¹⁹F NMR as a tool in chemical biology

• Diana Gimenez,
• Aoife Phelan,
• Cormac D. Murphy and
• Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

• -structural protein 1 (NS1A) homodimer (Figure 9) [64]. Protein NS1A is a highly conserved virulence factor from influenza virus (H3N2) comprised of an N-terminal double-stranded RNA (dsRNA)-binding domain (RBD) and a multifunctional C-terminal effector domain (ED), each of which can independently form

The preparation and properties of 1,1-difluorocyclopropane derivatives

• Kymbat S. Adekenova,
• Peter B. Wyatt and
• Sergazy M. Adekenov

Beilstein J. Org. Chem. 2021, 17, 245–272, doi:10.3762/bjoc.17.25

Supramolecular polymerization of sulfated dendritic peptide amphiphiles into multivalent L-selectin binders

• David Straßburger,
• Svenja Herziger,
• Katharina Huth,
• Moritz Urschbach,
• Rainer Haag and
• Pol Besenius

Beilstein J. Org. Chem. 2021, 17, 97–104, doi:10.3762/bjoc.17.10

• applicable platform to prepare and evaluate anti-inflammatory materials using multicomponent and multifunctional supramolecular subunits. Analysis of the self-assembly behavior of I by A: CD-spectra of 5, 10, 25 or 50 µM aqueous solutions; B, and C: TEM micrographs of negatively stained 25 µM solutions in

Et₃N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties

• Dharmender Singh,
• Vipin Kumar and
• Virender Singh

Beilstein J. Org. Chem. 2020, 16, 1740–1753, doi:10.3762/bjoc.16.146

• incorporation of sulfur to generate multifunctional β-carboline-linked benzothiophenones in good to excellent yields. The synthetic strategy could also be extended towards the synthesis of β-carboline-linked benzothiophenes. Moreover, the afforded products emerged as promising fluorophores and displayed

Nonenzymatic synthesis of anomerically pure, mannosyl-based molecular probes for scramblase identification studies

• Giovanni Picca,
• Markus Probst,
• Simon M. Langenegger,
• Oleg Khorev,
• Peter Bütikofer,
• Anant K. Menon and
• Robert Häner

Beilstein J. Org. Chem. 2020, 16, 1732–1739, doi:10.3762/bjoc.16.145

• glycolipid analogs; scramblase; Introduction Mannosyl phosphoryl dolichol (MPD), an important, multifunctional glycolipid, is used as a mannose donor for protein N-glycosylation, O- and C-mannosylation, and glycosylphosphatidylinositol (GPI) anchoring in the luminal leaflet of the endoplasmic reticulum (ER

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

• crosslinked polymers made up of cyclodextrins. The reactive hydroxy groups of CDs allow them to act as multifunctional monomers capable of crosslinking to bi- or multifunctional chemicals. The most common NS synthetic pathway consists in dissolving the chosen CD and an appropriate crosslinker in organic polar

• allow them to act as polyfunctional monomers, permitting the crosslinking with bi- or multifunctional chemicals, such as dianhydrides, diisocyanates, diepoxides, and dicarboxylic acids, etc. The polarity and size of the polymer network can be easily tuned by varying the type of the crosslinker and

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

• Nuray Altinolcek,
• Ahmet Battal,
• Mustafa Tavasli,
• William J. Peveler,
• Holly A. Yu and
• Peter J. Skabara

Beilstein J. Org. Chem. 2020, 16, 1066–1074, doi:10.3762/bjoc.16.93

• [21][22][23]. Research continues on carbazole derivatives to find new materials with novel properties. It is therefore essential that one should design a molecule that has multifunctional usage in many different areas of technology [24]. Since carbazole is a relatively inexpensive material with unique

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

• Rodrigo Costa e Silva,
• Luely Oliveira da Silva,
• Aloisio de Andrade Bartolomeu,
• Timothy John Brocksom and
• Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

