Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

• Serge Pérez and
• Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

• , the double helices have a radial orientation, and are perpendicular to the surface of the granule. At the resolution of these ultra-structural features (10 µm) there is no discontinuity of orientation, i.e., no disclination of orientation. Between 10 µm steps, the change of the direction of the double

Cyclodextrins tethered with oligolactides – green synthesis and structural assessment

• Cristian Peptu,
• Mihaela Balan-Porcarasu,
• Alena Šišková,
• Ľudovít Škultéty and
• Jaroslav Mosnáček

Beilstein J. Org. Chem. 2017, 13, 779–792, doi:10.3762/bjoc.13.77

• characterization should be performed in order to fully describe such systems. We showed that understanding of molecular level structural features of such complex mixtures (free CDs, homopolymers, CD-oligoesters) have to take into consideration the mass spectrometry methods in direct correlation with the NMR

Inclusion complexes of β-cyclodextrin with tricyclic drugs: an X-ray diffraction, NMR and molecular dynamics study

• Franca Castiglione,
• Fabio Ganazzoli,
• Luciana Malpezzi,
• Andrea Mele,
• Walter Panzeri and
• Giuseppina Raffaini

Beilstein J. Org. Chem. 2017, 13, 714–719, doi:10.3762/bjoc.13.70

• , consistent with the 1:1 host–guest stoichiometry. Some important structural features of the inclusion complexes of 1 and 2 can be outlined by the analysis of the 1H NMR spectra: the spectrum of 1 shows that the AB quartet assigned to H9–H10 spin system is split into two AB quartets on passing from pure 1 to

• compound 1. Compounds 1 and 2 are not planar and the exocyclic double bond prevents the free rotation of the side chain with respect to the ring system. Consequently, 1 and 2 show inherent chirality [9] as lacking of symmetry elements. The main purpose of the work is the comparison of the structural

• features obtained in the solid state and in D2O solution by X-ray diffraction and NMR spectroscopy, respectively. The dynamic behaviour of the examined systems is simulated by MD runs of the complexes with explicit water. Suitable structural descriptors thus obtained as time averages are then compared to

Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia)

• Alexander Bogdanov,
• Cora Hertzer,
• Stefan Kehraus,
• Samuel Nietzer,
• Sven Rohde,
• Peter J. Schupp,
• Heike Wägele and
• Gabriele M. König

Beilstein J. Org. Chem. 2017, 13, 502–519, doi:10.3762/bjoc.13.50

• 1H,1H spin system required heteronuclear long range correlations for the elucidation of the remaining structural features and the closure of the cembrane ring. Methylene group CH2-3 exhibited HMBC correlations with resonances of the keto at C-2, sp2 quaternary carbon C-4 and tertiary carbon C-5 and

Structure–efficiency relationships of cyclodextrin scavengers in the hydrolytic degradation of organophosphorus compounds

• Sophie Letort,
• Michaël Bosco,
• Benedetta Cornelio,
• Frédérique Brégier,
• Sébastien Daulon,
• Géraldine Gouhier and
• François Estour

Beilstein J. Org. Chem. 2017, 13, 417–427, doi:10.3762/bjoc.13.45

• pesticides and soman was evaluated. Some structural features of the scavengers could be identified as the key elements in charge to accelerate the decontamination of organophosphorus compounds: (1) the degradation kinetics of organophosphorus constituents is dependent on their affinity for the cyclodextrin

Efficient access to β-vinylporphyrin derivatives via palladium cross coupling of β-bromoporphyrins with N-tosylhydrazones

• Vinicius R. Campos,
• Ana T. P. C. Gomes,
• Anna C. Cunha,
• Maria da Graça P. M. S. Neves,
• Vitor F. Ferreira and
• José A. S. Cavaleiro

Beilstein J. Org. Chem. 2017, 13, 195–202, doi:10.3762/bjoc.13.22

• diversity of structural features that can be induced in the porphyrin structure [14][15][16]. Alkenyl-type moieties are examples of versatile functional groups which are present in several biologically active natural porphyrin derivatives or are substituents that can be introduced into the macrocycles

Dynamics and interactions of ibuprofen in cyclodextrin nanosponges by solid-state NMR spectroscopy

• Monica Ferro,
• Franca Castiglione,
• Nadia Pastori,
• Carlo Punta,
• Lucio Melone,
• Walter Panzeri,
• Barbara Rossi,
• Francesco Trotta and
• Andrea Mele

Beilstein J. Org. Chem. 2017, 13, 182–194, doi:10.3762/bjoc.13.21

• on passing from the empty CDNS to the drug-loaded CDNS, thus showing that the drug encapsulation can be seen as the formation of a real supramolecular aggregate rather than a conglomerate of two solid components. Finally, the structural features obtained from the different solid-state NMR approaches

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

• structural features are examined and enantiomeric differentiation obtained with P-CDs is compared to prior results acquired with CM-CDs. Results and Discussion Thirty-three substrates including α-methylbenzylamine (1), N,α-dimethylbenzylamine (2), N,N-dimethyl-1-phenethylamine (3), N-allyl-α

