An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

• Eirinaios I. Vrettos,
• Gábor Mező and
• Andreas G. Tzakos

Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

Local energy decomposition analysis of hydrogen-bonded dimers within a domain-based pair natural orbital coupled cluster study

• Ahmet Altun,
• Frank Neese and
• Giovanni Bistoni

Beilstein J. Org. Chem. 2018, 14, 919–929, doi:10.3762/bjoc.14.79

• (b) HF dimer. Schematic representation of strong pair excitations in the framework of the DLPNO-CCSD(T) method. Electronic preparation arises from excitations occurring within the same fragment, which are not shown. Only the charge transfer excitations from X to Y are shown. Analogous charge transfer

Crystal structure of the inclusion complex of cholesterol in β-cyclodextrin and molecular dynamics studies

• Elias Christoforides,
• Andreas Papaioannou and
• Kostas Bethanis

Beilstein J. Org. Chem. 2018, 14, 838–848, doi:10.3762/bjoc.14.69

• term is often problematic as the normal mode lacks information of the conformational entropy and alternative methods do not give converged results [51]. Thus, this term is usually omitted and the comparison between similar complexes is based on the ΔGGB solely. Schematic representation of (a) the

Nanoreactors for green catalysis

• M. Teresa De Martino,
• Loai K. E. A. Abdelmohsen,
• Floris P. J. T. Rutjes and
• Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

• representation of a Pickering emulsion with the enzyme in the water phase (i), or with the enzyme inside the polymersome lumen (ii). 3b) Chart of the specific activities of CalB dissolved in the water phase of the polymersome Pickering emulsion (left), CalB in a biphasic water/toluene system (middle,) and CalB

• encapsulated in the lumen of the polymersome Pickering emulsion (right). Adapted with permission from [79]. Cross-linked polymersomes with Cu(OTf)2 catalyst. Reprinted with permission from [15]. Schematic representation of enzymatic polymerization in polymersomes. (A) CALB in the aqueous compartment (B) CALB

• embedded in the bilayer. Reprinted with permission from [21]. Copyright 2007 American Chemical Society. Representation of DSN-G0. Reprinted with permission from [100]. The multivalent esterase dendrimer 5 catalyzes the hydrolysis of 8-acyloxypyrene 1,3,6-trisulfonates 6a–c. Reprinted with permission from

Enhanced quantum yields by sterically demanding aryl-substituted β-diketonate ancillary ligands

• Rebecca Pittkowski and
• Thomas Strassner

Beilstein J. Org. Chem. 2018, 14, 664–671, doi:10.3762/bjoc.14.54

• ); 195Pt NMR (CDCl3, 64.52 MHz) δ (ppm) −3383; ESIMS m/z = 688.4 [M + H]+; anal. calcd for C33H36N2O2Pt: C, 57.63; H, 5.28; N, 4.07; found: C, 57.93; H, 5.46; N, 3.82. ORTEP representation of 3. Thermal ellipsoids are drawn at the 50% probability level. Selected bond lengths (Å) and angles (deg): C(1)–Pt(1

High-yielding continuous-flow synthesis of antimalarial drug hydroxychloroquine

• Eric Yu,
• Hari P. R. Mangunuru,
• Nakul S. Telang,
• Caleb J. Kong,
• Jenson Verghese,
• Stanley E. Gilliland III,
• Saeed Ahmad,
• Raymond N. Dominey and
• B. Frank Gupton

Beilstein J. Org. Chem. 2018, 14, 583–592, doi:10.3762/bjoc.14.45

• were obtained in accordance with those previously reported [38][39]. Commercially available antimalarial drugs. Current batch syntheses of the key intermediate 5-(ethyl(2-hydroxyethyl)amino)pentan-2-one (6). Retrosynthetic strategy to hydroxychloroquine (1). Schematic representation for continuous in

• -line extraction of 10. Optimization of the flow process for the synthesis of 12. Optimization of the flow process for the synthesis of 10. Schematic representation for the continuous telescoped process to synthesize 11. Optimization of the flow process for the reductive amination of 12 using a CSTR

Latest development in the synthesis of ursodeoxycholic acid (UDCA): a critical review

• Fabio Tonin and
• Isabel W. C. E. Arends

Beilstein J. Org. Chem. 2018, 14, 470–483, doi:10.3762/bjoc.14.33

• dehydroxylation reactions are highlighted with a red, blue and green arrow, respectively. Names of compounds are indicated in the box. The general stereoinformation of steroid scaffold is shown in Figure 2. R = 4-pentanoic acid. Schematic representation of the flow reactor for the continuous conversion of CDCA to

Terahertz spectroscopy of 2,4,6-trinitrotoluene molecular solids from first principles

• Ido Azuri,
• Anna Hirsch,
• Anthony M. Reilly,
• Alexandre Tkatchenko,
• Shai Kendler,
• Oded Hod and
• Leeor Kronik

