Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry

• Daniel Fürniss,
• Timo Mack,
• Frank Hahn,
• Sidonie B. L. Vollrath,
• Katarzyna Koroniak,
• Ute Schepers and
• Stefan Bräse

Beilstein J. Org. Chem. 2013, 9, 56–63, doi:10.3762/bjoc.9.7

• conjugation (Scheme 2) with minor modifications. The CuAAC was carried out by using Cu(CH3CN)4PF6 in THF with 2,6-lutidine as base. Only 1.60 equiv of the azidosugar were necessary to achieve full conversion after 18 h, and no shorter oligomers were observed in the MALDI–TOF spectrum. Cleavage from the resin

Synthesis of spiro[dihydropyridine-oxindoles] via three-component reaction of arylamine, isatin and cyclopentane-1,3-dione

• Yan Sun,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2013, 9, 8–14, doi:10.3762/bjoc.9.2

• spectra were obtained on a Bruker Tensor27 spectrometer (KBr disc). HRMS were measured on an AB 5800 MALDI–TOF/TOF instrument. X-ray data were collected on a Bruker Smart APEX-2 diffractometer. Typical procedure for the synthesis of spiro[dihydropyridine-oxindoles] 1a–1l from the three-component reaction

Influence of cyclodextrin on the solubility and the polymerization of (meth)acrylated Triton^® X-100

• Melanie Kemnitz and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 2176–2183, doi:10.3762/bjoc.8.245

• , matrix-assisted laser desorption ionization mass spectrometry (MALDI-TOF MS), dynamic light scattering (DLS), gel-permeation chromatography (GPC) and turbidity measurements. Additionally, the viscosity change of the methacrylic homopolymer with RAMEB-CD was evaluated. Keywords: (meth)acrylated Triton

• Hz, 4J = 2.18, 2H, aryl-CH), 6.13 (m, 1H, -CH3), 5.57 (m, 1H, =CH2), 4.29 (t, 3J = 4.86 Hz, 2H, -CH2-), 4.10 (t, 3J = 4.86 Hz, 2H, -CH2-), 3.64 (s, polyethoxy, 37H), 1.94 (t, 4J = 1.13 Hz, 4J = 1.33 Hz, 3H, =CH2), 1.69 (s, 2H, -CH2-), 1.33 (s, 6H, -(CH3)2), 0.70 (s, 9H, -(CH3)3); MALDI-TOF (CHCl3, n

• -), 1.32 (s, 6H, -(CH3)2), 0.69 (s, 9H, -(CH3)3); MALDI-TOF (CHCl3, n = number of ethoxy groups) m/z: 547 (n = 6), 591 (n = 7), 635 (n = 8), 679 (n = 9), 723 (n = 10), 767 (n = 11), 811 (n = 12), 855 (n = 13), 899 (n = 14), 943 (n = 15), 987 (n = 16), 1031 (n = 17), 1075 (n = 18), 1119 (n = 19

S-Fluorenylmethyl protection of the cysteine side chain upon N^α-Fmoc deprotection

• Johannes W. Wehner and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2012, 8, 2149–2155, doi:10.3762/bjoc.8.242

• glycoamino acid derivative 6 was not obtained. De-O-acetylation of 8 gave mannopyranoside 9 with maintained fluorenylmethyl protection at the sulfur atom. The structure of the S-Fm-protected glycoamino acid derivative 8 could be unequivocally confirmed by NMR analysis and MALDI–TOF mass spectrometry. The

• “Fmoc” refers to fluorenylmethoxycarbonyl and “Fm” to fluorenylmethyl. ESI mass spectra were recorded on a Mariner ESI-TOF 5280 (Applied Biosystems) instrument and MALDI-MS measurements on a MALDI-TOF-MS-Biflex III (Bruker) instrument by using 2,5-dihydroxybenzoic acid (DHB) or α-cyano-4-hydroxycinnamic

• -OCH2CH2), 66.1 (C-4), 62.4 (C-6), 54.0 (C-α), 46.9 (CH2-Fm), 38.7 (C-β), 38.6 (man-OCH2CH2), 36.4 (CH2-CHFm), 21.0, 20.9, 20.7, 20.7 (4 C(O)CH3) ppm; HRMS–ESI (m/z): calcd for C33H41N2O11S, 673.24; found, 673.21; MALDI–TOF–MS (CCA) m/z 673.73. S-(Fluoren-9-yl)-L-cysteine-[2-(α-D-mannopyranosyloxy)ethyl

Multivalent display of the antimicrobial peptides BP100 and BP143

• Imma Güell,
• Rafael Ferre,
• Kasper K. Sørensen,
• Esther Badosa,
• Iteng Ng-Choi,
• Emilio Montesinos,
• Eduard Bardají,
• Lidia Feliu,
• Knud J. Jensen and
• Marta Planas