Supramolecular frameworks based on [60]fullerene hexakisadducts

• Andreas Kraft,
• Johannes Stangl,
• Ana-Maria Krause,
• Klaus Müller-Buschbaum and
• Florian Beuerle

Beilstein J. Org. Chem. 2017, 13, 1–9, doi:10.3762/bjoc.13.1

• the spacer length, the solvent-filled pore systems in the solid-state structures have been tuned and structural features such as porosity of the materials have been investigated by PXRD, TGA analysis and sorption studies. Results and Discussion Recently, we reported on the synthesis and solid-state

Synthesis of acylhydrazino-peptomers, a new class of peptidomimetics, by consecutive Ugi and hydrazino-Ugi reactions

• Angélica de Fátima S. Barreto,
• Veronica Alves dos Santos and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2016, 12, 2865–2872, doi:10.3762/bjoc.12.285

• allows an easy access to highly functionalized peptomers in good yields and a reduced number of steps. This method may also be employed to obtain new classes of peptidomimetics with potential biological activity. Structural features of (a) peptide, (b) peptoid, (c) peptomer, (d) azapeptide, (e

New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation

• Pavel Nagorny and
• Zhankui Sun

Beilstein J. Org. Chem. 2016, 12, 2834–2848, doi:10.3762/bjoc.12.283

• attempting to elucidate the nature of halogen complexes have emerged since then; however, the structural features of these interactions were unclear until the work of Mulliken who proposed the formation of donor–acceptor complexes [65][66] and Odd Hassel who conducted crystallographic studies of bromine

Computational methods in drug discovery

• Sumudu P. Leelananda and
• Steffen Lindert

Beilstein J. Org. Chem. 2016, 12, 2694–2718, doi:10.3762/bjoc.12.267

Enzymatic synthesis and phosphorolysis of 4(2)-thioxo- and 6(5)-azapyrimidine nucleosides by E. coli nucleoside phosphorylases

• Vladimir A. Stepchenko,
• Anatoly I. Miroshnikov,
• Frank Seela and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2016, 12, 2588–2601, doi:10.3762/bjoc.12.254

• 2.4.2.4) phosphorylases [36], and (ii) the role of structural features and electronic properties of the pyrimidine bases and nucleosides in the recognition by E. coli nucleoside phosphorylases. Results and Discussion Thioxo- and 6-aza-pyrimidines used in the transglycosylation reaction with recombinant E

• -deoxyribosides. Unexpectedly, 2-thiouridine (9) showed weak activity for PNP whereas 2-thiothymidine (11b) entirely was lacking such an activity. It is conceivable that in the case of such unusual substrates of PNP as pyrimidine nucleosides their structural features define the substrate properties, viz., 2

Synthesis, dynamic NMR characterization and XRD studies of novel N,N’-substituted piperazines for bioorthogonal labeling

• Constantin Mamat,
• Marc Pretze,
• Matthew Gott and
• Martin Köckerling

Beilstein J. Org. Chem. 2016, 12, 2478–2489, doi:10.3762/bjoc.12.242

• superimposed figure of the two conformers, where C1, the phenyl ring and F1 of both conformers are fitted on top of each other. The different structural arrangement of both conformers is clearly visible. Similar structural features are observed for 3a. The N1–C1 atom distance is again much shorter, 1.346(2) Å

Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia

• Artem N. Semakin,
• Aleksandr O. Kokuev,
• Yulia V. Nelyubina,
• Alexey Yu. Sukhorukov,
• Petr A. Zhmurov,
• Sema L. Ioffe and
• Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2016, 12, 2471–2477, doi:10.3762/bjoc.12.241

• modulation of the molecular geometry, for example through coordination with metal cations, hydrogen bond formation or irradiation. These unique structural features of the hydrazone fragment have been successfully exploited in the design of various molecular switches, fluorophores and machines. Bis- and

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

• Ze’en Xiao,
• Senhua Chen,
• Runlin Cai,
• Shao’e Lin,
• Kui Hong and
• Zhigang She

Beilstein J. Org. Chem. 2016, 12, 2077–2085, doi:10.3762/bjoc.12.196

• , respectively. In addition, compounds 1 and 3 exhibited weak radical scavenging activity with EC50 values of 125 and 138 μM, respectively. Keywords: α-glucosidase; Aspergillus; DPPH·; furoisocoumarin; isocoumarin; Introduction Isocoumarins are an important group of natural products with diverse structural

• features and interesting biological activities. They have been widely isolated from fungi, lichens, bacteria, plants, and insects [1][2]. Furoisocoumarins combining a furan ring and an isocoumarin moiety are divided into two subclasses depending on their fusion type: linear furo[2,3-g]isocoumarins and

Synthesis of the C8’-epimeric thymine pyranosyl amino acid core of amipurimycin

• Pramod R. Markad,
• Navanath Kumbhar and
• Dilip D. Dhavale

Beilstein J. Org. Chem. 2016, 12, 1765–1771, doi:10.3762/bjoc.12.165

• ; carbohydrate; peptidyl nucleosides; Introduction Peptidyl nucleoside antibiotics are a class of complex molecules that encompass an extensive array of natural products [1]. The notable structural features of peptidyl nucleosides are responsible for their miscellaneous biological activities such as antitumor