Beilstein J. Org. Chem. 2018, 14, 381–388, doi:10.3762/bjoc.14.26

• experimental and computed peaks denote peak assignment. Schematic representation of typical TNT vibrational modes, demonstrated using modes of the orthorhombic polymorph at frequencies of (a) ca. 1.0 THz, (b) ca. 2.3 THz. Purple and orange arrows denote the direction of primary inter- and intramolecular

Continuous-flow retro-Diels–Alder reaction: an efficient method for the preparation of pyrimidinone derivatives

• Imane Nekkaa,
• Márta Palkó,
• István M. Mándity and
• Ferenc Fülöp

Beilstein J. Org. Chem. 2018, 14, 318–324, doi:10.3762/bjoc.14.20

• were selected on the basis of the solubility of the starting materials. A schematic representation of the flow reactor setup is illustrated in Figure 1. Products 9–14 thus prepared were identified by means of HPLC–MS and NMR spectroscopic analysis. All physical and spectroscopic data of pyrimidinones 9

Polarization spectroscopy methods in the determination of interactions of small molecules with nucleic acids – tutorial

• Tamara Šmidlehner,
• Ivo Piantanida and
• Gennaro Pescitelli

Beilstein J. Org. Chem. 2018, 14, 84–105, doi:10.3762/bjoc.14.5

Aminosugar-based immunomodulator lipid A: synthetic approaches

• Alla Zamyatina

Beilstein J. Org. Chem. 2018, 14, 25–53, doi:10.3762/bjoc.14.3

Recent applications of click chemistry for the functionalization of gold nanoparticles and their conversion to glyco-gold nanoparticles

• Vivek Poonthiyil,
• Thisbe K. Lindhorst,
• Vladimir B. Golovko and
• Antony J. Fairbanks

Beilstein J. Org. Chem. 2018, 14, 11–24, doi:10.3762/bjoc.14.2

• derivatives, DCM, 11000 atm, 25 °C, 15–24 h [48]. The synthesis of AuNPs functionalized with strained alkyne derivatives. HBTU = O-benzotriazole-N,N,N',N'-tetramethyluroniumhexafluorophosphate; DIPEA = N,N-diisopropylethylamine [57]. A schematic representation of the SPAAC between azide-functionalized

Halogen-containing thiazole orange analogues – new fluorogenic DNA stains

• Aleksey A. Vasilev,
• Meglena I. Kandinska,
• Stanimir S. Stoyanov,
• Stanislava B. Yordanova,
• David Sucunza,
• Juan J. Vaquero,
• Obis D. Castaño,
• Stanislav Baluschev and
• Silvia E. Angelova

Beilstein J. Org. Chem. 2017, 13, 2902–2914, doi:10.3762/bjoc.13.283

• and in the presence of increasing concentrations of dsDNA (c = 0–1.4 × 10−4 M). Photostability of dyes TO-7Cl and 5a–d in acetonitrile in the concentration range of 1 × 10−5 M. B3LYP optimized structures. Graphical representation of the frontier orbitals (isodensity plot, isovalue = 0.02 a.u

Synthetic mRNA capping

• Fabian Muttach,
• Nils Muthmann and
• Andrea Rentmeister

Beilstein J. Org. Chem. 2017, 13, 2819–2832, doi:10.3762/bjoc.13.274

• mRNA caps which conferred specific properties such as eIF4E binding and turned non-modified RNAs into strongly eIF4E-binding RNAs. Schematic representation of enzymatic 5′-cap formation in eukaryotic mRNA. The 5′-triphosphate-end of the pre-mRNA is hydrolyzed to a diphosphate by an RNA 5

• nucleotide results in formation of the cap1 structure. Nucleotide analogues 1–11 were converted by Paramecium bursaria Chlorella virus-1 capping enzyme instead of GTP to generate RNAs with the respective caps [45]. Schematic representation of co-transcriptional capping with different cap analogues. A DNA

Metal-mediated base pairs in parallel-stranded DNA

• Jens Müller

Beilstein J. Org. Chem. 2017, 13, 2671–2681, doi:10.3762/bjoc.13.265

• ) Reversed Hoogsteen-type A:T and G:CH+ base pairs. R, R’, R’’ = DNA backbone. Representation of a β-dA:α-dT base pair. Representation of mononuclear metal-mediated base pairs involving canonical pyrimidine nucleobases. Base pairs within an antiparallel-stranded context are displayed in grey, whereas base

Synthesis, effect of substituents on the regiochemistry and equilibrium studies of tetrazolo[1,5-a]pyrimidine/2-azidopyrimidines

• Elisandra Scapin,
• Paulo R. S. Salbego,
• Caroline R. Bender,
• Alexandre R. Meyer,
• Anderson B. Pagliari,
• Tainára Orlando,
• Geórgia C. Zimmer,
• Clarissa P. Frizzo,
• Helio G. Bonacorso,
• Nilo Zanatta and
• Marcos A. P. Martins

Beilstein J. Org. Chem. 2017, 13, 2396–2407, doi:10.3762/bjoc.13.237

• [1,5-a]pyrimidine observed in solution (CDCl3 and DMSO-d6) and 2-azidopyrimidine observed in the solid state based on equilibrium. ORTEP® [45] plot of 8i with thermal ellipsoids drawn at 50% probability level. Representation of the possible equilibrium existing between 6i, 7i, and 8i. Reaction

