Clustering and curation of electropherograms: an efficient method for analyzing large cohorts of capillary electrophoresis glycomic profiles for bioprocessing operations

• Ian Walsh,
• Matthew S. F. Choo,
• Sim Lyn Chiin,
• Amelia Mak,
• Shi Jie Tay,
• Pauline M. Rudd,
• Yang Yuansheng,
• Andre Choo,
• Ho Ying Swan and
• Terry Nguyen-Khuong

Beilstein J. Org. Chem. 2020, 16, 2087–2099, doi:10.3762/bjoc.16.176

• . This can be caused by a combination of sample complexity, temperature, pH, day of analysis, and other physicochemical fluctuations during the operation of the analysis. Although GU calculation can help solve this for the qualitative analysis, there is still difficulty automating peak picking due to

How and why plants and human N-glycans are different: Insight from molecular dynamics into the “glycoblocks” architecture of complex carbohydrates

• Carl A. Fogarty,
• Aoife M. Harbison,
• Amy R. Dugdale and
• Elisa Fadda

Beilstein J. Org. Chem. 2020, 16, 2046–2056, doi:10.3762/bjoc.16.171

• invoked when discussing other biopolymers or complex carbohydrates. In the specific case of glycans, the structural complexity, in terms of the diversity of monosaccharides, the linkages’ stereochemistry and the branched scaffolds, makes the already difficult case even more intricate. Nevertheless, the

• , the functionalization of the arms to include terminal β(1-3)-Gal reduces the occurrence of this event down to around 5%, see Table S6 in Supporting Information File 1. Terminal LeA and LeX motifs in plant N-glycans: To understand how an increased complexity on the arms would affect the dynamics of the

Polarity effects in 4-fluoro- and 4-(trifluoromethyl)prolines

• Vladimir Kubyshkin

Beilstein J. Org. Chem. 2020, 16, 1837–1852, doi:10.3762/bjoc.16.151

• . Nonetheless, it is barely conclusive to approach interaction of complex molecules with solvents using net dipole alone. For example, even for the relatively simple molecules like 1–4, the net dipole would not adequately represent neither the complexity of the interaction network within the molecule, nor

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

• Lucas Guillemard and
• Joanna Wencel-Delord

Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147

• routes to afford molecular complexity from simple precursors, while concomitantly limiting the number of steps and waste generation. Following this general key objective, the landscape of organic synthesis has been clearly changed by the development of ecofriendly methodologies such as metal-catalyzed C

• motif, have also attracted significant scientific interest [103]. Such couplings allowed constructing molecular complexity from very simple arenes such as benzene, toluene or mesitylene. However, such transformations frequently required rather harsh reaction conditions as well as the addition of strong

Synthesis of Streptococcus pneumoniae serotype 9V oligosaccharide antigens

• Sharavathi G. Parameswarappa,
• Claney L. Pereira and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2020, 16, 1693–1699, doi:10.3762/bjoc.16.140

• escape the host immune response [1][7]. These polysaccharides of SP consist of repeating units (RU) that range from di- to heptasaccharides that may be branched and/or charged [8]. Modifications such as O-acetylation, phosphorylation, and sulfation further increase CPS complexity. Many bacterial

A dynamic combinatorial library for biomimetic recognition of dipeptides in water

• Florian Klepel and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2020, 16, 1588–1595, doi:10.3762/bjoc.16.131

• compounds could not be achieved due to the high complexity of the library and the structural similarity of its members. Hence ESI-TOF mass spectrometry data can be interpreted qualitatively but not quantitatively. A full reference sample is shown in Figure 1. Each chromatogram represents a single

Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides

• Mateo Berton,
• Kevin Sheehan,
• Andrea Adamo and
• D. Tyler McQuade

Beilstein J. Org. Chem. 2020, 16, 1343–1356, doi:10.3762/bjoc.16.115

• ]. These systems are designed to achieve a generality of operation, and this comes with an increase in the cost and complexity of the instruments. Our on-demand approach targets the opposite end of the equipment design spectrum; it requires a low-cost systems designed to carry out only a few specific

• functions in a safe and robust manner. It also demands to be low-cost in order to have any potential for real-world applications. In other words, to achieve the set goals, innovation is needed to reduce the complexity/expense of (1) pumps; (2) reactors; (3) valves; (4) fittings, and (5) chemical containers

Highly selective Diels–Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole

• Carlos H. Escalante,
• Eder I. Martínez-Mora,
• Carlos Espinoza-Hicks,
• Alejandro A. Camacho-Dávila,
• Fernando R. Ramos-Morales,
• Francisco Delgado and
• Joaquín Tamariz

Beilstein J. Org. Chem. 2020, 16, 1320–1334, doi:10.3762/bjoc.16.113

• with the complexity of its structures [11][19][20][21][22][23][24][25][26][27]. The intramolecular Heck arylation coupling reaction is among the most useful strategies for the construction of these compounds (Scheme 1) [11][21]. For example, isoindolo[2,1-a]indoles 6 have been prepared by the

