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Search for "α-cyclodextrin" in Full Text gives 28 result(s) in Beilstein Journal of Organic Chemistry.

Spatial arrangements of cyclodextrin host–guest complexes in solution studied by 13C NMR and molecular modelling

  • Konstantin Lebedinskiy,
  • Ivan Barvík,
  • Zdeněk Tošner,
  • Ivana Císařová,
  • Jindřich Jindřich and
  • Radim Hrdina

Beilstein J. Org. Chem. 2024, 20, 331–335, doi:10.3762/bjoc.20.33

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  • the protons 6 of molecule 1 reveals deep penetration of the guest into the cavity of α-cyclodextrin (Figure 2). All protons of 1 show ROESY cross-peaks with proton 3 of the glucose unit (see page S73 in Supporting Information File 1). For complexes of ligands with α-CD, we always performed a series of
  • ). Having established the method, we chose various cyclic compounds (noradamantane, adamantane, cyclohexane derivatives) with desired symmetry and measured NMR spectra of these guest molecules (2–8) in α-cyclodextrin and cyclodextrins with a larger cavity (β-CD and γ-CD, Figure 4). In all cases, the 1H NMR
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Published 20 Feb 2024

CO2 complexation with cyclodextrins

  • Cecilie Høgfeldt Jessen,
  • Jesper Bendix,
  • Theis Brock Nannestad,
  • Heloisa Bordallo,
  • Martin Jæger Pedersen,
  • Christian Marcus Pedersen and
  • Mikael Bols

Beilstein J. Org. Chem. 2023, 19, 1021–1027, doi:10.3762/bjoc.19.78

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  • , are studied as potential CO2 capture agents due to their unique molecular structures and high selectivity towards CO2. In this paper we have investigated binding efficiency of a number of cyclodextrins towards CO2. It is found that the crystal structure of α-cyclodextrin with CO2 has a 1:1
  • stoichioimetry and that a number of simple and modified cyclodextrins bind CO2 in water with a Kg of 0.18–1.2 bar−1 (7–35 M−1) with per-O-methyl α-cyclodextrin having the highest CO2 affinity. Keywords: carbon dioxide; crystals; cyclodextrin; gas binding; Introduction The concentration of carbon dioxide (CO2
  • CO2 is captured by non-covalent binding. Henglein and Cramer showed many years ago that α-cyclodextrin (1, Figure 1), when treated with CO2 under pressure for several days gave crystals with the gas trapped inside [8]. According to Cramer only 1 was able to form crystals, while larger cyclodextrins
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Published 17 Jul 2023

A study of the DIBAL-promoted selective debenzylation of α-cyclodextrin protected with two different benzyl groups

  • Naser-Abdul Yousefi,
  • Morten L. Zimmermann and
  • Mikael Bols

Beilstein J. Org. Chem. 2022, 18, 1553–1559, doi:10.3762/bjoc.18.165

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  • Naser-Abdul Yousefi Morten L. Zimmermann Mikael Bols Department of chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen, Denmark 10.3762/bjoc.18.165 Abstract An α-cyclodextrin protected with 2,4-dichlorobenzyl groups on the primary alcohols and ordinary benzyl groups on the
  • ; cyclodextrin; debenzylation; 2,4-dichlorobenzyl; selective; Introduction α-Cyclodextrin (1) is a cyclic carbohydrate consisting of six α-1,4-linked ᴅ-glucose molecules (Figure 1). It has a donut-like structure with the glucose residues all aligned with the α-side towards the center of the ring and the polar
  • electron-poor benzyl groups reacting much more sluggishly. Indeed the per-2,4-dichlorobenzyl (DCB) protected compound 1 was completely resistant to DIBAL even when treated for several days [15]. This led us to wonder if an α-cyclodextrin protected on the primary hydroxy groups with DCB groups and on the
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Published 17 Nov 2022

Constrained thermoresponsive polymers – new insights into fundamentals and applications

