Deciphering the mechanism of γ-cyclodextrin’s hydrophobic cavity hydration: an integrated experimental and theoretical study

• Stiliyana Pereva,
• Stefan Dobrev,
• Tsveta Sarafska,
• Valya Nikolova,
• Silvia Angelova,
• Tony Spassov and
• Todor Dudev

Beilstein J. Org. Chem. 2024, 20, 2635–2643, doi:10.3762/bjoc.20.221

• most stable (a/b structures from Figure 2) γ-CD–nH2O (n = 1–7) complexes with water molecules trapped in the CD cavity and not protruding out. DSC curve (A) and TG analysis for γ-CD (B). Compared to our previous studies, the hydrated γ-cyclodextrin (with 7 H2O molecules) is placed in the middle between

Synthesis and characterization of water-soluble C₆₀–peptide conjugates

• Yue Ma,
• Lorenzo Persi and
• Yoko Yamakoshi

Beilstein J. Org. Chem. 2024, 20, 777–786, doi:10.3762/bjoc.20.71

• solubility [14][15]. As early examples of the latter approach in the 1990s, Wennerström and co-workers reported the study of supramolecular BiCAP complexation of C60 with γ-cyclodextrin (γ-CD) [16]. Shinkai and co-workers synthesized water-soluble calixarene derivatives to form water-soluble complexes with

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

• Fatemeh Doraghi,
• Seyedeh Pegah Aledavoud,
• Mehdi Ghanbarlou,
• Bagher Larijani and
• Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

• low reactivity of these phthalimides, 10 mol % of catalyst was required. Cross-coupling reaction of sulfoximines 44 with N‑(arylthio)succinimides 1 catalyzed by a nanomaterial containing hexagonal boron nitride (h-BN) and γ-cyclodextrin-supported copper(II) acetate (h-BN@γ-CD@Cu(OAc)2) was developed

Inclusion complexes of the steroid hormones 17β-estradiol and progesterone with β- and γ-cyclodextrin hosts: syntheses, X-ray structures, thermal analyses and API solubility enhancements

• Alexios I. Vicatos,
• Zakiena Hoossen and
• Mino R. Caira

Beilstein J. Org. Chem. 2022, 18, 1749–1762, doi:10.3762/bjoc.18.184

• ,) with purity >98% and progesterone (C21H30O2) with purity >98% were purchased from Sigma-Aldrich Chemie GmbH (Steinheim, Germany). β-Cyclodextrin (β-CD; C42H70O35) with purity >98% and water content 13.7(1)% (n = 2) was purchased from Cyclolab (Budapest, Hungary), while γ-cyclodextrin (γ-CD; C48H80O40

Preparation of β-cyclodextrin-based dimers with selectively methylated rims and their use for solubilization of tetracene

• Konstantin Lebedinskiy,
• Volodymyr Lobaz and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2022, 18, 1596–1606, doi:10.3762/bjoc.18.170

• interaction's existence. The obtained results give hope for a successful continuation of the study with higher acenes. Experimental Materials. α- (14), β- (13), and γ-cyclodextrin (15) were purchased from Wacker Chemie AG; methyl tosylate was purchased from Acros Organics; the remaining chemicals were bought

• SiliCycle was used for column chromatography. The solvents were supplied by Penta and were distilled before use. The course of the reactions was followed on TLC Silica gel 60 F254 bought from Merck company. For the UV measurements, α-, β-, and γ-cyclodextrin were recrystallized from hot water or a water

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

• 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

Synthesis of a [6]rotaxane with singly threaded γ-cyclodextrins as a single stereoisomer

• Jason Yin Hei Man and
• Ho Yu Au-Yeung

Beilstein J. Org. Chem. 2019, 15, 1829–1837, doi:10.3762/bjoc.15.177

• Jason Yin Hei Man Ho Yu Au-Yeung Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. China 10.3762/bjoc.15.177 Abstract A series of hetero [4]-, [5]- and [6]rotaxanes containing both cucurbit[6]uril (CB[6]) and γ-cyclodextrin (γ-CD) as the macrocyclic components