Oxime radicals: generation, properties and application in organic synthesis

• Igor B. Krylov,
• Stanislav A. Paveliev,
• Alexander S. Budnikov and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2020, 16, 1234–1276, doi:10.3762/bjoc.16.107

• , arylalkyl, and diaryl oxime radicals was also studied by EPR spectroscopy [53]. Radicals were generated under inert atmosphere directly in the EPR cavity by photolysis of the added di-tert-butyl peroxide (Scheme 1). The authors pointed out the complexity of the processes of iminoxyl radicals’ decomposition

A smart deoxyribozyme-based fluorescent sensor for in vitro detection of androgen receptor mRNA

• Ekaterina A. Bryushkova,
• Erik R. Gandalipov and
• Julia V. Nuzhina

Beilstein J. Org. Chem. 2020, 16, 1135–1141, doi:10.3762/bjoc.16.100

• types of compounds. It is most promising to develop simple and effective biosensors for the use in situations where traditional methods are not available due to their complexity and laboriousness. In this project, a novel smart deoxyribozyme-based fluorescent sensor for the detection of androgen

A simple and easy to perform synthetic route to functionalized thienyl bicyclo[3.2.1]octadienes

• Dragana Vuk,
• Irena Škorić,
• Valentina Milašinović,
• Krešimir Molčanov and
• Željko Marinić

Beilstein J. Org. Chem. 2020, 16, 1092–1099, doi:10.3762/bjoc.16.96

• numerous biologically active natural compounds (Figure 1) [4][5][6][7], their strenuous isolation procedures from plants, as well as their complicated multistage synthesis due to the complexity of their structure, encouraged us to develop a simple one-step synthetic procedure based on a photochemical

Synthesis of new asparagine-based glycopeptides for future scanning tunneling microscopy investigations

• Laura Sršan and
• Thomas Ziegler

Beilstein J. Org. Chem. 2020, 16, 888–894, doi:10.3762/bjoc.16.80

• complexity of the aforementioned macromolecules caused by PTM still constitutes a technical challenge. They can only be applied to small amounts of pure material, which is insufficient for extended biological investigations [4][6]. Hitherto, a variety of glycopeptides are used for medicinal applications, for

Diversity-oriented synthesis of 17-spirosteroids

• Benjamin Laroche,
• Thomas Bouvarel,
• Martin Louis-Sylvestre and
• Bastien Nay

Beilstein J. Org. Chem. 2020, 16, 880–887, doi:10.3762/bjoc.16.79

• their characteristic 3D geometry [68]. In particular, with 17-spirosteroids [69][70][71][72][73][74][75][76], the three dimensional complexity of the steroid CD-ring system is expected to be substantially affected. Results and Discussion The first goal of this work aimed at synthesizing spirocyclic

Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules

• Valerian Dragutan,
• Ileana Dragutan,
• Albert Demonceau and
• Lionel Delaude

Beilstein J. Org. Chem. 2020, 16, 738–755, doi:10.3762/bjoc.16.68

• complexity, by essentially using a Ru-catalyzed alkene–alkyne (Ru-AA) coupling reaction and a macrolactonization step (Scheme 8). In this carefully designed total synthesis, after applying a Marshall coupling reaction aimed at installing a propargyl group into the initial acetylene component, an enyne

• other memory impairments, namely (−)-galanthamine (13), has attracted great interest for its structural complexity and specific bioactivity. The total synthesis of compound 13, described by Brown et al. [81], involved an enyne ring-closing metathesis and a Heck cross-coupling as the key reactions for

• , hydroxylation, etc. This point of view has allowed to master a concise access to the target products which require exceptional chemical and stereochemical complexity. The excellence of the Grubbs- and Schrock-type metathesis catalysts as selective and proficient promoters of enyne metathesis was emphasized. The

Recent advances in Cu-catalyzed C(sp³)–Si and C(sp³)–B bond formation

• Balaram S. Takale,
• Ruchita R. Thakore,
• Elham Etemadi-Davan and
• Bruce H. Lipshutz

Beilstein J. Org. Chem. 2020, 16, 691–737, doi:10.3762/bjoc.16.67

• alcohol due to decomposition. Nonetheless, several products could be transformed into molecules of greater complexity. For example, cyclopropanation could be achieved to give 269. Additionally, TBS protection of 268 followed by ring closing metathesis (RCM) led to the interesting 6-membered silacycle 270

Synthesis of organic liquid crystals containing selectively fluorinated cyclopropanes

• Zeguo Fang,
• Nawaf Al-Maharik,
• Peer Kirsch,
• Matthias Bremer,
• Alexandra M. Z. Slawin and
• David O’Hagan