  • Patricia Flemming,
  • Alexander S. Münch,
  • Andreas Fery and
  • Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

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  • irradiation as well as by host molecule (α-cyclodextrin) complexation [278]. Due to the high number of proton acceptor/donor sites, ureido-modified copolymers such as poly(allylamine-co-allylurea) are also becoming more and more important. The critical phase transition temperature can often be finely tuned
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Published 20 Aug 2021

Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers

  • Alberto Rubin Pedrazzo,
  • Fabrizio Caldera,
  • Marco Zanetti,
  • Silvia Lucia Appleton,
  • Nilesh Kumar Dhakar and
  • Francesco Trotta

Beilstein J. Org. Chem. 2020, 16, 1554–1563, doi:10.3762/bjoc.16.127

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  • extraction) functionalized material, with a less negative ζ potential. Experimental Materials β-Cyclodextrin (β-CD), α-cyclodextrin (α-CD), and γ-cyclodextrin (γ-CD) were kindly provided by Roquette Italia SpA and Wacker Chemie. Carbonyldiimidazole (CDI, ≥97.0% (T)), 1,4-diazabicyclo[2.2.2]octane (DABCO
  • was as follows: 3.00 g of α-cyclodextrin, 3.33 g of β-cyclodextrins and 4.05 g of γ-cyclodextrins (3.30 mmol) were dissolved in 10 mL of DMF (in three different round-bottomed flasks). After complete dissolution of the cyclodextrins, 2.00 g (13 mmol) of CDI as cross linker were added to each batch
  • carbonyldiimidazole. For example, for the 1:4 ratio synthesis, 3.38 g of α-cyclodextrin, 3.75 g of β-cyclodextrins and 4.56 g of γ-cyclodextrins were placed inside a 50 mL jar containing 10 zirconia balls. The amount of CDI added in each batch to maintain the 1:4 molar ratio was 2.25 g. After 3 h of sun wheel
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Published 29 Jun 2020

Water inside β-cyclodextrin cavity: amount, stability and mechanism of binding

  • Stiliyana Pereva,
  • Valya Nikolova,
  • Silvia Angelova,
  • Tony Spassov and
  • Todor Dudev

Beilstein J. Org. Chem. 2019, 15, 1592–1600, doi:10.3762/bjoc.15.163

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  • thermodynamic characteristics of β-CD hydration compare with those of its smaller α-cyclodextrin (α-CD) counterpart? In this study, we address these questions by employing a combination of experimental (DSC/TG) and theoretical (DFT) approaches. Keywords: β-cyclodextrin; DFT calculations; DSC/TG experiments
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Published 17 Jul 2019

Enhanced single-isomer separation and pseudoenantiomer resolution of new primary rim heterobifunctionalized α-cyclodextrin derivatives

  • Iveta Tichá,
  • Gábor Benkovics,
  • Milo Malanga and
  • Jindřich Jindřich

Beilstein J. Org. Chem. 2018, 14, 2829–2837, doi:10.3762/bjoc.14.261

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Published 13 Nov 2018

Tetrathiafulvalene – a redox-switchable building block to control motion in mechanically interlocked molecules

  • Hendrik V. Schröder and
  • Christoph A. Schalley

Beilstein J. Org. Chem. 2018, 14, 2163–2185, doi:10.3762/bjoc.14.190

Graphical Abstract
  • , extended π-surfaces [64] of TTF derivatives can have a stabilizing effect upon complexation. TTF (1) also forms inclusion complexes with neutral host molecules such as cyclodextrins (Figure 6). This complexation is mainly driven by the hydrophobic effect. α-Cyclodextrin (6) molecules encapsulate the
  • of these bistable donor–acceptor rotaxanes were subsequently underpinned by several quantum mechanical studies [77][78][79]. The concept of TTF-based switchable rotaxanes was also extended to rotaxanes with other macrocycles. In Figure 13, the bistable [2]rotaxane 15 is shown with an α-cyclodextrin
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Published 20 Aug 2018

