, sustainable way for their synthesis. Complementing existing chemical routes, recently a cyanide-free enzymatic process technology based on the use of an aldoxime dehydratase (Oxd) as a biocatalyst component has been developed and successfully applied for the synthesis of a range of nitrile products. In these biotransformations, the Oxd enzymes catalyze the dehydration of aldoximes as readily available substrates to the nitrile products. Herein, these developments with such enzymes are summarized, with a strong focus on synthetic applications. It is demonstrated that this biocatalytic technology has the potential to "cross the bridge" between the production of fine chemicals and pharmaceuticals, on one hand, and bulk and commodity chemicals, on the other.
MeSH term(s)	Cyanides ; Dehydration ; Humans ; Nitriles ; Oximes ; Water
Chemical Substances	Cyanides ; Nitriles ; Oximes ; Water (059QF0KO0R)
Language	English
Publishing date	2021-01-22
Publishing country	Germany
Document type	Journal Article
ZDB-ID	1478547-X
ISSN	1521-3765 ; 0947-6539
ISSN (online)	1521-3765
ISSN	0947-6539
DOI	10.1002/chem.202001647
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Article ; Online: Enzymatic Synthesis of Aliphatic Nitriles at a Substrate Loading of up to 1.4 kg/L: A Biocatalytic Record Achieved with a Heme Protein.

Hinzmann, Alessa / Glinski, Sylvia / Worm, Marion / Gröger, Harald

The Journal of organic chemistry

2019 Volume 84, Issue 8, Page(s) 4867–4872

Abstract: A biocatalytic approach toward linear aliphatic nitriles being widely used as industrial bulk chemicals has been developed that runs at high substrate loadings of up to 1.4 kg/L as demonstrated for the synthesis of n-octanenitrile. This substrate loading ...

Abstract	A biocatalytic approach toward linear aliphatic nitriles being widely used as industrial bulk chemicals has been developed that runs at high substrate loadings of up to 1.4 kg/L as demonstrated for the synthesis of n-octanenitrile. This substrate loading is one of the highest ever reported in biocatalysis and to best of our knowledge the highest obtained for a water-immiscible product in aqueous medium. It is noteworthy that the biotransformation at such a high substrate loading was achieved by means of a metalloprotein bearing an iron-containing heme subunit in the active site. In detail, an aldoxime dehydratase from Bacillus sp. OxB-1 was used as a biocatalyst for a dehydration of aldoximes as readily available starting materials due to their easy preparation from aliphatic aldehydes through spontaneous condensation with hydroxylamine as bulk chemical. Excellent conversions toward the nitriles in the two-phase system were achieved and the products are easily separated from the reaction mixture without the need for further purification. Aliphatic nitriles are used in industry as solvents and intermediates for the production of surfactants and life sciences products.
MeSH term(s)	Biocatalysis ; Hemeproteins/chemistry ; Hemeproteins/metabolism ; Hydro-Lyases/chemistry ; Hydro-Lyases/metabolism ; Models, Molecular ; Molecular Structure ; Nitriles/chemistry ; Nitriles/metabolism ; Substrate Specificity
Chemical Substances	Hemeproteins ; Nitriles ; Hydro-Lyases (EC 4.2.1.-) ; aldoxime dehydratase (EC 4.2.1.-)
Language	English
Publishing date	2019-04-08
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.9b00184
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Article: Enzymatic Synthesis of Aliphatic Nitriles at a Substrate Loading of up to 1.4 kg/L: A Biocatalytic Record Achieved with a Heme Protein

Hinzmann, Alessa / Sylvia Glinski / Marion Worm / Harald Gröger

Journal of organic chemistry. 2019 Mar. 07, v. 84, no. 8

2019

Abstract	A biocatalytic approach toward linear aliphatic nitriles being widely used as industrial bulk chemicals has been developed that runs at high substrate loadings of up to 1.4 kg/L as demonstrated for the synthesis of n-octanenitrile. This substrate loading is one of the highest ever reported in biocatalysis and to best of our knowledge the highest obtained for a water-immiscible product in aqueous medium. It is noteworthy that the biotransformation at such a high substrate loading was achieved by means of a metalloprotein bearing an iron-containing heme subunit in the active site. In detail, an aldoxime dehydratase from Bacillus sp. OxB-1 was used as a biocatalyst for a dehydration of aldoximes as readily available starting materials due to their easy preparation from aliphatic aldehydes through spontaneous condensation with hydroxylamine as bulk chemical. Excellent conversions toward the nitriles in the two-phase system were achieved and the products are easily separated from the reaction mixture without the need for further purification. Aliphatic nitriles are used in industry as solvents and intermediates for the production of surfactants and life sciences products.
Keywords	Bacillus (bacteria) ; active sites ; aldehydes ; biocatalysis ; biocatalysts ; biotransformation ; chemical reactions ; enzymes ; heme ; heme proteins ; hydroxylamine ; industry ; metalloproteins ; nitriles ; organic chemistry ; solvents ; surfactants
Language	English
Dates of publication	2019-0307
Size	p. 4867-4872.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.9b00184
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Article ; Online: Effect of Particle Wettability and Particle Concentration on the Enzymatic Dehydration of n-Octanaloxime in Pickering Emulsions.

Bago Rodriguez, Ana Maria / Schober, Lukas / Hinzmann, Alessa / Gröger, Harald / Binks, Bernard P

Angewandte Chemie (International ed. in English)

2020 Volume 60, Issue 3, Page(s) 1450–1457

Abstract: Pickering emulsion systems have emerged as platforms for the synthesis of organic molecules in biphasic biocatalysis. Herein, the catalytic performance was evaluated for biotransformation using whole cells exemplified for the dehydration of n- ... ...

