Synthesis of new pyrrole–pyridine-based ligands using an in situ Suzuki coupling method

• Matthias Böttger,
• Björn Wiegmann,
• Steffen Schaumburg,
• Peter G. Jones,
• Wolfgang Kowalsky and
• Hans-Hermann Johannes

Beilstein J. Org. Chem. 2012, 8, 1037–1047, doi:10.3762/bjoc.8.116

• …N configurations are trans for the bipyridyl substructure (N–C–C–N torsion angle −155.8(1)°) but cis for the pyrrolylpyridine substructure (torsion angle 3.8(2)°). The former is well-known as a structural preference of 2,2'-bipyridyl systems. A search of the Cambridge Structural Database [16] for

The use of glycoinformatics in glycochemistry

• Thomas Lütteke

Beilstein J. Org. Chem. 2012, 8, 915–929, doi:10.3762/bjoc.8.104

• graphically within the publication figures. And even when information on glycan chains is given in the text, the notation is often complex, difficult to parse, and may contain ambiguities. Therefore, database users should keep in mind that if a database does not list any reference that, e.g., deals with the

• synthesis of a specific glycan structure, it does not mean that there is no such reference available: it just might not have been included into the database yet. Aside from providing literature references, carbohydrate databases can also serve glycochemists as a source of information on structures that are

• literature, was the Complex Carbohydrate Structure Database (CCSDB) [19], which is often referred to by the name of its querying software, CarbBank [20]. Each CarbBank entry contains a glycan structure together with a bibliographic reference, and further information such as taxonomic data of the biological

Mutational analysis of a phenazine biosynthetic gene cluster in Streptomyces anulatus 9663

• Orwah Saleh,
• Katrin Flinspach,
• Lucia Westrich,
• Andreas Kulik,
• Bertolt Gust,
• Hans-Peter Fiedler and
• Lutz Heide

Beilstein J. Org. Chem. 2012, 8, 501–513, doi:10.3762/bjoc.8.57

• prenyltransferase gene ppzP and, downstream thereof, the genes of the mevalonate pathway for supply of the isoprenoid precursor dimethylallyl diphosphate (DMAPP). Upstream of ppzP, four genes, orf1-orf4, could be identified. Database comparisons by using BLAST and Pfam searches gave no obvious clues as to whether

Syntheses and applications of furanyl-functionalised 2,2’:6’,2’’-terpyridines

• Jérôme Husson and
• Michael Knorr

Beilstein J. Org. Chem. 2012, 8, 379–389, doi:10.3762/bjoc.8.41

• Cambridge Structural Database reveals that more than 600 complexes have been structurally characterised, with the number rapidly growing. Because of all these interesting features and properties, these compounds find widespread applications in biomedical sciences [4][5], for photovoltaic applications [6][7

Fifty years of oxacalix[3]arenes: A review

• Kevin Cottet,
• Paula M. Marcos and
• Peter J. Cragg

Beilstein J. Org. Chem. 2012, 8, 201–226, doi:10.3762/bjoc.8.22

(How) does 1,3,5-triethylbenzene scaffolding work? Analyzing the abilities of 1,3,5-triethylbenzene- and 1,3,5-trimethylbenzene-based scaffolds to preorganize the binding elements of supramolecular hosts and to improve binding of targets

• Xing Wang and
• Fraser Hof

Beilstein J. Org. Chem. 2012, 8, 1–10, doi:10.3762/bjoc.8.1

• the unsubstituted analogues. By studying experimental data from the literature and the Cambridge Structural Database, as well as by conducting computational studies of representative structures, we concluded that the steric gearing offered by the ethyl groups confers some energetic advantage over the

• Database, as well as with computational analysis of some representative host systems. We hope that these simple computational approaches might be more broadly useful for predicting the behavior of new supramolecular hosts. Results and Discussion Literature binding affinities Chelating ligand 2Et, the

• from no difference to a 17-fold difference, with an average ∆∆G of 0.4 kcal/mol in favor of ethyl substitution. Crystallographic analysis of conformations We next carried out a survey of the literature data in the Cambridge Structure Database to evaluate the conformations adopted by 1,3,5

Meta-metallation of N,N-dimethylaniline: Contrasting direct sodium-mediated zincation with indirect sodiation-dialkylzinc co-complexation

• David R. Armstrong,
• Liam Balloch,
• Eva Hevia,
• Alan R. Kennedy,
• Robert E. Mulvey,
• Charles T. O'Hara and
• Stuart D. Robertson

