Volatiles from three genome sequenced fungi from the genus Aspergillus

• Jeroen S. Dickschat,
• Ersin Celik and
• Nelson L. Brock

Beilstein J. Org. Chem. 2018, 14, 900–910, doi:10.3762/bjoc.14.77

• the penny bun (Boletus edulis) [7], but can also inhibit the growth of other fungi [8] which likely contributes to the induction of systemic resistance in plants by Trichoderma [9]. Fungal volatiles can also act as self-inhibitors of fungal germination [10] or as attractants for insects involved in

Volatiles from the xylarialean fungus Hypoxylon invadens

• Jeroen S. Dickschat,
• Tao Wang and
• Marc Stadler

Beilstein J. Org. Chem. 2018, 14, 734–746, doi:10.3762/bjoc.14.62

• (2), another widespread fungal volatile, a plant growth promoting effect and an induction of systemic resistance in plants against fungi was observed [5]. The significant biological effects of these and other fungal volatiles recently resulted in a considerable interest of natural product chemists

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

• of the malaria parasite Plasmodium falciparum. Hydroxychloroquine (1) is an antimalarial drug developed for both treatment and prevention of the disease in response to the widespread malaria resistance to chloroquine (2, Figure 1) [5][6]. Additionally, hydroxychloroquine (1, HCQ) is an effective non

Stimuli-responsive oligonucleotides in prodrug-based approaches for gene silencing

• Françoise Debart,
• Christelle Dupouy and
• Jean-Jacques Vasseur

Beilstein J. Org. Chem. 2018, 14, 436–469, doi:10.3762/bjoc.14.32

• such as gene regulation is to circumvent the poor chemical stability of nucleic acids in biological media due to their low resistance to nucleases and to overcome their low cell uptake due to their polyanionic nature. In the present review, we aimed to identify various ON prodrugs that are responsive

• the modified ONs in addition to an increase in their nuclease resistance. Thus, two Japanese groups have proposed prodrug-type phosphotriester ONs responsive to GSH (Scheme 1) [13][14]. Ono presented a preliminary study on a model of a thymidine dimer with differently substituted benzyl groups at the

• ’-F, 2’-OMe) have been proposed to increase the nuclease resistance of ONs, but most of them have decreased gene silencing potential. To overcome this drawback, novel prodrug-type RNAs containing a disulfide bridge at the 2’-position have been designed, and in 2016, Urata and our group reported on the

Recent developments in the asymmetric Reformatsky-type reaction

• Hélène Pellissier

Beilstein J. Org. Chem. 2018, 14, 325–344, doi:10.3762/bjoc.14.21

• constituted the key step of a nine-step total synthesis of the eastern fragment of jatrophane diterpene Pl-3, which is a complex natural product with high promising biological activities, such as antiproliferative activity and inhibition of the efflux-pump activity of multidrug resistance P-glycoprotein. The

Volatiles from the tropical ascomycete Daldinia clavata (Hypoxylaceae, Xylariales)

• Tao Wang,
• Kathrin I. Mohr,
• Marc Stadler and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2018, 14, 135–147, doi:10.3762/bjoc.14.9

• widespread fungal volatile is 6-pentyl-2H-pyran-2-one (2) that was first isolated from Trichoderma and exhibits a strong coconut aroma [5]. For fungi producing 2 a plant-growth promoting effect and an induction of systemic resistance in plants has been observed which makes these fungi interesting as

Aminosugar-based immunomodulator lipid A: synthetic approaches

• Alla Zamyatina

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

• to the phosphate groups of lipid A alters the TLR4-mediated host immunity and accounts for the modulation of the pro-inflammatory signaling. Additionally, this modification is associated with an amplified bacterial virulence since it confers resistance to the endogenous cationic antimicrobial

• ethanolamine that reduces the net negative charge and induces resistance to CAMPs (Figure 2). The unique structure of H. pylori lipid A plays a pivotal role in evading the host immune response by the bacterium [84]. Synthetically prepared structurally defined homogeneous H. pylori lipid A should help to

Position-dependent impact of hexafluoroleucine and trifluoroisoleucine on protease digestion