Abstract	Pickering emulsion systems have emerged as platforms for the synthesis of organic molecules in biphasic biocatalysis. Herein, the catalytic performance was evaluated for biotransformation using whole cells exemplified for the dehydration of n-octanaloxime to n-octanenitrile catalysed by an aldoxime dehydratase (OxdB) overexpressed in E. coli. This study was carried out in Pickering emulsions stabilised solely with silica particles of different hydrophobicity. We correlate, for the first time, the properties of the emulsions with the conversion of the reaction, thus gaining an insight into the impact of the particle wettability and particle concentration. When comparing two emulsions of different type with similar stability and droplet diameter, the oil-in-water (o/w) system displayed a higher conversion than the water-in-oil (w/o) system, despite the conversion in both cases being higher than that in a "classic" two-phase system. Furthermore, an increase in particle concentration prior to emulsification resulted in an increase of the interfacial area and hence a higher conversion.
MeSH term(s)	Biocatalysis ; Dehydration/enzymology ; Emulsions ; Humans ; Wettability
Chemical Substances	Emulsions
Language	English
Publishing date	2020-12-21
Publishing country	Germany
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2011836-3
ISSN	1521-3773 ; 1433-7851
ISSN (online)	1521-3773
ISSN	1433-7851
DOI	10.1002/anie.202013171
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Article ; Online: The structure of liquid SnTe under pressure.

Hinzmann, Andreas / Chiba, Ayano / Tsuji, Kazuhiko

Journal of physics. Condensed matter : an Institute of Physics journal

2012 Volume 24, Issue 11, Page(s) 115103

Abstract: We investigated the structure of liquid SnTe at high pressures up to 8.2 GPa by energy-dispersive x-ray diffraction. On melting at low pressures, the crystalline B1 structure changed into not B1-like but distorted-B1-like local structure. We also found ... ...

Abstract	We investigated the structure of liquid SnTe at high pressures up to 8.2 GPa by energy-dispersive x-ray diffraction. On melting at low pressures, the crystalline B1 structure changed into not B1-like but distorted-B1-like local structure. We also found that the structure changes at around 1.6-3.3 GPa. At high pressures, the bond angle and coordination number approached those for B2-based structure, but still showed clear deviations from B2-like local structure.
Language	English
Publishing date	2012-03-21
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	1472968-4
ISSN	1361-648X ; 0953-8984
ISSN (online)	1361-648X
ISSN	0953-8984
DOI	10.1088/0953-8984/24/11/115103
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Article: Combined spike-related functional MRI and multiple source analysis in the non-invasive spike localization of benign rolandic epilepsy.

Boor, R / Jacobs, J / Hinzmann, A / Bauermann, T / Scherg, M / Boor, S / Vucurevic, G / Pfleiderer, C / Kutschke, G / Stoeter, P

Clinical neurophysiology : official journal of the International Federation of Clinical Neurophysiology

2007 Volume 118, Issue 4, Page(s) 901–909

Abstract: Objective: To localize the irritative zone in children by combined spike-related fMRI and EEG multiple source analysis (MSA) in children with benign rolandic epilepsy.: Methods: Interictal spikes were averaged and localized using MSA, and source ... ...

Abstract	Objective: To localize the irritative zone in children by combined spike-related fMRI and EEG multiple source analysis (MSA) in children with benign rolandic epilepsy. Methods: Interictal spikes were averaged and localized using MSA, and source locations were displayed in the anatomical 3D-MRI in 11 patients (5-12 yrs, median 10). Interictal spikes were additionally recorded during the fMRI acquisition (EEG-fMRI), and the fMRI sequences were correlated off-line with the EEG spikes. Results: MSA revealed an initial central dipole in all patients, including the face or hand area. A second dipolar source was mostly consistent with propagated activity. BOLD activations from EEG-fMRI, consistent with the locations of the initial dipoles, were found in four patients. We found additional large areas of BOLD activations in 3 of these subjects extending into the sylvian fissure and the insula. These were identified as propagated activity by MSA using the short time differences in the source waveforms. Conclusions: MSA provided reliable localization of the spike onset zone in all children with benign rolandic epilepsy. Using the combination of EEG-fMRI and MSA we were able to discriminate the spike onset zone from propagated epileptiform source activity, using the spatial resolution of the EEG-fMRI technique and the temporal resolution of the MSA. However, the sensitivity of the EEG-fMRI technique was low and further improvements of the technique are warranted. Significance: This study shows that a combination of EEG-fMRI and MSA may be a powerful tool to describe the irritative zone of patients with idiopathic focal epilepsies. Clinical studies in patients with non-idiopathic focal epilepsies may clarify whether both techniques can be used as complementary clinical tools to localize the onset of interictal epileptic activity in focal epilepsies.
MeSH term(s)	Brain Mapping ; Cerebral Cortex/blood supply ; Cerebral Cortex/physiopathology ; Child ; Child, Preschool ; Electroencephalography ; Epilepsy, Rolandic/pathology ; Epilepsy, Rolandic/physiopathology ; Humans ; Image Processing, Computer-Assisted/methods ; Magnetic Resonance Imaging ; Oxygen/blood ; Principal Component Analysis
Chemical Substances	Oxygen (S88TT14065)
Language	English
Publishing date	2007-04
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	1463630-x
ISSN	1872-8952 ; 1388-2457 ; 0921-884X
ISSN (online)	1872-8952
ISSN	1388-2457 ; 0921-884X
DOI	10.1016/j.clinph.2006.11.272
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