Beilstein J. Org. Chem. 2011, 7, 1234–1248, doi:10.3762/bjoc.7.144

• Structural Database [36] found that the bisaryl model has precedent in alkali-metal zincate chemistry, for example, the previously prepared biscarboxamide ((TMEDA)Li{2-(1-C(O)N(i-Pr)2)C6H4}2Zn(t-Bu)) [37], however the donor ability of the different directing groups limits comparison with 4. A salient feature

Design and synthesis of a cyclitol-derived scaffold with axial pyridyl appendages and its encapsulation of the silver(I) cation

• Pierre-Marc Léo,
• Christophe Morin and
• Christian Philouze

Beilstein J. Org. Chem. 2010, 6, 1022–1024, doi:10.3762/bjoc.6.115

• : Synthesis and characterisation data for compounds 1–9 and 1·Ag(I). Acknowledgements The help of Corinne Bailly (CDC-Cambridge database searching), Catherine Belle (spectrophotometry), Béatrice Gennaro (low-temperature NMR experiments) and Guy Serratrice (spectrophotometry) is gratefully acknowledged.

Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane

• Bruno Linclau,
• Leo Leung,
• Jean Nonnenmacher and
• Graham Tizzard

Beilstein J. Org. Chem. 2010, 6, No. 62, doi:10.3762/bjoc.6.62

• about the crystallographic 41 screw axes. Thus the crystal structure comprises of alternating left and right handed hydrogen bonded helical constructs with each molecule part of two adjacent helices (Figure 5). Examination of the Cambridge Structural Database [49] (V5.31, November 2009) revealed three

Anion receptors containing thiazine-1,1-dioxide heterocycles as hydrogen bond donors

• Hong-Bo Wang,
• James A. Wisner and
• Michael C. Jennings

Beilstein J. Org. Chem. 2010, 6, No. 50, doi:10.3762/bjoc.6.50

• 1 and 3 circumscribe a very similar meridian. In fact, we manipulated the single crystal molecular structures of 1 and the 4,4′-di-t-butyl derivative of 3 [30] (available from the Cambridge Crystallographic Database #1003/6124) by rotating the two relevant dihedral angles to bring the NH groups into

The subtle balance of weak supramolecular interactions: The hierarchy of halogen and hydrogen bonds in haloanilinium and halopyridinium salts

• Kari Raatikainen,
• Massimo Cametti and
• Kari Rissanen

Beilstein J. Org. Chem. 2010, 6, No. 4, doi:10.3762/bjoc.6.4

• by extracting some relevant crystal structures: 4-BrPhNH3Cl (2, CCDC ref. code TAWRAL), 4-ClPhNH3Cl (3, CURGOL), 4-FPhNH3Cl (4, ANLCLA), 4-BrPhNH3H2PO4, (7, UGISEI), 3-BrPyHCl, (11, CIHBAX) and 3-ClPyHCl, (12, VOQMUJ) from Cambridge Structural Database for sake of comparison. Based on the X-ray data

• existence of the short interaction distance between the halogen atom and a nucleophilic atom in a number of crystal structures [5][6]. In 1996 Allen and co-workers [7] did an extensive statistical analysis of all of the crystal structures in the Cambridge Structural Database (CSD) for carbon-bound halogen

Ring-alkyl connecting group effect on mesogenic properties of p-carborane derivatives and their hydrocarbon analogues

• Aleksandra Jankowiak,
• Piotr Kaszynski,
• William R. Tilford,
• Kiminori Ohta,
• Adam Januszko,
• Takashi Nagamine and
• Yasuyuki Endo

Beilstein J. Org. Chem. 2009, 5, No. 83, doi:10.3762/bjoc.5.83

• quadrupole moments. Therefore, compounds containing these fragments would be expected to exhibit both similar and high mesophase stability. The data show otherwise and a large difference in TC is observed for the isomeric esters (e.g. for 19B/20B ΔTNI = 80 K; for other examples see LiqCryst database [50

Functional properties of metallomesogens modulated by molecular and supramolecular exotic arrangements

• Alessandra Crispini,
• Mauro Ghedini and
• Daniela Pucci

Beilstein J. Org. Chem. 2009, 5, No. 54, doi:10.3762/bjoc.5.54

• number of metal-containing liquid crystals, already synthesized and analysed with respect to their chemical and physical properties, can constitute a huge database for the design of new biologically relevant complexes. Review Palladium(II) complexes New mononuclear ortho-palladated complexes have been