Intramolecular glycosylation

  • Xiao G. Jia and
  • Alexei V. Demchenko

Beilstein J. Org. Chem. 2017, 13, 2028–2048, doi:10.3762/bjoc.13.201

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  • synthesis of cyclodextrins is very challenging: controlling α-gluco stereoselectivity, and especially the final cyclization, represent a great challenge. For example, in Ogawa’s synthesis of α-cyclodextrin the chain assembly was non-stereoselective and the cyclization was achieved in only 21% yield [75
  • ]. Kusumoto et al. clearly demonstrated the advantage of the molecular clamping in application to the synthesis of α-cyclodextrin (Scheme 6) [51]. The tethering was used to improve the selectivity during the stepwise chain elongation via the coupling of maltose building blocks 21 and 22, as well as the
  • glycosidation. Molecular clamping with the phthaloyl linker in the synthesis of α-cyclodextrin. m-Xylylene as a rigid tether for intramolecular glycosylation. Oligosaccharide synthesis using rigid xylylene linkers. Stereo- and regiochemical outcome of peptide-based linkers. Positioning effect of donor and
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Published 29 Sep 2017

NMR reaction monitoring in flow synthesis

  • M. Victoria Gomez and
  • Antonio de la Hoz

Beilstein J. Org. Chem. 2017, 13, 285–300, doi:10.3762/bjoc.13.31

Graphical Abstract
  • dispersion of this nucleus. The authors determined the association constant of the complex of NaPF6 with α-cyclodextrin at the picomole level with a detection volume of 50 nL and using non-deuterated solvents [25]. To conclude with the different coil geometries, microslot NMR microprobes and stripline coils
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Published 14 Feb 2017

Versatile synthesis of end-reactive polyrotaxanes applicable to fabrication of supramolecular biomaterials

  • Atsushi Tamura,
  • Asato Tonegawa,
  • Yoshinori Arisaka and
  • Nobuhiko Yui

Beilstein J. Org. Chem. 2016, 12, 2883–2892, doi:10.3762/bjoc.12.287

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  • obtained from NOF Corporation (Tokyo, Japan). α-Cyclodextrin (α-CD) was obtained from Ensuiko Sugar Refining (Tokyo, Japan). 4-(Azidomethyl)benzoic acid was synthesized according to the previous report [27]. 4-Azidobenzoic acid, 4-methylbenzoic acid, p-(tert-butyl)phenylacetylene, and 2-(2-hydroxyethoxy
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Published 28 Dec 2016

Radical polymerization by a supramolecular catalyst: cyclodextrin with a RAFT reagent

  • Kohei Koyanagi,
  • Yoshinori Takashima,
  • Takashi Nakamura,
  • Hiroyasu Yamaguchi and
  • Akira Harada

Beilstein J. Org. Chem. 2016, 12, 2495–2502, doi:10.3762/bjoc.12.244

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  • transfer agent (CTA) that has α-cyclodextrin (α-CD) as a host molecule (α-CD-CTA). Prior to the polymerization of N,N-dimethylacrylamide (DMA), we investigated the complex formation of α-CD with DMA. Single X-ray analysis demonstrated that α-CD includes DMA inside its cavity. When DMA was polymerized in
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Published 22 Nov 2016

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

  • Vito Rizzi,
  • Sergio Matera,
  • Paola Semeraro,
  • Paola Fini and
  • Pinalysa Cosma

Beilstein J. Org. Chem. 2016, 12, 549–563, doi:10.3762/bjoc.12.54

Graphical Abstract
  • complexation mode of the inclusion complexes involving 4-thiothymidine (S4TdR, a known photosensitizer) and five CDs, namely 2-hydroxypropyl-α-cyclodextrin (2-HP-α-CD), 2-hydroxypropyl-β-cyclodextrin (2-HP-β-CD), 2-hydroxypropyl-γ-cyclodextrin (2-HP-γ-CD), heptakis-(2,6-di-O-methyl)-β-cyclodextrin (DIMEB CD
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Published 21 Mar 2016