An uracil-linked hydroxyflavone probe for the recognition of ATP

• Márton Bojtár,
• Péter Zoltán Janzsó-Berend,
• Dávid Mester,
• Dóra Hessz,
• Mihály Kállay,
• Miklós Kubinyi and
• István Bitter

Beilstein J. Org. Chem. 2018, 14, 747–755, doi:10.3762/bjoc.14.63

• stock solution in DMSO. The addition of γ-cyclodextrin as a solubilizer to the samples (HEPES buffer, pH 7.4) did not alter the spectra significantly, but provided a stable solution suitable for absorption and fluorescence titration experiments. The fluorescence spectra of UHF in the presence of ATP in

• constants in the range of 0.3–3∙103 M−1, considerably lower values. The effect of γ-cyclodextrin was examined in some preliminary experiments. Lowering the concentration to 0.05 mM resulted in unreliable spectra due to possible precipitation of the complex. A higher cyclodextrin concentration resulted in

• experiments, 0.02 M HEPES was used as buffer solution. Since the solubility of UHF in pure water is negligible, a stock solution of 1.0 mM was prepared in DMSO which was diluted with the buffered solution of γ-cyclodextrin (0.1 mM) and the analyte. The DMSO content in these samples was well below 1%. Each

Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of γ-cyclodextrin

• Markéta Bláhová,
• Sergey K. Filippov,
• Lubomír Kováčik,
• Jiří Horský,
• Simona Hybelbauerová,
• Zdenka Syrová,
• Tomáš Křížek and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2017, 13, 2509–2520, doi:10.3762/bjoc.13.248

• , Hlavova 8, 128 43, Prague 2, Czech Republic Department of Analytical Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43, Prague 2, Czech Republic 10.3762/bjoc.13.248 Abstract Monosubstituted derivatives of γ-cyclodextrin (γ-CD) are suitable building blocks for supramolecular polymers

• . Keywords: γ-cyclodextrin; naphthylallyl derivatives; regioselective alkylation; supramolecular properties; synthesis; Introduction Cyclodextrins [1] (CDs) are cyclic oligosaccharides with a cone-shaped cavity formed by α-1,4-linked D-glucopyranose units. The most widely used CDs are α-, β-, and γ-CD with

Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound

• Joana M. Pais,
• Maria João Barroca,
• Maria Paula M. Marques,
• Filipe A. Almeida Paz and
• Susana S. Braga

Beilstein J. Org. Chem. 2017, 13, 2138–2145, doi:10.3762/bjoc.13.212

• the DPPH· (EC50) can be determined (Table 2). Under our experimental conditions, the EC50 of fisetin was ca. 50 μM, which remained practically unaltered upon inclusion into γ-cyclodextrin. An attempted comparison with values reported in the literature for fisetin (Table 2) is difficult, as the EC50

Phosphated cyclodextrins as water-soluble chiral NMR solvating agents for cationic compounds

• Cira Mollings Puentes and
• Thomas J. Wenzel

Beilstein J. Org. Chem. 2017, 13, 43–53, doi:10.3762/bjoc.13.6

• . Experimental I. Reagents Sodium salts of phosphated α-, β- and γ-cyclodextrin with low (2–6) and high DS (6–10) were obtained from CarboMer Inc., San Diego, California. The P-CDs were refrigerated between 2–8 °C until use as recommended by the manufacturer. Substrates were obtained from commercial sources

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

• 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

Supramolecular polymer assembly in aqueous solution arising from cyclodextrin host–guest complexation

• Jie Wang,
• Zhiqiang Qiu,
• Yiming Wang,
• Li Li,
• Xuhong Guo,
• Duc-Truc Pham,
• Stephen F. Lincoln and
• Robert K. Prud’homme