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

• Martina Tireli,
• Silvija Maračić,
• Stipe Lukin,
• Marina Juribašić Kulcsár,
• Dijana Žilić,
• Mario Cetina,
• Ivan Halasz,
• Silvana Raić-Malić and
• Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

• gray. c) Capped-stick representation of 5, showing the dimer formed by C–H∙∙∙N hydrogen bond (orange stippled lines). Synthetic procedures for preparation of p-halogen-substituted and non-substituted phenyl-1,2,3-triazole 6-phenyl-2-(trifluoromethyl)quinolines. Reaction conditions and yields for the

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

• . Measurements were conducted at the steady-state of inhibition, occurring at 20 min of incubation. Structural representation of fisetin as guest (a) and γ-CD as host (b) used in the present study, depicting the herein adopted labeling for atoms and rings of fisetin. Selected FTIR bands for fisetin and its

Novel approach to hydroxy-group-containing porous organic polymers from bisphenol A

• Tao Wang,
• Yan-Chao Zhao,
• Li-Min Zhang,
• Yi Cui,
• Chang-Shan Zhang and
• Bao-Hang Han

Beilstein J. Org. Chem. 2017, 13, 2131–2137, doi:10.3762/bjoc.13.211

• (downtriangle), PPOP-2 (circle), and PPOP-3 (square) (a) hydrogen at 77 K, (b) carbon dioxide at 273 K, (c) carbon dioxide at 298 K, and (d) methane at 273 K. Variation of isosteric heat of adsorption with amount of adsorbed CO2 in PPOP-1, PPOP-2, and PPOP-3. Schematic representation of the possible structures

β-Cyclodextrin- and adamantyl-substituted poly(acrylate) self-assembling aqueous networks designed for controlled complexation and release of small molecules

• Liang Yan,
• Duc-Truc Pham,
• Philip Clements,
• Stephen F. Lincoln,
• Jie Wang,
• Xuhong Guo and
• Christopher J. Easton

Beilstein J. Org. Chem. 2017, 13, 1879–1892, doi:10.3762/bjoc.13.183

• = 100%. Representation of ditopic complexation of an ADddn substituent of PAAADddn, by two β-CDen substituents of PAAβ-CDen through initial complexation of the adamantyl group followed by complexation of the dodecyl linker in the sequence (a) to (b) to (c). 2D NOESY 1H NMR spectrum of 0.44 wt % PAAβ

• MR, MO, or EO at 298.2 K in aqueous Na2HPO4/KH2PO4 buffer at pH 7.0 and I = 0.10 mol dm−3. In each system, the concentrations of the β-CDen and adamantyl substituents were 3.60 × 10−3 mol dm−3 and 1.20 × 10−3 mol dm−3, respectively, and the dye concentration was 2.00 × 10−3 mol dm−3. Representation

Selective enzymatic esterification of lignin model compounds in the ball mill

• Ulla Weißbach,
• Saumya Dabral,
• Laure Konnert,
• Carsten Bolm and
• José G. Hernández

Beilstein J. Org. Chem. 2017, 13, 1788–1795, doi:10.3762/bjoc.13.173

• mixture was recovered from the milling jar, supported on silica gel and the product was purified by silica column chromatography. (a) Molecular representation of lignin. (b) Lignin model compound erythro-1a. Enzymatic reactions under ball milling conditions. Chemical and enzymatic esterification of

Molecular recognition of N-acetyltryptophan enantiomers by β-cyclodextrin

• Spyros D. Chatziefthimiou,
• Mario Inclán,
• Petros Giastas,
• Athanasios Papakyriakou,
• Konstantina Yannakopoulou and
• Irene M. Mavridis

Beilstein J. Org. Chem. 2017, 13, 1572–1582, doi:10.3762/bjoc.13.157

• H8; (b) the few differences observed in the intermolecular interactions have been magnified and reflect somewhat different binding modes of the two enantiomers revealed by intermolecular interactions of guest protons H8 and H4 only; (c) schematic representation of the respective solution models for

Chemical systems, chemical contiguity and the emergence of life

• Terrence P. Kee and
• Pierre-Alain Monnard

Beilstein J. Org. Chem. 2017, 13, 1551–1563, doi:10.3762/bjoc.13.155

• then be able to perform an increasingly more complex chemistry. These systems are precursors of protocells that preceded the emergence of ancestral cells. (B) Putative representation of a protocell (adapted from [3]). Independently of the type of chemicals involved, e.g., pure RNA catalysts/”genetic

Grip on complexity in chemical reaction networks

• Albert S. Y. Wong and
• Wilhelm T. S. Huck

Beilstein J. Org. Chem. 2017, 13, 1486–1497, doi:10.3762/bjoc.13.147

• network motif based on autocatalytic production and delayed inhibition of an enzyme that was kept out-of-equilibrium. (d) Schematic representation of the flow reactor that is used to implement flow. (e) The output of the reactor was measured using an enzymatic activity in an offline analysis. The response