Supramolecular structures based on regioisomers of cinnamyl-α-cyclodextrins – new media for capillary separation techniques

  • Gabor Benkovics,
  • Ondrej Hodek,
  • Martina Havlikova,
  • Zuzana Bosakova,
  • Pavel Coufal,
  • Milo Malanga,
  • Eva Fenyvesi,
  • Andras Darcsi,
  • Szabolcs Beni and
  • Jindrich Jindrich

Beilstein J. Org. Chem. 2016, 12, 97–109, doi:10.3762/bjoc.12.11

Graphical Abstract
  • reached higher values due to lower viscosity of the BGE. Subsequently differences between electrophoretic mobilities with and without Cin-α-CDs in BGE decreased because of smaller size of Cin-α-CDs aggregates. The studied α-cyclodextrin derivatives offer a potential for employing them in capillary
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Published 19 Jan 2016

Synthesis, structure, and mechanical properties of silica nanocomposite polyrotaxane gels

  • Kazuaki Kato,
  • Daisuke Matsui,
  • Koichi Mayumi and
  • Kohzo Ito

Beilstein J. Org. Chem. 2015, 11, 2194–2201, doi:10.3762/bjoc.11.238

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  • progress. Experimental Materials Crude polyrotaxane consisting of polyethylene glycol (PEG, Mn = 32,000) and α-cyclodextrin (CD) were purchased from Advanced Softmaterials, Inc. The crude polyrotaxane was purified by repeated reprecipitation from its DMSO solution into deionized water. The obtained
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Published 16 Nov 2015

Qualitative evaluation of regioselectivity in the formation of di- and tri-6-O-tritylates of α-cyclodextrin

  • Keisuke Yoshikiyo,
  • Yoshihisa Matsui and
  • Tatsuyuki Yamamoto

Beilstein J. Org. Chem. 2015, 11, 1530–1540, doi:10.3762/bjoc.11.168

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  • Keisuke Yoshikiyo Yoshihisa Matsui Tatsuyuki Yamamoto Faculty of Life and Environmental Science, Shimane University, 1060 Nishikawatsu, Matsue, Shimane, 690-8504, Japan 10.3762/bjoc.11.168 Abstract The quantitative analysis of reaction products showed that the reaction of 6A,6D-di-O-trityl-α
  • -cyclodextrin (CD), AD-isomer, with trityl chloride in pyridine at 55 °C gave 6A,6B,6E-tri-O-trityl-α-CD, the amount of which was only 25% of that of simultaneously formed 6A,6B,6D-tri-O-trityl-α-CD. This indicates that the bulky trityl groups of glucopyranose-A and -D (Glu-A and -D, respectively) in the AD
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Published 02 Sep 2015

Effects of RAMEA-complexed polyunsaturated fatty acids on the response of human dendritic cells to inflammatory signals

  • Éva Rajnavölgyi,
  • Renáta Laczik,
  • Viktor Kun,
  • Lajos Szente and
  • Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 3152–3160, doi:10.3762/bjoc.10.332

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  • study we monitored the effects of α-linoleic acid, eicosapentaenoic acid and docosahexaenoic acid solubilized in a dimethyl sulfoxide (DMSO)/ethanol 1:1 mixture or as complexed by randomly methylated α-cyclodextrin (RAMEA) on the inflammatory response of human monocyte-derived dendritic cells (moDC
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Published 30 Dec 2014

Release of β-galactosidase from poloxamine/α-cyclodextrin hydrogels

  • César A. Estévez,
  • José Ramón Isasi,
  • Eneko Larrañeta and
  • Itziar Vélaz

