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

• complex 62, which bears a thiocyanato group at the para-position (Scheme 11). Because of the presence of a thiocyanato moiety in its structural motif and due to its fluorescence properties, compound 62 could be used potentially as a labelling agent for biomolecules. In fact, reaction between the reactive

• . In all the examples cited above, furanyl-functionalised terpyridines were selected because of their capability to absorb light and to transfer the excitation energy to the chelated lanthanide metal ion. This gives rise to a strong fluorescence, a feature which is required for labelling studies

• -functionalised tpys as potential biomolecule-labelling agents. Synthetic sequence envisioned for biomolecules labelling by click-chemistry. Influence of solvent on U/S ratio. Complexes obtained by direct oxidation of furanyl-functionalised tpys. GI50 (μg/ml) for terpyridines 12 and 13 compared to doxorubicin

Novel fatty acid methyl esters from the actinomycete Micromonospora aurantiaca

• Jeroen S. Dickschat,
• Hilke Bruns and
• Ramona Riclea

Beilstein J. Org. Chem. 2011, 7, 1697–1712, doi:10.3762/bjoc.7.200

• isopropyl group (m/z = 43 and m/z =143) shifted to m/z = 50 and m/z = 145 in agreement with the deuterium labelling of this portion of the molecule. The labelling was also introduced into the iso-odd FAMEs 102 and 103 (Figures S3C to S3F of Supporting Information File 1) and the higher homologue methyl 15

• -methylhexadecanoate (not shown). Methyl 15-methylhexadecanoate was only found during feeding of [2H10]leucine, similar to the formation of methyl 14-methylhexadecanoate found only during feeding of [2H10]isoleucine. Feeding of [2H8]valine Feeding of [2H8]valine resulted in the incorporation of the isotopic labelling

• genome of M. aurantiaca, but the pathway seemed not to be active under the experimental conditions, judged by the fact that no incorporation of [2H8]valine into the iso-odd FAMEs was observed. Furthermore, no uptake of labelling from [2H10]leucine into the iso-even FAMEs was found, which also rules out a

Synthesis of dye/fluorescent functionalized dendrons based on cyclotriphosphazene

• Aurélien Hameau,
• Sabine Fuchs,
• Régis Laurent,
• Jean-Pierre Majoral and
• Anne-Marie Caminade

Beilstein J. Org. Chem. 2011, 7, 1577–1583, doi:10.3762/bjoc.7.186

• interesting for elaboration of the original dendrimeric architectures [13][14], or for labelling materials or biological entities. In many cases, it is desirable to concentrate a maximum number of functional groups in a small compound (a small size is particularly important so as not to disturb biological

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

• ]+ calcd for C8H9I2N, 372.8; found, 373.8. Molecular structure of 2 with selective atom labelling. Hydrogen atoms and minor disorder components are omitted for clarity [20]. Molecular structure of 3 with selective atom labelling and thermal ellipsoids drawn at the 50% probability level. Hydrogen atoms are

• ). Molecular structure of 4 with selective atom labelling and thermal ellipsoids drawn at the 50% probability level. Hydrogen atoms and disordered component of TMEDA are omitted for clarity. Secondary contacts between sodium and the anilide rings are denoted by dashed lines. Only one of the

Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines

• Paul W. Davies,
• Nicolas Martin and
• Neil Spencer

Beilstein J. Org. Chem. 2011, 7, 839–846, doi:10.3762/bjoc.7.96

• Paul W. Davies Nicolas Martin Neil Spencer School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, United Kingdom 10.3762/bjoc.7.96 Abstract Isotopic labelling studies were performed to probe a proposed 1,2-aryl shift in the gold-catalysed cycloisomerisation of alkynyl

• aziridines into 2,4-disubstituted pyrroles. Two isotopomers of the expected skeletal rearrangement product were identified using 13C-labelling and led to a revised mechanism featuring two distinct skeletal rearrangements. The mechanistic proposal has been rationalised against the reaction of a range of 13C

• - and deuterium-labelled substrates. Keywords: 1,2-aryl shift; cycloisomerisation; gold; isotopic labelling; pyrrole; skeletal rearrangement; Introduction Gold-catalysed cycloisomerisation reactions have emerged as powerful methods to construct a diverse array of hetero- and carbocyclic motifs under

High chemoselectivity in the phenol synthesis

• Matthias Rudolph,
• Melissa Q. McCreery,
• Wolfgang Frey and
• A. Stephen K. Hashmi

Beilstein J. Org. Chem. 2011, 7, 794–801, doi:10.3762/bjoc.7.90

• , and these could even be trapped by Diels–Alder reactions. In addition, labelling studies were carried out and the electronic influence of substituents was investigated [21]. Computational studies as well as side-products produced in the reaction pointed towards intermediates A and B (Scheme 1) [22][23

Bioorthogonal metabolic glycoengineering of human larynx carcinoma (HEp-2) cells targeting sialic acid

• Arne Homann,
• Riaz-ul Qamar,
• Sevnur Serim,
• Petra Dersch and
• Jürgen Seibel

Beilstein J. Org. Chem. 2010, 6, No. 24, doi:10.3762/bjoc.6.24

• )neuraminic acid (Neu5Hex) into the cell-surface glycocalyx of a human larynx carcinoma cell line (HEp-2) and its fluorescence labelling by click chemistry. Keywords: bioorthogonal metabolic glycoengineering; click chemistry; sialic acid; Introduction The surface of eukaryotic cells is heavily covered with

• (Scheme 2). Metabolic glycoengineering of human larynx carcinoma (HEp-2) cells by incorporation of N-(1-oxohex-5-ynyl)neuraminic acid (Neu5Hex, 3) The metabolic labelling of human larynx carcinoma (HEp-2) cell surfaces was carried out in order to study and characterize the influence of sialic acid in cell

• ester, azido-fluorescein (14). For the metabolic labelling of eukaryotic cells, HEp-2 cells were incubated in Dulbecco's modified Eagle's medium (DMEM) with 10% fetal calf serum (FCS). At 80% confluence they were split into 6-well plates with DMEM containing the functionalized carbohydrates (Ac4GlcNAz

A convenient method for preparing rigid-core ionic liquid crystals

• Julien Fouchet,
• Laurent Douce,
• Benoît Heinrich,
• Richard Welter and
• Alain Louati

Beilstein J. Org. Chem. 2009, 5, No. 51, doi:10.3762/bjoc.5.51

• view of compound 1a with partial labelling. The closest molecules are represented (with lower opacity) when connected by CH-π and/or non classical H-bonds (black thin lines). The ellipsoids enclose 50% of the electronic density. Symmetry operators for equivalent positions: d = ±1+x, y, z; e = 1+x, 1+y

Themed series in organo- fluorine chemistry

• David O'Hagan

Beilstein J. Org. Chem. 2008, 4, No. 11, doi:10.3762/bjoc.4.11

• the area of medical imaging, positron emission tomography (PET) has undergone a step change in growth across all developing countries, with an exponential increase in the installation of PET cameras and cyclotrons to generate isotope for labelling ligands and diagnostic probes. 18F is an important