Beilstein J. Org. Chem. 2012, 8, 2106–2117, doi:10.3762/bjoc.8.237

• (Bruker Daltonics). High-resolution mass spectrometry (HRMS) was recorded on a Bruker MicroToF-Q MALDI instrument by using a hybrid quadrupole time-of-flight mass spectrometer (University of Zaragoza). Circular dichroism (CD) measurements were obtained using a Jasco spectropolarimeter (J-810, Easton, MD

• +, 532.2 [M + 6H]6+; HRMS–MALDI (m/z): [M + Na]+ calcd for C156H264N36NaO30S2, 3208.9753; found, 3208.9737. Synthesis of carbopeptide (KKLfKKILKYL-C2H4N)2-cDTE (2) (4R,5S)-1,2-Dithiane-4,5-diyl bis(2-(Boc)2-Aoa) (cDTE) (4.8 mg, 6.9 μmol) was dissolved in TFA/CH2Cl2 (1:1, 1 mL) and stirred for 1 h. The

• 4.76) containing aniline (100 mM). The reaction mixture was stirred for 3 h and purified by preparative RP-HPLC using Method B (13.6 mg, 62% yield). HPLC: tR = 2.51 min (98% purity); ESIMS (m/z): 1594.1 [M + 2H]2+, 1063.5 [M + 3H]3+, 797.9 [M + 4H]4+, 638.4 [M + 5H]5+, 532.2 [M + 6H]6+; HRMS–MALDI (m/z

Chemical modification allows phallotoxins and amatoxins to be used as tools in cell biology

• Jan Anderl,
• Hartmut Echner and
• Heinz Faulstich

Beilstein J. Org. Chem. 2012, 8, 2072–2084, doi:10.3762/bjoc.8.233

• on Sephadex-LH20 with H2O/methanol (4:1) as solvent. Yield for Tat-phalloidin was 52%, for Arg8-phalloidin 43% and for Kaposi-peptide 39%. Purity of all conjugates was >90% as shown by HPLC (Table 1) and MALDI–TOF analysis. The HPLC analysis conditions were as follows: Column Knauer RP Nucleosil-100

• C18 (250 × 4 mm); mobile phase was a linear gradient of buffer A H2O, 0.05% TFA and buffer B acetonitrile/H2O (9:1), 0.05% TFA.; flow rate, 1.2 mL/min. General MALDI–TOF analysis was performed in the linear, high-mass, positive-ion mode with pulsed (time-delayed) extraction on a Kratos Maldi IV

Convergent synthesis of the tetrasaccharide repeating unit of the cell wall lipopolysaccharide of Escherichia coli O40

• Abhijit Sau and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2012, 8, 2053–2059, doi:10.3762/bjoc.8.230

• reference, unless stated otherwise. Chemical shift values are expressed in δ ppm. MALDI-MS were recorded on a Bruker Daltronics mass spectrometer. Commercially available grades of organic solvents of adequate purity were used in all reactions. HClO4–SiO2 was prepared following the method reported in the

• ), 50.8 (CH2N3), 20.7, 20.6, 20.5 (COCH3); MALDI-MS: 920.3 [M + Na]+; Anal. calcd for C48H55N3O14: C, 64.20; H, 6.17; found: C, 64.06; H, 6.35. 2-Azidoethyl O-(6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-D-mannopyranoside (8): A solution of compound 7 (1.8 g, 2.0 mmol

• ), 69.3 (C-6B), 68.5 (C-6A), 50.8 (CH2N3), 28.2, 26.4 (C(CH3)2); MALDI-MS: 834.3 [M + Na]+; Anal. calcd for C45H53N3O11: C, 66.57; H, 6.58; found: C, 66.42; H, 6.75. Ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-2-N-phthalimido-1-thio-β-D-glucopyranoside (9): To a

Dimerization of a cell-penetrating peptide leads to enhanced cellular uptake and drug delivery

• Jan Hoyer,
• Ulrich Schatzschneider,
• Michaela Schulz-Siegmund and
• Ines Neundorf

Beilstein J. Org. Chem. 2012, 8, 1788–1797, doi:10.3762/bjoc.8.204

• equiv of either Cym2 or Cbl, and activation with 4 equiv of HATU/DIPEA in DMF under vigorous shaking for 2 × 2 h. All peptides were purified by preparative reversed-phase HPLC using a binary eluent system consisting of 0.1% TFA in water and 0.08% TFA in acetonitrile and analyzed by MALDI or ESIMS, and

Synthesis of 5-oxyquinoline derivatives for reversal of multidrug resistance

• Torsten Dittrich,
• Nils Hanekop,
• Nacera Infed,
• Lutz Schmitt and
• Manfred Braun

Beilstein J. Org. Chem. 2012, 8, 1700–1704, doi:10.3762/bjoc.8.193

• spectroscopy was carried out on Bruker FT-ICR APEX III (7.0 T) (MALDI) at the University of Bielefeld. Column chromatography was performed with Fluka silica gel 60 (230–400 mesh), and thin-layer chromatography was carried out by using Merck TLC silicagel 60 F254 aluminium sheets. Toluene was freshly distilled