• studies on this reaction are ongoing with initial suggestions of the coupling between the sulfonyl radical and the radical alkene as a key step for this transformation. In 2019, Ghaffari-Moghaddam, Oveisi and co-workers reported the synthesis of a new multifunctional MOF, namely Fe@PCN-222(Fe), and its

Aldehydes as powerful initiators for photochemical transformations

• Maria A. Theodoropoulou,
• Nikolaos F. Nikitas and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2020, 16, 833–857, doi:10.3762/bjoc.16.76

• two different types of free radical intermediates, 30 and 31 (Scheme 8). The species 31 was shown to be the primary initiating radical compound. In 2006, Aydin and Arsu employed benzaldehyde (8) as the coinitiator for the photoinitiated free radical polymerization of multifunctional MMA (26) [38

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

• Bernd Strehmel,
• Christian Schmitz,
• Ceren Kütahya,
• Yulian Pang,
• Anke Drewitz and
• Heinz Mustroph

Beilstein J. Org. Chem. 2020, 16, 415–444, doi:10.3762/bjoc.16.40

• surroundings is the biggest challenge in practical applications of these systems. Thus, counter ions such as n-C12H25-Ph-SO3− (8, 10, 79, 81), NTf2− (4) or [Al(OC4F9)4]− (37) depict alternatives resulting in a solubility of 10–30 g/L in reactive monomers such as multifunctional acrylates [5], printing inks or

A combinatorial approach to improving the performance of azoarene photoswitches

• Joaquin Calbo,
• Aditya R. Thawani,
• Rosina S. L. Gibson,
• Andrew J. P. White and
• Matthew J. Fuchter

Beilstein J. Org. Chem. 2019, 15, 2753–2764, doi:10.3762/bjoc.15.266

• 10.3762/bjoc.15.266 Abstract Azoarenes remain privileged photoswitches – molecules that can be interconverted between two states using light – enabling a huge range of light addressable multifunctional systems and materials. Two key innovations to improve the addressability and Z-isomer stability of the

• Photoswitches are molecules that are capable of being reversibly interconverted between (at least) two states by means of light irradiation. The incorporation of photoswitches into multifunctional systems has huge relevance to next-generation materials, with a plethora of applications that range from

Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization

• Valentina A. Ol’shevskaya,
• Elena G. Kononova and
• Andrei V. Zaitsev

Beilstein J. Org. Chem. 2019, 15, 2704–2709, doi:10.3762/bjoc.15.263

• widely used to generate singlet oxygen for PDT applications [9][23]. We intend here to combine within one molecule the structural specificity of a meso-fuorinated porphyrin/chlorin macrocycle and maleimide units to develop novel multifunctional compounds with improved properties for various applications

Targeted photoswitchable imaging of intracellular glutathione by a photochromic glycosheet sensor

• Xianzhi Chai,
• Hai-Hao Han,
• Yi Zang,
• Jia Li,
• Xiao-Peng He,
• Junji Zhang and
• He Tian

Beilstein J. Org. Chem. 2019, 15, 2380–2389, doi:10.3762/bjoc.15.230

• enables the specific cell-targetability of Glyco-DTE@MnO2 hybrid sensor. Compared to conventional GSH biosensors, our strategy offers a simple yet smart design that circumvents the elaborate molecular design and laborious synthesis for multifunctional sensors, further broadening the availability of

Metal-free mechanochemical oxidations in Ertalyte^® jars

• Andrea Porcheddu,
• Francesco Delogu,
• Lidia De Luca,
• Claudia Fattuoni and
• Evelina Colacino

Beilstein J. Org. Chem. 2019, 15, 1786–1794, doi:10.3762/bjoc.15.172

• : multifunctional polymer composites based on grown materials). A. P. is grateful to MIUR for “Finanziamento delle Attività Base di Ricerca (FABR 2017)“.