Beilstein J. Org. Chem. 2014, 10, 3127–3135, doi:10.3762/bjoc.10.330

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  • available source of calcium and protein. In this work, gels obtained by complexation of Tetronic 90R4 with α-cyclodextrin loaded with β-galactosidase are proposed as a way to administer the enzyme immediately before or with the lactose-containing meal. Both molecules are biocompatible, can form gels in situ
  • , and show sustained erosion kinetics in aqueous media. The complex was characterized by FTIR that evidenced an inclusion complex between the polyethylene oxide block and α-cyclodextrin. The release profiles of β-galactosidase from two different matrices (gels and tablets) of the in situ hydrogels have
  • , which can be used as supramolecular drug delivery systems [11]. Thus, cyclodextrin-based physical hydrogels assembled through microcrystalline formation are based upon the aggregation of polypseudorotaxane structures [12]. In the case of reverse Tetronics, α-cyclodextrin (composed of six glucose units
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Published 24 Dec 2014

A study on the inhibitory mechanism for cholesterol absorption by α-cyclodextrin administration

  • Takahiro Furune,
  • Naoko Ikuta,
  • Yoshiyuki Ishida,
  • Hinako Okamoto,
  • Daisuke Nakata,
  • Keiji Terao and
  • Norihiro Sakamoto

Beilstein J. Org. Chem. 2014, 10, 2827–2835, doi:10.3762/bjoc.10.300

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  • , α-cyclodextrin (α-CD) is reportedly one of the most powerful dietary fibers for decreasing blood cholesterol. However, it is difficult to believe that α-CD directly removes cholesterol because it has a very low affinity for cholesterol and its mechanism of action is less well understood than those
  • dietary fibers. The decrease in micellar cholesterol solubility in the FeSSIF was the strongest with α-CD addition. Keywords: α-cyclodextrin; bile salt micelles; cholesterol; lecithin; micellar solubility; Introduction α-Cyclodextrin (α-CD) is a ring molecule composed of six glucose units that has an
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Published 02 Dec 2014

Synthesis of a resin monomer-soluble polyrotaxane crosslinker containing cleavable end groups

  • Ji-Hun Seo,
  • Shino Nakagawa,
  • Koichiro Hirata and
  • Nobuhiko Yui

Beilstein J. Org. Chem. 2014, 10, 2623–2629, doi:10.3762/bjoc.10.274

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  • -soluble PRX crosslinker can be applied to design degradable photosetting plastics potentially used in the industrial or biomedical field. Keywords: α-cyclodextrin; composite resin; disulfide; polyrotaxane; Vickers hardness; Introduction Polyrotaxane (PRX) is a supermolecule containing host molecules
  • , e.g., α-cyclodextrin (α-CD), threaded on a linear guest molecule, e.g., poly(ethylene glycol) (PEG) [1]. The threaded α-CD molecules are known to be reversibly disassembled when a cleavable end-capping group was introduced in the PEGs, and the cleavable reaction was triggered by proper signals [2][3
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Published 10 Nov 2014

Synthesis of graft polyrotaxane by simultaneous capping of backbone and grafting from rings of pseudo-polyrotaxane

  • Kazuaki Kato,
  • Katsunari Inoue,
  • Masabumi Kudo and
  • Kohzo Ito

Beilstein J. Org. Chem. 2014, 10, 2573–2579, doi:10.3762/bjoc.10.269

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  • (PEG) and the formation of inclusion complexes with α-cyclodextrin (α-CD). PEG with multiple functional groups at each end was prepared by the condensation of PEG-amine and D-gluconic acid; the PEG derivative formed an inclusion complex with α-CD. The polymerization of multiple hydroxy groups at the
  • chromatography (SEC) with a calibration curve using PEG standards. The standard polymers for the calibration of the molecular weights by SEC were purchased from Polymer Source Inc. α-Cyclodextrin (α-CD) was purchased from Nihon Shokuhin Kako Co. Ltd. 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) was purchased from
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Published 04 Nov 2014

Effect of cyclodextrin complexation on phenylpropanoids’ solubility and antioxidant activity

  • Miriana Kfoury,
  • David Landy,
  • Lizette Auezova,
  • Hélène Greige-Gerges and
  • Sophie Fourmentin