• Susanne Huhmann,
• Anne-Katrin Stegemann,
• Kristin Folmert,
• Damian Klemczak,
• Johann Moschner,
• Michelle Kube and
• Beate Koksch

Beilstein J. Org. Chem. 2017, 13, 2869–2882, doi:10.3762/bjoc.13.279

• proteolytic degradation in particular. Meng and Kumar reported that the incorporation of 5,5,5,5’,5’,5’-hexafluoroleucine (HfLeu) into the antimicrobial peptides magainin 2 amide and buforin enhanced their resistance towards proteolytic degradation by trypsin [23]. They also introduced HfLeu into the glucagon

• assay [30]. Substitution of tryptophan, tyrosine, and phenylalanine residues in a glycosylation-deficient mutant of Candida antarctica lipase B, CalB N74D, by their monofluorinated analogues, left the resistance to proteolytic degradation by proteinase K unchanged [31]. Incorporation of α-fluoroalkyl

• observed that the introduction of fluorine atoms into the Abu side chain can significantly improve or dramatically reduce resistance to hydrolysis by different enzymes and human blood plasma, depending upon the fluorine content of the side chain, the position of the substitution relative to the cleavage

Synthetic mRNA capping

• Fabian Muttach,
• Nils Muthmann and
• Andrea Rentmeister

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

• nuclease resistance – have been developed. Furthermore, cap analogues have therapeutic potential as demonstrated by a number of cap-derived translation inhibitors [61][62][63]. Applications of novel cap analogues The search for novel – non-natural or modified – caps with improved properties has already

• translation in in vitro translation experiments. In a further step, tetraphosphates with methylene(bisphosphonate) moieties were prepared which improved binding to eIF4E and in some cases conferred enzymatic resistance against DcpS degradation [67]. N2-Triazole-containing monophosphate cap analogues were

• structure and the exact positioning of the triazole linkage, modified cap analogues varied largely with regard to their functionality in in vitro translational assays, binding affinity to eIF4E and resistance to the decapping enzyme DcpS. Best translational efficiencies similar to the standard cap were

Binding abilities of polyaminocyclodextrins: polarimetric investigations and biological assays

• Marco Russo,
• Daniele La Corte,
• Annalisa Pisciotta,
• Serena Riela,
• Rosa Alduina and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2751–2763, doi:10.3762/bjoc.13.271

• resistance genes) and the emergence of multidrug resistant strains [59]. In addition, extracellular DNA has been shown to be important for biofilm establishment and maintenance by pathogenic bacteria, such as Pseudomonas aeruginosa and Staphylococcus aureus [60][61][62]. Some other bacteria, such as E. coli

• maintenance by pathogenic bacteria, such as P. aeruginosa and S. aureus [60][61][62]. In addition, eDNA with its negative charge can sequester cationic antibiotics contributing to antibiotic resistance; thus, removing eDNA from the biofilm matrix can weaken the biofilm and can raise its susceptibility to

• with E. coli and in vitro DNA manipulations were performed as described previously [66][67]. The pUC19 (ca. 2700 bp, conferring ampicillin resistance to E. coli) was extracted by alkaline lysis method [64]. Electrophoretic mobility shift assays (EMSA) of the pDNA were performed as described elsewhere

An efficient synthesis of 1,6-anhydro-N-acetylmuramic acid from N-acetylglucosamine

• Matthew B. Calvert,
• Christoph Mayer and
• Alexander Titz

Beilstein J. Org. Chem. 2017, 13, 2631–2636, doi:10.3762/bjoc.13.261

• in only five steps from the cheap starting material N-acetylglucosamine. This efficient synthesis should enable future studies into the importance of 1,6-anhydromuramic acid in bacterial cell wall recycling processes. Keywords: N-acetylmuramic acid; anhydrosugars; antibiotic resistance; bacterial

• cell wall recycling; carbohydrate synthesis; Introduction 1,6-Anhydro-N-acetylmuramic acid (AnhydroMurNAc, 1, Figure 1) and its derivatives (e.g., 2 and 3) are of great interest due to their integral role in bacterial cell wall recycling [1][2] and the induction of antibacterial resistance [3