A heteroditopic macrocycle as organocatalytic nanoreactor for pyrroloacridinone synthesis in water

• Piyali Sarkar,
• Sayan Sarkar and
• Pradyut Ghosh

Beilstein J. Org. Chem. 2019, 15, 1505–1514, doi:10.3762/bjoc.15.152

• aggregation tendency. Herein we have extensively explored a multifunctional macrocycle (BATA-MC), comprising bis-amide and tris-amine functionalities as H-bond donor/acceptor moieties, and parallel benzene moieties for aromatic π–π stacking interactions as an organocatalytic nanoreactor for organic

• transformations, in particular, for the synthesis of biologically important highly substituted pyrroloacridines in the ecofriendly solvent water. Results and Discussion Synthesis of the macrocycle Considerable efforts in synthesizing multifunctional macrocycles have been dedicated lately for the construction of

• ][47][48][49][50]. The multifunctional macrocycle BATA-MC (Figure 1) has been successfully applied as a wheel in the molecular rotors fields [51]. Considering its multiple binding sites (π-interactions, H-bonding site, cavity), we investigated the catalytic activity of this macrocycle. BATA-MC was

Fabrication, characterization and adsorption properties of cucurbit[7]uril-functionalized polycaprolactone electrospun nanofibrous membranes

• Changzhong Chen,
• Fengbo Liu,
• Xiongzhi Zhang,
• Zhiyong Zhao and
• Simin Liu

Beilstein J. Org. Chem. 2019, 15, 992–999, doi:10.3762/bjoc.15.97

• isotherm model. Keywords: adsorption; cucurbit[7]uril; electrospinning; macrocycles; methylene blue; nanofiber; Introduction Electrospinning is recognized as the most simple and versatile method to fabricate multifunctional nanofibers from the solution or melt of polymers, polymer/nanoparticle mixtures

Homo- and hetero-difunctionalized β-cyclodextrins: Short direct synthesis in gram scale and analysis of regiochemistry

• Gábor Benkovics,
• Mihály Bálint,
• Éva Fenyvesi,
• Erzsébet Varga,
• Szabolcs Béni,
• Konstantina Yannakopoulou and
• Milo Malanga

Beilstein J. Org. Chem. 2019, 15, 710–720, doi:10.3762/bjoc.15.66

• based on stereoselective interactions of CDs with guest molecules (chiral separations, asymmetric catalysis, enzyme mimics) [20]. However, if the target is only the side-selectivity of difunctionalization, pseudoenantiomeric mixtures of the regioisomers can be used [21]. For CD-based multifunctional

The LANCA three-component reaction to highly substituted β-ketoenamides – versatile intermediates for the synthesis of functionalized pyridine, pyrimidine, oxazole and quinoxaline derivatives

• Tilman Lechel,
• Roopender Kumar,
• Mrinal K. Bera,
• Reinhold Zimmer and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2019, 15, 655–678, doi:10.3762/bjoc.15.61

• be due to their low solubility in ethereal solvents at low temperatures – a problem that could only partially be solved by use of DMF as cosolvent. The yields of β-ketoenamides KE44–46 are only in the range of 25%, but the three-component approach to unique multifunctional products is nevertheless

A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety

• Ilya V. Taydakov,
• Yuliya M. Kreshchenova and
• Ekaterina P. Dolotova

Beilstein J. Org. Chem. 2018, 14, 3106–3111, doi:10.3762/bjoc.14.290

• MS measurements was provided by the Russian Foundation for Basic Research (grants No. 18-29-04029 and 18-02-00653). IVT is also grateful to Volkswagenstiftung (Project «Multifunctional molecular materials – bridging magnetism and luminescence»). The authors are thankful to Dr. Yu. Belousov (LPI) for

Organometallic vs organic photoredox catalysts for photocuring reactions in the visible region

• Aude-Héloise Bonardi,
• Frédéric Dumur,
• Guillaume Noirbent,
• Jacques Lalevée and
• Didier Gigmes

Beilstein J. Org. Chem. 2018, 14, 3025–3046, doi:10.3762/bjoc.14.282

• regenerates the catalyst. As it is a fast-growing field, this review will be mainly focused on an overview of the recent advances concerning the development of organic and organometallic photoredox catalysts for the photoreticulation of multifunctional monomers for a rapid and efficient access to 3D polymer