Beilstein J. Org. Chem. 2014, 10, 2322–2331, doi:10.3762/bjoc.10.241

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  • , stability, release and bioavailability of natural compounds [10][11][12][13]. CDs are a family of cyclic oligosaccharides obtained from enzymatic degradation of starch. The most common native CDs are α-cyclodextrin (α-CD), β-cyclodextrin (β-CD) and γ-cyclodextrin (γ-CD) composed of six, seven and eight (α
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Published 06 Oct 2014

A complete series of 6-deoxy-monosubstituted tetraalkylammonium derivatives of α-, β-, and γ-cyclodextrin with 1, 2, and 3 permanent positive charges

  • Martin Popr,
  • Simona Hybelbauerová and
  • Jindřich Jindřich

Beilstein J. Org. Chem. 2014, 10, 1390–1396, doi:10.3762/bjoc.10.142

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  • mixture of products with several degrees of substitution. The recently published purification procedure [16] yielded just this mixture. The purification on a column of activated charcoal was also described [28]. We found the most convenient purification method to obtain 6I-O-p-toluenesulfonyl-α
  • -cyclodextrin (2) and 6I-O-p-toluenesulfonyl-γ-cyclodextrin (3) is flash column chromatography on a reverse phase C18 column with a step gradient. The use of this method allowed for the recovery of about 40% of the starting α- or γ-CD by flushing the column with 10% MeOH. Pure monotosylated product is then
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Published 18 Jun 2014

Substitution effect and effect of axle’s flexibility at (pseudo-)rotaxanes

  • Friedrich Malberg,
  • Jan Gerit Brandenburg,
  • Werner Reckien,
  • Oldamur Hollóczki,
  • Stefan Grimme and
  • Barbara Kirchner

Beilstein J. Org. Chem. 2014, 10, 1299–1307, doi:10.3762/bjoc.10.131

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  • computational energy profile [22]. The formation of α-cyclodextrin-based [3]pseudorotaxanes in the gas phase was studied by means of density functional calculations [23]. Molecular mechanics calculations were used for a free energy calculation of an α-cyclodextrin rotaxane system and for the investigation of
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Published 05 Jun 2014

Linkage of α-cyclodextrin-terminated poly(dimethylsiloxanes) by inclusion of quasi bifunctional ferrocene

  • Helmut Ritter,
  • Berit Knudsen and
  • Valerij Durnev

Beilstein J. Org. Chem. 2013, 9, 1278–1284, doi:10.3762/bjoc.9.144

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  • -toluenesulfonyl)-6-deoxy)-α-cyclodextrin (α-tosyl-CD), mono-(6-N-allylamino)-6-deoxy)-α-cyclodextrin (AAm-α-CD) and mono-((6-N-allylamino)-6-deoxy)-peracetylated-α-cyclodextrin (AAm-Ac-α-CD) [21] were synthesized according to the literature. MALDI–TOF mass spectra were recorded with a Bruker Ultraflex time-of
  • -cyclodextrin-dimethyldisiloxane (α-CD-disiloxane) (4): Mono-((6-N-allylamino)-6-deoxy)-peracetylated-α-cyclodextrin (0.70 g, 0.40 mmol) is dissolved in 30 mL of dry toluene under an argon atmosphere at 45 °C. 1,1,3,3-Tetramethyldisiloxane (0.04 mL, 0.20 mmol) is added. In a period of 5 h, the Karstedt catalyst
  • ), 2.06–2.16 (m, 108H, CH3CO), 3.80 (m, 12H), 4.15 (m, 12H), 4.42 (m, 24H), 4.74–4.78 (m, 12H), 5.04 (m, 12H), 5.55 (m, 12H); ESI–MS m/z: 3148.34 [M + Na]+. Synthesis of mono-((6-N-allylamino)-6-deoxy)-peracetylated-α-cyclodextrin-polymethylsiloxane (α-CD-PDMS) (5): Mono-((6-N-allylamino)-6-deoxy
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Published 01 Jul 2013
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