Synthesis and characterization of benzodithiophene and benzotriazole-based polymers for photovoltaic applications

• Desta Gedefaw,
• Marta Tessarolo,
• Margherita Bolognesi,
• Mario Prosa,
• Renee Kroon,
• Wenliu Zhuang,
• Patrik Henriksson,
• Kim Bini,
• Ergang Wang,
• Michele Muccini,
• Mirko Seri and
• Mats R. Andersson

Beilstein J. Org. Chem. 2016, 12, 1629–1637, doi:10.3762/bjoc.12.160

• donor:acceptor intermixing combined with finely ordered and aggregated polymeric domains, in perfect agreement with the improved photovoltaic performance. This better self-organization of the PTzBDT-2:PC61BM blend seems in contrast with the intrinsic structural features of the polymer, where the double alkyl

Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity

• Atul A. Dhavan,
• Rahul D. Kaduskar,
• Loana Musso,
• Leonardo Scaglioni,
• Piera Anna Martino and
• Sabrina Dallavalle

Beilstein J. Org. Chem. 2016, 12, 1624–1628, doi:10.3762/bjoc.12.159

• ]. Chemical analysis of a terrestrial-derived Streptomyces sp. isolated from the rhizosphere of the plant Juniperus excelsa yielded a new metabolite, leopolic acid A (1, Figure 1) [2]. Leopolic acid has unprecedented structural features consisting of an aliphatic side chain attached to a 2,3-pyrrolidinedione

• before, we decided to incorporate the structural features found in leopolic acid into this novel heterocyclic system. Accordingly, Wittig olefination of 14, followed by coupling with L-phenylalanine benzyl ester, and subsequent catalytic hydrogenation in EtOAc of 16 afforded the analogue of leopolic acid

Beta-hydroxyphosphonate ribonucleoside analogues derived from 4-substituted-1,2,3-triazoles as IMP/GMP mimics: synthesis and biological evaluation

• Tai Nguyen Van,
• Audrey Hospital,
• Corinne Lionne,
• Lars P. Jordheim,
• Charles Dumontet,
• Christian Périgaud,
• Laurent Chaloin and
• Suzanne Peyrottes

Beilstein J. Org. Chem. 2016, 12, 1476–1486, doi:10.3762/bjoc.12.144

• (cN-II), an enzyme involved in the regulation of purine nucleotide pools. NMR and molecular modelling studies showed that a few derivatives adopted similar structural features to IMP or GMP. Five derivatives were identified as modest inhibitors with 53 to 64% of cN-II inhibition at 1 mM. Keywords

Modular synthesis of the pyrimidine core of the manzacidins by divergent Tsuji–Trost coupling

• Sebastian Bretzke,
• Stephan Scheeff,
• Felicitas Vollmeyer,
• Friederike Eberhagen,
• Frank Rominger and
• Dirk Menche

Beilstein J. Org. Chem. 2016, 12, 1111–1121, doi:10.3762/bjoc.12.107

• -metathesis of a challenging homoallylic urea substrate, which proceeds in good yields in the presence of an organic phosphoric acid. Keywords: cross-metathesis; natural products; pyrimidines; Tsuji–Trost reaction; synthetic methods; Introduction Chiral pyrimidine motifs constitute prevalent structural

• features in a variety of potent natural products and bioactive agents [1][2][3][4][5]. As exemplified by the marine natural products manzazidins A and C [2][3][4][5], they may be characterized by diverse configurations, including synthetically challenging quaternary centers. Owing to their pronounced

Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update

• Bin Yu,
• Hui Xing,
• De-Quan Yu and
• Hong-Min Liu

Beilstein J. Org. Chem. 2016, 12, 1000–1039, doi:10.3762/bjoc.12.98

Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents

• Daniel Wiegmann,
• Stefan Koppermann,
• Marius Wirth,
• Giuliana Niro,
• Kristin Leyerer and
• Christian Ducho

Beilstein J. Org. Chem. 2016, 12, 769–795, doi:10.3762/bjoc.12.77

• [22]. The naturally occurring muraymycins isolated from Streptomyces guided first insights into the structural features essential for MraY inhibition. For the most active member of the family, i.e., muraymycin A1, antibiotic activity could be found against various bacteria ranging from Staphylococci

From steroids to aqueous supramolecular chemistry: an autobiographical career review

• Bruce C. Gibb

Beilstein J. Org. Chem. 2016, 12, 684–701, doi:10.3762/bjoc.12.69

• specific orientations [19][20][21]. Beyond these structural features, the biggest determinant in guest binding was the solvent. Solvents such as DMSO gave the strongest complexations, whilst halogenated solvents gave the weakest. Apparently the former does not solvate the cavity well. One of the remarkable

Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• be discussed. Review 1 Occurrence and activities In this chapter special sub-types of α-pyrones will be described. The compounds are grouped into three categories depending on their structural features: (i) dibenzo-α-pyrones, (ii) monocyclic α-pyrones, and (iii) monobenzo-α-pyrones. 1.1 Dibenzo-α