4.3 Article

Lipase-catalyzed synthesis of glucose-6-O-hexanoate in deep eutectic solvents

Journal

EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY
Volume 117, Issue 2, Pages 161-166

Publisher

WILEY-BLACKWELL
DOI: 10.1002/ejlt.201400459

Keywords

Deep eutectic solvents; Glycolipid synthesis; Lipase; Transesterification

Funding

  1. BMBF [617 40003 0315928B]
  2. DFG [LU 835/6-2]
  3. Helmholtz association

Ask authors/readers for more resources

Enzymatic synthesis of sugar fatty acid esters in organic solvents is a well-described procedure to synthesize glycolipids. This study aims at replacing these solvents with deep eutectic solvents (DES), a group of solvents that gained more and more interest during the last years, since they can be easily produced from non-toxic resources. Enzymatic glycolipid synthesis in deep eutectic solvents was investigated, employing Candida antarctica lipase B (Novozyme 435) in various deep eutectic solvents. A successful lipase-catalyzed synthesis of glucose fatty acid esters gave proof of this concept, while using the two deep eutectic solvents consisting of choline chloride and urea (CC : U) and choline chloride and glucose (CC : Glc). Additionally the DES consisting of choline chloride and glucose was observed to act as solvent and substrate for the synthesis at the same time. Practical applicationsGlycolipids find applications in many everyday products like cosmetic and pharmaceutical formulations, food and classic cleaning products, utilizing their good detergent or emulsification properties. Glycolipids can, among other routes, be synthesized via lipase-catalyzed reactions, which are often carried out in organic solvents. By replacing these organic solvents with more ecologically friendly solvents like deep eutectic solvents, the reaction might be improved and the amount of waste produced could be reduced. The lipase-catalyzed synthesis of glucose-6-O-hexanoate employing glucose and vinyl hexanoate in different deep eutectic solvents was demonstrated within the manuscript.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.3
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

Article Chemistry, Multidisciplinary

Selective 1Hα NMR Methods Reveal Functionally Relevant Proline cis/trans Isomers in Intrinsically Disordered Proteins: Characterization of Minor Forms, Effects of Phosphorylation, and Occurrence in Proteome

Fanni Sebak, Peter Ecsedi, Wolfgang Bermel, Burkhard Luy, Laszlo Nyitray, Andrea Bodor

Summary: This study introduces two new NMR experiments to identify proline cis/trans isomers in proteins, detecting minor conformers present in 4-15%, and analyzes the impact of CK2 phosphorylation on the cis/trans-proline equilibrium. Statistical analysis indicates that the amino acid type also affects the distribution of cis/trans-proline.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Organic

Shift of the reaction equilibrium at high pressure in the continuous synthesis of neuraminic acid

Jannis A. Reich, Miriam Assmann, Kristin Hoelting, Paul Bubenheim, Juergen Kuballa, Andreas Liese

Summary: The importance of a compound that fights against influenza is self-evident during a pandemic. Continuous flow reactors in chemical industry are considered the next stepping stone for large scale production of these compounds. This study investigates the synthesis of N-acetylneuraminic acid in a continuous fixed-bed reactor using immobilized enzymes, and shows the potential of a high-pressure circular reactor for increasing reaction equilibrium conversion and yield.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Biochemical Research Methods

Concurrent J-evolving refocusing pulses

Sebastian Ehni, Martin R. M. Koos, Tony Reinsperger, Jens D. Haller, David L. Goodwin, Burkhard Luy

Summary: This study presents a new method to improve refocusing performance by incorporating coupling evolution into pulse design. By optimizing the refocusing pulses, heteronuclear coherence transfer in delay pulse-delay-type sequences is achieved. Additionally, efficient J-compensated refocusing pulse sandwiches are optimized.