Inversion symmetry and local vs. dispersive interactions in the nucleation of hydrogen bonded cyclic n-mer and tape of imidazolecarboxamidines

• Sihui Long,
• Venkatraj Muthusamy,
• Peter G. Willis,
• Sean Parkin and
• Arthur Cammers

Beilstein J. Org. Chem. 2008, 4, No. 23, doi:10.3762/bjoc.4.23

• packing: 83% of the entries in the Cambridge Structural Database that do not symmetry-relate molecules possess pseudosymmetry within 0.5 Å [26]. Molecules capable of either chiral or achiral space groups prefer the latter with concomitant minimization of Z'. The infrequency of chiral space groups in the

Trifluoromethyl ethers – synthesis and properties of an unusual substituent

• Frédéric R. Leroux,
• Baptiste Manteau,
• Jean-Pierre Vors and
• Sergiy Pazenok

Beilstein J. Org. Chem. 2008, 4, No. 13, doi:10.3762/bjoc.4.13

• without ortho substituents in the Cambridge Structural Database, found that none of the entries has the –OCF3 group in the plane of the phenyl ring (Figure 4). From six compounds, five entries have a dihedral angle C-C-O-C of around 90° and one compound showed a skew conformation (dihedral angle C=C/OCF3

The vicinal difluoro motif: The synthesis and conformation of erythro- and threo- diastereoisomers of 1,2-difluorodiphenylethanes, 2,3-difluorosuccinic acids and their derivatives

• David O'Hagan,
• Henry S. Rzepa,
• Martin Schüler and
• Alexandra M. Z. Slawin

Beilstein J. Org. Chem. 2006, 2, No. 19, doi:10.1186/1860-5397-2-19

• tool for influencing the conformation of performance organic molecules and particularly tuning conformation by selecting specific diastereoisomers (erythro or threo). Background Of the 298,876 registered fluorinated structures in the Beilstein Chemical Database (for 2005) only 279 compounds contain a

Colchitaxel, a coupled compound made from microtubule inhibitors colchicine and paclitaxel

• Karunananda Bombuwala,
• Thomas Kinstle,
• Vladimir Popik,
• Sonal O. Uppal,
• James B. Olesen,
• Jose Viña and
• Carol A. Heckman

Beilstein J. Org. Chem. 2006, 2, No. 13, doi:10.1186/1860-5397-2-13

• classification methods, we showed that cells could be classified by reference to a database of known normal and cancerous cell phenotypes. Promoters caused loss of properties specific to normal cells and gain of properties of cancer cells. Other compounds, including colchicine, had a similar effect. Colchicine

• inhibitors and their combination. Methods of quantifying these endpoints are lacking, so that, with few exceptions comparisons must be based upon qualitative data. The laboratory's classification procedure addresses this deficiency, as it allows phenotypes created in an experiment to be related to a database

Trapping evidence for the thermal cyclization of di-(o-acetylphenyl)acetylene to 3,3'-dimethyl- 1,1'-biisobenzofuran

• Charles P. Casey,
• Neil A. Strotman and
• Ilia A. Guzei

Beilstein J. Org. Chem. 2005, 1, No. 18, doi:10.1186/1860-5397-1-18

• data for all new compounds and X-ray crystallographic data for meso-3 (16 pages). X-ray crystallographic data for meso-3 has been deposited in the Cambridge Structural Database (CCDC # 289103). X-ray crystal structure of meso-3. Thermal cyclization of η2-(o-ethynylbenzoyl)rhenium complexes to rhenium

Molecular recognition. 1. Crystal structures of hexaazamacrocyclic amines containing p-xylylene spacers and their adducts with acids

• Teresa Borowiak,
• Grzegorz Dutkiewicz,
• Maciej Kubicki,
• Marek Pietraszkiewicz,
• Agnieszka Gil and
• Rainer Mattes

Beilstein J. Org. Chem. 2005, 1, No. 16, doi:10.1186/1860-5397-1-16

• different anions. However, structural information on the complexes of 1 with anions is scarce in the Cambridge Database.[12] Only two types of protonation of 1 have been found so far. With the very weak acid – o-nitrophenol 1 forms a tetra-protonated salt whereas with hydrochloric or hydrobromic acids a