Beilstein J. Org. Chem. 2020, 16, 674–680, doi:10.3762/bjoc.16.65

• ], but the complexity of their synthesis has limited their development as practical materials. As a consequence, it continues to be a research objective to introduce polar substituents in a manner that can influence the nature of the dielectric anisotropy of the resultant material. In this context we

Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment

• Jan Geldsetzer and
• Markus Kalesse

Beilstein J. Org. Chem. 2020, 16, 670–673, doi:10.3762/bjoc.16.64

• investigations on the construction of the segments 3 and 4 as well as our results on the cross coupling between both fragments. Our retrosynthetic approach (Figure 1) divides chondrochloren A (1) into three fragments of similar complexity: amide 2, (Z)-bromide 4 and amide 3. For the coupling of amide 3 and (Z

Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles

• Ming-Xi Bi,
• Shuai Liu,
• Yangen Huang,
• Xiu-Hua Xu and
• Feng-Ling Qing

Beilstein J. Org. Chem. 2020, 16, 657–662, doi:10.3762/bjoc.16.62

• construction of compounds with structural diversity and complexity. In 2014, Wang reported the first radical cascade trifluoromethylthiolation and cyclization of activated alkenes (Scheme 1a) [23]. Afterward, Nevado [24], Hopkinson and Glorius [25], Dagousset and Magnier [26], as well as Fu [27] applied this

Opening up connectivity between documents, structures and bioactivity

• Christopher Southan

Beilstein J. Org. Chem. 2020, 16, 596–606, doi:10.3762/bjoc.16.54

• seems that way). The following is a selection: 1.) PubChem presents users with the complexity of parallel systems of D-C connectivity [28]. For medical subject headings (MeSH) the publication links are biased towards common name matches in many papers (e.g., the MeSH category for chemicals and drugs

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

Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors

• Delphine Pichon,
• Jennifer Morvan,
• Christophe Crévisy and
• Marc Mauduit

Beilstein J. Org. Chem. 2020, 16, 212–232, doi:10.3762/bjoc.16.24

• accomplished in this stimulating field. Keywords: acylimidazole; N-acyloxazolidinone; N-acylpyrrole; N-acylpyrrolidinone; aldehyde; amide; copper catalysis; electron-deficient alkenes; enantioselective conjugate addition; Michael acceptor; thioester; Introduction Generating high molecular complexity and

Combination of multicomponent KA² and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones

• Riccardo Innocenti,
• Elena Lenci,
• Gloria Menchi and
• Andrea Trabocchi

Beilstein J. Org. Chem. 2020, 16, 200–211, doi:10.3762/bjoc.16.23

• generate the maximum diversity and complexity from simple starting materials applying divergent synthetic strategies, such as the use of complexity-generating reactions and the build/couple/pair approach [17][18]. The application of multicomponent approaches has proven to be very useful as starting points

• , ring complexity) into single dimensional numerical values (principal components), to simplify the comparison with different sets of compounds. ChemGPS-NP [62][63][64] was chosen for the PCA analysis, providing a comprehensive exploration of the chemical space in terms of global mapping onto a

• 3–39 possess lower tendency to stay in the rod side of the triangle, as compared to BB drugs, suggesting for these compounds a higher shape complexity, as due to the presence of quaternary carbon atoms introduced by the KA2 coupling reaction. The intramolecular Pauson–Khand cyclization proved to be

Potent hemithioindigo-based antimitotics photocontrol the microtubule cytoskeleton in cellulo

• Alexander Sailer,
• Franziska Ermer,
• Yvonne Kraus,
• Rebekkah Bingham,
• Ferdinand H. Lutter,
• Julia Ahlfeld and
• Oliver Thorn-Seshold

Beilstein J. Org. Chem. 2020, 16, 125–134, doi:10.3762/bjoc.16.14

• development beyond classical small molecule inhibitors; since the spatiotemporal complexity inherent to the diversity of tubulin-dependent cellular processes may finally yield to studies that can leverage high-spatiotemporal-specificity optical control to deliver cell-specific, time-reversible modulation of

Starazo triple switches – synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes

• Andreas H. Heindl and
• Hermann A. Wegner

Beilstein J. Org. Chem. 2020, 16, 22–31, doi:10.3762/bjoc.16.4

• allow to drastically increase the information storage capacity and complexity of smart materials. In this context, unsymmetrical 1,3,5-tris(arylazo)benzenes – ‘starazos’ – which merge three photoswitches on one benzene ring, were successfully prepared. Two different synthetic strategies, one based on

Terpenes

• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2019, 15, 2966–2967, doi:10.3762/bjoc.15.292

• products. Their remarkable structural complexity and diversity is a result of a unique biosynthetic pathway invented by nature that starts with the formation of only a few acyclic precursors termed oligoprenyl diphosphates. These precursors containing multiple olefinic double bonds can be ionised to