JOURNAL OF MAGNETIC RESONANCE (2022)

Article Multidisciplinary Sciences

A chemical probe for BAG1 targets androgen receptor-positive prostate cancer through oxidative stress signaling pathway

Nane C. Kuznik, Valeria Solozobova, Irene I. Lee, Nicole Jung, Linxiao Yang, Karin Nienhaus, Emmanuel A. Ntim, Jaice T. Rottenberg, Claudia Muhle-Goll, Amrish Rajendra Kumar, Ravindra Peravali, Simone Graessle, Victor Gourain, Celia Deville, Laura Cato, Antje Neeb, Marco Dilger, Christina A. Cramer von Clausbruch, Carsten Weiss, Bruno Kieffer, G. Ulrich Nienhaus, Myles Brown, Stefan Braese, Andrew C. B. Cato

Summary: BAG1 proteins, particularly the isoform BAG1L, play crucial roles in prostate cancer by regulating the androgen receptor (AR) and affecting gene expression related to oxidative stress and metabolism. A small molecule, A4B17, targeting the BAG domain, shows promising results in downregulating AR target genes and inhibiting prostate tumor development, outperforming the clinically approved antagonist enzalutamide. BAG1 inhibitors offer unique opportunities for antagonizing AR action and prostate cancer growth.

ISCIENCE (2022)

Article Biochemistry & Molecular Biology

Cleavage of mitochondrial homeostasis regulator PGAM5 by the intramembrane protease PARL is governed by transmembrane helix dynamics and oligomeric state

Verena Siebert, Mara Silber, Elena Heuten, Claudia Muhle-Goll, Marius K. Lemberg

Summary: The intramembrane protease PARL plays a crucial role in mitochondrial protection by cleaving the mitophagy regulators PINK1 and PGAM5. The cleavage of PGAM5 is influenced by multiple hierarchical substrate features, including a membrane potential-dependent oligomeric switch.

JOURNAL OF BIOLOGICAL CHEMISTRY (2022)

Article Biochemistry & Molecular Biology

Band-selective universal 90° and 180° rotation pulses covering the aliphatic carbon chemical shift range for triple resonance experiments on 1.2 GHz spectrometers

Stella Slad, Wolfgang Bermel, Rainer Kummerle, Daniel Mathieu, Burkhard Luy

Summary: Biomolecular NMR spectroscopy requires high magnetic field strengths for high spectral resolution. This study presents band-selective universal rotation pulses with a higher ratio of selective bandwidth to maximum rf-amplitude, which perform better than standard pulses according to simulations.

JOURNAL OF BIOMOLECULAR NMR (2022)

Article Biochemistry & Molecular Biology

Pure shift amide detection in conventional and TROSY-type experiments of 13C,15N-labeled proteins

Jens D. Haller, Andrea Bodor, Burkhard Luy

Summary: We present a real-time pure shift acquisition scheme for the detection of amide protons, which can effectively suppress the full homo- and heteronuclear coupling network, leading to improved resolution and sensitivity.

JOURNAL OF BIOMOLECULAR NMR (2022)

Article Chemistry, Physical

Enhanced enzyme stability and gas utilization by microbubble aeration applying microporous aerators

Benjamin Thomas, Daniel Ohde, Simon Matthes, Paul Bubenheim, Koichi Terasaka, Michael Schlueter, Andreas Liese

Summary: During the optimization of biocatalysis processes, it is important to overcome the limitations of mass transfer and enzyme stability. Aeration with microbubbles is advantageous due to its high gas utility, low-pressure drop, and reduced foam formation. This study compares the effects of microbubble, classic sub-millibubble, and macrobubble aeration on enzyme stability and gas utility.