• photoreticulation processes of multifunctional radical (acrylate, methacrylate…) or cationic (epoxide) monomers. Undoubtedly, the advantage of the photoredox catalysis approach is the high efficiency of the system to initiate the polymerization upon mild light irradiation conditions (as the catalyst is regenerated

Comparative cell biological study of in vitro antitumor and antimetastatic activity on melanoma cells of GnRH-III-containing conjugates modified with short-chain fatty acids

• Eszter Lajkó,
• Sarah Spring,
• Rózsa Hegedüs,
• Beáta Biri-Kovács,
• Sven Ingebrandt,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 2495–2509, doi:10.3762/bjoc.14.226

• , adhesion inducer and cell movement inhibitory effect, [4Lys(Bu)]-GnRH-III(Dau=Aoa) proved to be the best candidate in our study for application in the targeted melanoma therapy as a multifunctional antitumor and antimetastatic drug delivery system. Schematic structure of Dau-conjugated GnRH-III or its

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

• Michael K. Bogdos,
• Emmanuel Pinard and
• John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

• )disulfide (empirical name – dichlorodiphenyl disulfide, abbreviated as DDDS), 2,6-lutidine and acridinium salts under blue LED irradiation, providing access to precious, non-commercially available and multifunctional amine building blocks in one step (Scheme 2) [40]. The group demonstrated the synthesis of

A self-assembled photoresponsive gel consisting of chiral nanofibers

• Lei Zou,
• Dan Han,
• Zhiyi Yuan,
• Dongdong Chang and
• Xiang Ma

Beilstein J. Org. Chem. 2018, 14, 1994–2001, doi:10.3762/bjoc.14.174

• and co-workers [20][21][22][23][24][25][26][27][28][29][30][31] have built a multifunctional controllable gel system, which utilized L-glutamic lipid to construct nanofibers, nanotwists, and nanotubes with the property of chirality. Azobenzene, which is structurally photosensitive, is widely chosen to

Anomeric modification of carbohydrates using the Mitsunobu reaction

• Julia Hain,
• Patrick Rollin,
• Werner Klaffke and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1619–1636, doi:10.3762/bjoc.14.138

• cannot be regarded as a classical secondary alcohol group but as a hemiacetal OH, it can be successfully involved in Mitsunobu reactions to achieve 1-O-acyl glycoses. Thus, searching for an efficient protocol for the preparation of complex, multifunctional glycosyl esters in the context of the total

• photoswitchable azobenzene α-D-mannoside 47 (Scheme 9) [46]. Notably, in this reaction, traces of an anomeric mixture of the respective furanoside 48 were detected. The Mitsunobu synthesis of aryl glycosides was also applied to p-nitrophenol [47], naphthols [48][49], or multifunctional phenols [27][50]. Such

Drug targeting to decrease cardiotoxicity – determination of the cytotoxic effect of GnRH-based conjugates containing doxorubicin, daunorubicin and methotrexate on human cardiomyocytes and endothelial cells

• Livia Polgár,
• Eszter Lajkó,
• Pál Soós,
• Orsolya Láng,
• Marilena Manea,
• Béla Merkely,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 1583–1594, doi:10.3762/bjoc.14.136

• . Seven conjugates with no cytotoxic effect on either cell types were identified, with two more conjugates with significantly milder cytotoxic effect. Based on these results, the monomeric GnRH-III(Dau=Aoa), the two multifunctional conjugates, [4Lys(Dau=Aoa)]-GnRH-III(Dau=Aoa) and GnRH-III(Dau=Aoa-K(Dau

• =Aoa)), the modified GnRH-III containing compound, ([4N-MeSer]-GnRH-III(Dau), the dimeric {GnRH-III(Dau-C)}2 and the two multifunctional conjugates containing two different chemotherapeutic drugs, GnRH-III(Mtx-K(Dau=Aoa)) and [4Lys(Mtx)]-GnRH-III(Dau=Aoa) are considered ideal compounds for tumor