Beilstein J. Org. Chem. 2016, 12, 50–72, doi:10.3762/bjoc.12.7

• enzymes used are cyclodextrin glucosyltransferases which are produced by several microorganisms including Bacillus macerans and Bacillus circulans. The most common cyclodextrins are α-, β- and γ-cyclodextrin (α-, β- and γ-CD) which consist of 6, 7 and 8 α-1,4-linked D-glucopyranose subunits, respectively

Synthesis and photophysical characteristics of polyfluorene polyrotaxanes

• Aurica Farcas,
• Giulia Tregnago,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert and
• Franco Cacialli

Beilstein J. Org. Chem. 2015, 11, 2677–2688, doi:10.3762/bjoc.11.288

• and 3·TM-γCD) have been synthesized by the coupling of 2,7-dibromofluorene encapsulated into 2,3,6-tri-O-methyl-β- or γ-cyclodextrin (TM-βCD, TM-γCD) cavities with 9,9-dioctylfluorene-2,7-diboronic acid bis(1,3-propanediol) ester. Their optical, electrochemical and morphological properties have been

Self-assemblies of γ-CDs with pentablock copolymers PMA-PPO-PEO-PPO-PMA and endcapping via atom transfer radical polymerization of 2-methacryloyloxyethyl phosphorylcholine

• Jing Lin,
• Tao Kong,
• Lin Ye,
• Ai-ying Zhang and
• Zeng-guo Feng

Beilstein J. Org. Chem. 2015, 11, 2267–2277, doi:10.3762/bjoc.11.247

• , USA. γ-Cyclodextrin (γ-CD) and 4-dimethylaminopyridine (DMAP) were supplied by TCI, Japan. Triethylamine (TEA) was purchased from VAS Chemical Reagents Company, China and refluxed with p-toluenesulfonyl chloride and distilled. 2-Methacryloyloxyethyl phosphorylcholine (MPC) was supplied by Joy Nature

Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs

• Lisa F. Becker,
• Dennis H. Schwarz and
• Gerhard Wenz

Beilstein J. Org. Chem. 2014, 10, 2920–2927, doi:10.3762/bjoc.10.310

• Lisa F. Becker Dennis H. Schwarz Gerhard Wenz Organic Macromolecular Chemistry, Saarland University, Campus C4.2, 66123 Saarbrücken, Germany 10.3762/bjoc.10.310 Abstract Methyl and ethyl thioether groups were introduced at all primary positions of α-, β-, and γ-cyclodextrin by nucleophilic

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

• , 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

The effect of permodified cyclodextrins encapsulation on the photophysical properties of a polyfluorene with randomly distributed electron-donor and rotaxane electron-acceptor units

• Aurica Farcas,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert,
• Flavian Farcas,
• Iuliana Stoica and
• Anton Airinei

Beilstein J. Org. Chem. 2014, 10, 2145–2156, doi:10.3762/bjoc.10.222

• polyrotaxanes (4a and 4b), which consist of electron-accepting 9,9-dicyanomethylenefluorene 1 as an inclusion complex in persilylated β- or γ-cyclodextrin (TMS-β-CD, TMS-γ-CD) (1a, 1b) and methyltriphenylamine as an electron-donating molecule. They are statistically distributed into the conjugated chains of 9,9

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

• ; regioselectivity; tetraalkylammonium derivatives; Introduction Cyclodextrins (CDs) are cyclic oligosaccharides with the shape of a hollow truncated cone, first described in 1891 by Villiers [1]. Naturally occurring CDs are named α-, β- and γ-cyclodextrin and are composed of 6, 7 or 8 D-glucopyranose units

• -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

• -exchange resin in a H+ cycle by flushing the column firstly with H2O to elute 3,6-anhydro-β-cyclodextrin and then with aqueous NH4HCO3 to elute the product. The yield of the reaction was 71%. Derivatives of α- and γ-cyclodextrin (5 and 6) with one tetralkylammonium group were prepared by the identical

Topochemical control of the photodimerization of aromatic compounds by γ-cyclodextrin thioethers in aqueous solution