CATALYSIS SCIENCE & TECHNOLOGY (2023)

Article Chemistry, Physical

Photoredox Catalytic Activation of Trichlorofluoromethane and Addition to Styrenes

Desiree Steuernagel, David Rombach, Daniel Sack, Martin Koos, Burkhard Luy, Hans-Achim Wagenknecht

Summary: A new method was developed to activate CCl3F using photoredox catalysis and functionalize alkenes with the CCl2F group. N-phenylphenothiazine was used as a highly reducing organophotocatalyst. This approach combines the efficient disposal of ozone depleting substances and greenhouse gases with the synthesis of valuable organic compounds, complements the concept of atom transfer radical addition, and provides direct synthetic access to the CCl2F group as a structural motif. The broad substrate scope and multifunctionalized product class enable various subsequent transformations.

CHEMPHOTOCHEM (2023)

Article Chemistry, Organic

Cargo Encapsulation in Photochromic Supramolecular Hydrogels Depends on Specific Guest-Gelator Supramolecular Interactions

Fabian Hoffmann, Anna-Lena Leistner, Susanne Kirchner, Burkhard Luy, Claudia Muhle-Goll, Zbigniew Pianowski

Summary: This study presents a structural analysis of peptide-derived photochromic supramolecular hydrogels using advanced techniques of nuclear magnetic resonance. The hydrogels were physically loaded with a selection of biologically related compounds. The results provide detailed and correct understanding of the loading process and will guide the correct design of phototriggered drug delivery systems.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2023)

Article Chemistry, Organic

F-Tag Induced Acyl Shift in the Photochemical Cyclization of o-Alkynylated N-Alkyl-N-acylamides to Indoles

Helena Simek Tosino, Andre Jung, Olaf Fuhr, Claudia Muhle-Goll, Nicole Jung, Stefan Braese

Summary: A photochemical cyclization of F-tagged, o-alkynylated N-alkylamides to indoles catalyzed by a specific iridium complex is described. This reaction involves a rearrangement due to an electron withdrawing group, resulting in the formation of 3-acylindoles. A four-step reaction sequence including the photoreaction has been developed and optimized, leading to the synthesis of 16 derivatives with different modifications in good yields.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2023)

Review Polymer Science

Towards Sustainable Recycling of Epoxy-Based Polymers: Approaches and Challenges of Epoxy Biodegradation

Leon Klose, Neele Meyer-Heydecke, Sasipa Wongwattanarat, Jennifer Chow, Pablo Perez Garcia, Camille Carre, Wolfgang Streit, Garabed Antranikian, Ana Malvis Romero, Andreas Liese

Summary: Epoxy resins are highly valued for their properties and applications, but the challenge lies in their non-biodegradability and unsustainable recycling methods. Recent progress has been made in plastic biodegradation, but mainly focuses on other polymers, leaving epoxy underrepresented. This review examines the approaches and challenges in biodegradation and recycling of epoxy, and highlights the analytical techniques used.

POLYMERS (2023)

Article Chemistry, Physical

Polymer-Grafted 3D-Printed Material for Enzyme Immobilization-Designing a Smart Enzyme Carrier

Daniela Eixenberger, Aditya Kumar, Saskia Klinger, Nico Scharnagl, Ayad W. H. Dawood, Andreas Liese

Summary: The flow properties of packed bed reactors can be enhanced using 3D printing to create optimized structures that improve mass transfer and catalyst conversion rates. Surface-induced polymerization can increase the number of enzymes and enable smart reaction control. This publication demonstrates the application of surface-induced polymerization on 3D-printed structures for enzyme carriers.

CATALYSTS (2023)

Article Biochemistry & Molecular Biology

Enzyme-Assisted Extraction of Ulvan from the Green Macroalgae Ulva fenestrata

Ana Malvis Romero, Jose Julian Morales, Leon Klose, Andreas Liese

Summary: Ulvan is a sulfated polysaccharide extracted from green macroalgae with unique properties. This study investigates the potential of Ulva fenestrata as a source of ulvan and explores the effect of extraction methods and time on ulvan yield. Results show that longer extraction times and the combination of enzymatic and ultrasound-assisted extraction can increase the ulvan yield.

MOLECULES (2023)

No Data Available