Sulfation and amidinohydrolysis in the biosynthesis of giant linear polyenes

• Hui Hong,
• Markiyan Samborskyy,
• Katsiaryna Usachova,
• Katharina Schnatz and
• Peter F. Leadlay

Beilstein J. Org. Chem. 2017, 13, 2408–2415, doi:10.3762/bjoc.13.238

• . Sulfonation has been suggested as a novel approach to block the development of antibiotic resistance [33][34] while the discovery of the sulfated metabolite FR901379 was a critical breakthrough in the successful clinical development of micafungin to combat systemic fungal infections [12]. HPLC–UV–MS analysis

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• is small [21][22]. As a result, compounds into which fluorine has been introduced may show beneficial changes in their properties. In addition, among the chemical bonds formed by carbon, fluorine bonds have the highest binding energy [23], such that fluorine-containing compounds often show resistance

Phosphonic acid: preparation and applications

• Charlotte M. Sevrain,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

• anhydrase [37] or during the hydrolysis of amide [38]. The main difference between phosphate and phosphonic acid arises from the higher stability (resistance towards enzymatic degradation) of the P–C bond when compared to the P–O bond present in phosphate. Accordingly, phosphonic acid was used for numerous

1,3-Dibromo-5,5-dimethylhydantoin as promoter for glycosylations using thioglycosides

• Fei-Fei Xu,
• Claney L. Pereira and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2017, 13, 1994–1998, doi:10.3762/bjoc.13.195

• , including dichloromethane, is sold under the trade name Brom-55 and used as swimming pool sanitizer, as industrial brominating agent for ethylene propylene diene monomer rubber to improve ozone resistance, as additive in plastics to promote photodegradation and as a fungicide to preserve fresh fruits [27

Block copolymers from ionic liquids for the preparation of thin carbonaceous shells

• Sadaf Hanif,
• Bernd Oschmann,
• Dmitri Spetter,
• Muhammad Nawaz Tahir,
• Wolfgang Tremel and
• Rudolf Zentel

Beilstein J. Org. Chem. 2017, 13, 1693–1701, doi:10.3762/bjoc.13.163

• energy is needed to overcome the lattice energy and melt the salt. Ion liquids are also called “green solvents”, because of their low vapor pressure, fire resistance and thermal stability [4]. Beside this, they have a high ionic conductivity, large heat capacity and good thermal and chemical stability [5

Biomimetic molecular design tools that learn, evolve, and adapt

• David A Winkler

Beilstein J. Org. Chem. 2017, 13, 1288–1302, doi:10.3762/bjoc.13.125

• infections and drug resistant pathogens, and the increased use of implantable and indwelling medical devices. Much research is now focusing on developing materials that resist bacterial attachment and growth as an alternative to new antibacterial agents to which the development of resistance is inevitable

Total syntheses of the archazolids: an emerging class of novel anticancer drugs

• Stephan Scheeff and
• Dirk Menche

Beilstein J. Org. Chem. 2017, 13, 1085–1098, doi:10.3762/bjoc.13.108

• inhibition of V-ATPase abrogates tumor metastasis via repression of endocytic activation [28], leads to impaired cathepsin B activation in vivo [30], modulates anoikis resistance and metastasis of cancer cells [31], overcomes trastuzumab resistance of breast cancers [32], blocks iron metabolism and thereby

New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

• Maryna V. Murlykina,
• Maryna N. Kornet,
• Sergey M. Desenko,
• Svetlana V. Shishkina,
• Oleg V. Shishkin,
• Aleksander A. Brazhko,
• Vladimir I. Musatov,
• Erik V. Van der Eycken and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2017, 13, 1050–1063, doi:10.3762/bjoc.13.104

• of diseases. However, we are still facing the problem of untreated ones, together with the appearance of unknown disorders and the dramatical growth of antimicrobial resistance caused by the continuous evolution of microorganisms [1][2][3][4][5]. Therefore, there is urgency in careful screening the

• resistance to almost all the compounds tested in the given concentration range. The strain of B. subtilis was found to be sensitive to compounds 4i and 6d, but the bacteriostatic activity was fixed only in the highest concentration 500 mg/L. The information about the influence of the compounds on bacteria is