• Hai Ming Wang and
• Gerhard Wenz

Beilstein J. Org. Chem. 2013, 9, 1858–1866, doi:10.3762/bjoc.9.217

• Hai Ming Wang Gerhard Wenz Organic Macromolecular Chemistry, Saarland University, Campus Saarbrücken C4 2, 66123 Saarbrücken, Germany 10.3762/bjoc.9.217 Abstract The formation of soluble 1:2 complexes within hydrophilic γ-cyclodextrin (γ-CD) thioethers allows to perform photodimerizations of

Inclusion of the insecticide fenitrothion in dimethylated-β-cyclodextrin: unusual guest disorder in the solid state and efficient retardation of the hydrolysis rate of the complexed guest in alkaline solution

• Dyanne L. Cruickshank,
• Natalia M. Rougier,
• Raquel V. Vico,
• Susan A. Bourne,
• Elba I. Buján,
• Mino R. Caira and
• Rita H. de Rossi

Beilstein J. Org. Chem. 2013, 9, 106–117, doi:10.3762/bjoc.9.14

• of DIMEB showed a remarkable reduction of 84% in the rate of this reaction relative to that for the free substrate, a value exceeding those previously attained with the native hosts, β- and γ-cyclodextrin, and fully methylated β-cyclodextrin. Keywords: crystal structure; cyclodextrin; fenitrothion

Cyclodextrin-based nanosponges as drug carriers

• Francesco Trotta,
• Marco Zanetti and
• Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235

• nanosponges have shown an ability to store large amounts of carbon dioxide, 1-methylcyclopropene and oxygen [8]. Three different cyclodextrin nanosponges were synthesised cross-linking α-, β- or γ-cyclodextrin with carbonyldiimidazole as oxygen-encapsulating formulations [50]. The nanosponges were able to

Molecular solubilization of fullerene C₆₀ in water by γ-cyclodextrin thioethers

• Hai Ming Wang and
• Gerhard Wenz

Beilstein J. Org. Chem. 2012, 8, 1644–1651, doi:10.3762/bjoc.8.188

• Hai Ming Wang Gerhard Wenz Organische Makromolekulare Chemie, Saarland University, Campus Geb. C4.2, D-66123, Saarbrücken, Germany 10.3762/bjoc.8.188 Abstract Various hydrophilic γ-cyclodextrin (CD) thioethers, containing neutral or ionic side arms were found to form molecular disperse solutions

Restructuring polymers via nanoconfinement and subsequent release

• Alan E. Tonelli

Beilstein J. Org. Chem. 2012, 8, 1318–1332, doi:10.3762/bjoc.8.151

• reorganize both morphologically and conformationally, either by formation of a crystalline inclusion complex (IC) between guest PET and host γ-cyclodextrin (γ-CD), followed by removal of the host γ-CD and coalescence of the guest PET (c-PET), or by precipitation (p-PET) from its solution in trifluoroacetic

Cyclodextrin nanosponge-sensitized enantiodifferentiating photoisomerization of cyclooctene and 1,3-cyclooctadiene

• Wenting Liang,
• Cheng Yang,
• Masaki Nishijima,
• Gaku Fukuhara,
• Tadashi Mori,
• Andrea Mele,
• Franca Castiglione,
• Fabrizio Caldera,
• Francesco Trotta and
• Yoshihisa Inoue

Beilstein J. Org. Chem. 2012, 8, 1305–1311, doi:10.3762/bjoc.8.149

• )-cyclooctene and (Z,Z)-1,3-cyclooctadiene were performed by using the pyromellitate-linked cyclodextrin network polymer, termed “cyclodextrin nanosponge (CDNS)”, as a supramolecular sensitizing host. The photochirogenic behavior of the nanosponges incorporating β- or γ-cyclodextrin was significantly different

• ). Enantiodifferentiating photoisomerizations of 1Z and 2ZZ sensitized by β- and γ-cyclodextrin nanosponges (CDNSs) cross linked by pyromellitic dianhydride (PDA). Representative enantiodifferentiating photosensitization of 1Z and 2ZZ with conventional and supramolecular photosensitizers. Enantiodifferentiating