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Highly efficient enantioselective liquid-liquid extraction of 1,2-amino-alcohols using SPINOL based phosphoric acid hosts

2017, Pinxterhuis, Erik B., Gualtierotti, Jean-Baptiste, Heeres, Hero J., de Vries, Johannes G., Feringa, Ben L.

Access to enantiopure compounds on large scale in an environmentally friendly and cost-efficient manner remains one of the greatest challenges in chemistry. Resolution of racemates using enantioselective liquid-liquid extraction has great potential to meet that challenge. However, a relatively feeble understanding of the chemical principles and physical properties behind this technique has hampered the development of hosts possessing sufficient resolving power for their application to large scale processes. Herein we present, employing the previously untested SPINOL based phosphoric acids host family, an in depths study of the parameters affecting the efficiency of the resolution of amino-alcohols in the optic of further understanding the core principles behind ELLE. We have systematically investigated the dependencies of the enantioselection by parameters such as the choice of solvent, the temperature, as well as the pH and bring to light many previously unsuspected and highly intriguing interactions. Furthermore, utilizing these new insights to our advantage, we developed novel, highly efficient, extraction and resolving protocols which provide remarkable levels of enantioselectivity. It was shown that the extraction is catalytic in host by demonstrating transport in a U-tube and finally it was demonstrated how the solvent dependency could be exploited in an unprecedented triphasic resolution system.

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When humans and machines collaborate: Cross-lingual Label Editing in Wikidata

2019, Kaffee, L.-A., Endris, K.M., Simperl, E.

The quality and maintainability of a knowledge graph are determined by the process in which it is created. There are different approaches to such processes; extraction or conversion of available data in the web (automated extraction of knowledge such as DBpedia from Wikipedia), community-created knowledge graphs, often by a group of experts, and hybrid approaches where humans maintain the knowledge graph alongside bots. We focus in this work on the hybrid approach of human edited knowledge graphs supported by automated tools. In particular, we analyse the editing of natural language data, i.e. labels. Labels are the entry point for humans to understand the information, and therefore need to be carefully maintained. We take a step toward the understanding of collaborative editing of humans and automated tools across languages in a knowledge graph. We use Wikidata as it has a large and active community of humans and bots working together covering over 300 languages. In this work, we analyse the different editor groups and how they interact with the different language data to understand the provenance of the current label data.

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Spider chitin: An Ultrafast Microwave-Assisted Method for Chitin Isolation from Caribena versicolor Spider Molt Cuticle

2019, Machałowski, Tomasz, Wysokowski, Marcin, Tsurkan, Mikhail V., Galli, Roberta, Schimpf, Christian, Rafaja, David, Brendler, Erica, Viehweger, Christine, Zółtowska-Aksamitowska, Sonia, Petrenko, Iaroslav, Czaczyk, Katarzyna, Kraft, Michael, Bertau, Martin, Bechmann, Nicole, Guan, Kaomei, Bornstein, Stefan R., Voronkina, Alona, Fursov, Andriy, Bejger, Magdalena, Biniek-Antosiak, Katarzyna, Rypniewski, Wojciech, Figlerowicz, Marek, Pokrovsky, Oleg, Jesionowski, Teofil, Ehrlich, Hermann

Chitin, as a fundamental polysaccharide in invertebrate skeletons, continues to be actively investigated, especially with respect to new sources and the development of effective methods for its extraction. Recent attention has been focused on marine crustaceans and sponges; however, the potential of spiders (order Araneae) as an alternative source of tubular chitin has been overlooked. In this work, we focused our attention on chitin from up to 12 cm-large Theraphosidae spiders, popularly known as tarantulas or bird-eating spiders. These organisms “lose” large quantities of cuticles during their molting cycle. Here, we present for the first time a highly effective method for the isolation of chitin from Caribena versicolor spider molt cuticle, as well as its identification and characterization using modern analytical methods. We suggest that the tube-like molt cuticle of this spider can serve as a naturally prefabricated and renewable source of tubular chitin with high potential for application in technology and biomedicine. © 2019 by the authors.

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Assessment of Phycocyanin Extraction from Cyanidium caldarium by Spark Discharges, Compared to Freeze-Thaw Cycles, Sonication, and Pulsed Electric Fields

2021, Sommer, Marie-Christine, Balazinski, Martina, Rataj, Raphael, Wenske, Sebastian, Kolb, Juergen F., Zocher, Katja

Phycocyanin is a blue colored pigment, synthesized by several species of cyanobacteria and red algae. Besides the application as a food-colorant, the pigmented protein is of high interest as a pharmaceutically and nutritionally valuable compound. Since cyanobacteria-derived phycocyanin is thermolabile, red algae that are adapted to high temperatures are an interesting source for phycocyanin extraction. Still, the extraction of high quality phycocyanin from red algae is challenging due to the strong and rigid cell wall. Since standard techniques show low yields, alternative methods are needed. Recently, spark discharges have been shown to gently disintegrate microalgae and thereby enable the efficient extraction of susceptible proteins. In this study, the applicability of spark discharges for phycocyanin extraction from the red alga Cyanidium caldarium was investigated. The efficiency of 30 min spark discharges was compared with standard treatment protocols, such as three times repeated freeze-thaw cycles, sonication, and pulsed electric fields. Input energy for all physical methods were kept constant at 11,880 J to ensure comparability. The obtained extracts were evaluated by photometric and fluorescent spectroscopy. Highest extraction yields were achieved with sonication (53 mg/g dry weight (dw)) and disintegration by spark discharges (4 mg/g dw) while neither freeze-thawing nor pulsed electric field disintegration proved effective. The protein analysis via LC-MS of the former two extracts revealed a comparable composition of phycobiliproteins. Despite the lower total concentration of phycocyanin after application of spark discharges, the purity in the raw extract was higher in comparison to the extract attained by sonication.