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• -antibiotic conjugates, were prepared and resulted able to overcome antibiotic resistance of microbial biofilms, since CA NPs render streptomycin more accessible to biofilms, thereby more available to interact with biofilm bacteria [89]. Similarly, a novel recyclable E.coli-specific killing GAuNP

Use of costic acid, a natural extract from Dittrichia viscosa, for the control of Varroa destructor, a parasite of the European honey bee

• Kalliopi Sofou,
• Demosthenis Isaakidis,
• Apostolos Spyros,
• Anita Büttner,
• Athanassios Giannis and
• Haralambos E. Katerinopoulos

Beilstein J. Org. Chem. 2017, 13, 952–959, doi:10.3762/bjoc.13.96

• ]. Literature data indicated that a number of pesticide residues have been detected in honey samples [11][12]. Given that the parasite has developed significant resistance to synthetic acaricides, alternatives such as oxalic acid [13][14][15] were proposed and extensively studied for their effects against

Molecular-level architectural design using benzothiadiazole-based polymers for photovoltaic applications

• Vinila N. Viswanathan,
• Arun D. Rao,
• Upendra K. Pandey,
• Arul Varman Kesavan and
• Praveen C. Ramamurthy

Beilstein J. Org. Chem. 2017, 13, 863–873, doi:10.3762/bjoc.13.87

• orbitals of polymer P2. Both the HOMO and LUMO levels of the polymer have decreased energy as compared to polymer P1 (from −5.48 eV to −5.53 eV and from −3.58 eV to −3.75 eV, respectively). This reduction of the HOMO energy level improves the resistance towards oxidative degradation of the material. Also

Continuous-flow processes for the catalytic partial hydrogenation reaction of alkynes

• Carmen Moreno-Marrodan,
• Francesca Liguori and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2017, 13, 734–754, doi:10.3762/bjoc.13.73

• issues owing to many potential side reactions, particularly in relation to chemoselectivity, i.e., over-hydrogenation of alkenes to alkanes [44][45], resistance of other functional groups (ketones [46][47], amines [48][49], azides [50]), regioselectivity [51][52] , isomerization [53][54] and

• ]; the strong metal–support interactions, particularly for inorganic oxide materials, e.g., TiO2 [94][95]. Besides contributing to catalyst resistance by hampering the loss and the size increase of active sites, MNP stabilization is a key factor to limit the amount of metal leached in solution, an issue

• selectivity issues, need of toxic additives, high metal loadings and limited catalyst resistance. Ever increasing environmental and economic constraints have boosted the development of innovative catalytic materials and processes with improved performance and lower environmental impact. Great advancements

Novel β-cyclodextrin–eosin conjugates

• Gábor Benkovics,
• Damien Afonso,
• András Darcsi,
• Szabolcs Béni,
• Sabrina Conoci,
• Éva Fenyvesi,
• Lajos Szente,
• Milo Malanga and
• Salvatore Sortino

Beilstein J. Org. Chem. 2017, 13, 543–551, doi:10.3762/bjoc.13.52

• ]. Singlet oxygen offers important advantages over conventional drugs as it: i) potentially attacks biological substrates of different nature (i.e., lipids, proteins, and DNA), ii) does not suffer from multidrug resistance (MDR) problems, and iii) due to its short half-life (<0.1 ms) and lack of charge, it

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

• : Excellent B1-field uniformity and B1/i field efficiency resulting in a high signal-to-noise ratio (SNR). In comparison to planar coils, the solenoid have lower resistance, better nutation curves (reaching the ideal sinusoidal behaviour) representing a much more uniform B1 field than planar coils, however

• planar coils are: Planar coils suffer of a high series resistance resulting in a low SNR as the latter is dominated by the thermal noise of the coil. The SNR depends on the geometrical features of the coil. For instance, the number of turns is crucial since a large number of turns can increase the

• unitary field produced by the coil but will also lead to higher resistance [21]. It is believed that the nearby windings of the coil induce static field distortions resulting in lower resolution and sensitivity in the NMR spectrum [22]. The optimum dimensions for a planar microcoil were presented by van