Antifreeze glycopeptide diastereomers

• Lilly Nagel,
• Carsten Budke,
• Axel Dreyer,
• Thomas Koop and
• Norbert Sewald

Beilstein J. Org. Chem. 2012, 8, 1657–1667, doi:10.3762/bjoc.8.190

• B. MALDI-TOF mass spectra were measured on a Voyager DE Instrument (PE Biosystems, Weiterstadt, Germany) mounted with a 1.2 m flight tube. 2,5-Dihydroxybenzoic acid was used as the matrix. Depending on the mass range the ions were accelerated at 15 to 25 kV with the option of detecting positive or

• Analytik GmbH – Magnetics, Karlsruhe, Germany), infinity cell, and interfaced to an external (nano)ESI or MALDI ion source. Scan accumulation and Fourier transformation were done with XMASS NT (7.08) on a PC workstation; for further data processing DataAnalysisTM 3.4 was used. Optical rotation was measured

• + 2Na]2+ 995.43429. H-[L-Ala-L-Ala-allo-L-Thr]4-L-Ala-L-Ala-OH (6, 2 mg, 2%): calcd for C46H80N14O19, 1133.21 (av.); found, 1132.572420 (monoisotopic); MS (MALDI-TOF) m/z: [M + Na]+ 1155.7; HRMS (ESI): [M + H]+ 1133.58309. H-[D-Ala-D-Ala-D-Thr(GalNAc)]4-D-Ala-D-Ala-OH (7, 10 mg, 5%): calcd for

Supramolecular hydrogels formed from poly(viologen) cross-linked with cyclodextrin dimers and their physical properties

• Yoshinori Takashima,
• Yang Yuting,
• Miyuki Otsubo,
• Hiroyasu Yamaguchi and
• Akira Harada

Beilstein J. Org. Chem. 2012, 8, 1594–1600, doi:10.3762/bjoc.8.182

• chromatography (elution: water–acetonitrile) to give α,α-CD dimer as a white solid in 22% yield. 1H NMR (DMSO-d6, 500 MHz) δ 8.36 (t, 2H, -NH), 7.88 (s, 4H, Ph), 5.59–5.40 (m, 24H, O(2,3)H of α-CD), 4.97–4.78 (m, 12H, C(1)H of α-CD), 4.55–4.41 (m, 10H, O(6)H of α-CD), 3.84–3.48 (m, C(3,6,5,3,4)H of α-CD); MALDI

• ); TLC: Rf 0.04 (n-butanol/ethanol/water 5:4:3); MALDI–TOF m/z: 2259 [M + Na]+. Preparation of β,β-dimer β,β-Dimer was prepared according to our previous report [25]. Preparation of viologen polymer (VP) 1,10-Dibromodecane (7.3 g, 24 mmol) was added to a solution of 4,4’-bipyridyl (4 g, 24 mmol) in DMSO

Influence of cyclodextrin on the solubility of a classically prepared 2-vinylcyclopropane macromonomer in aqueous solution

• Helmut Ritter,
• Jia Cheng and
• Monir Tabatabai

Beilstein J. Org. Chem. 2012, 8, 1528–1535, doi:10.3762/bjoc.8.173

• amino group at δ 2.85 ppm and the methylene protons adjacent to the thio group at δ 2.68 ppm which also confirms the structure of 3. The mass differences between the signals of the main series in MALDI-TOF MS correspond to the molar mass of the monomer NiPAAm units equal to 113 g/mol and the mass of end

• at 1 °C/min−1 in a magnetically stirred cell; values of the cloud points were defined as the temperature at which the deepest point of the derivative curve was achieved. MALDI-TOF MS was performed on a Bruker Ultraflex TDF mass spectrometer using a 337 nm nitrogen laser. GPC analyses were performed

• is flushed with nitrogen until it is colorless. Then, 4 mL of dimethyl sulfide (DMS) are added to the solution. The reaction mixture is stirred overnight at rt. Methanol is removed under reduced pressure. Mn = 1.8 × 104 g/mol, DI = 2.2; dn = 5.2 nm. MALDI-TOF MS of amino-terminated poly(NiPAAm) 3

Diarylethene-modified nucleotides for switching optical properties in DNA

• Sebastian Barrois and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2012, 8, 905–914, doi:10.3762/bjoc.8.103

• , 42.5, 38.5, 24.9, 15.0; MALDI–MS m/z (%): 633.6 (5) [M]+; HRMS–ESI (m/z): [M + H]+ calcd for C36H31N2O5S2, 635.1674; found, 635.1681. Compound 6: 15 (81 mg, 0.20 mmol), 5-iodo-2’-deoxyuridine (14, 140 mg, 0.40 mmol), dry NEt3 (30 µL, 0.40 mmol), Pd(PPh3)4 (46 mg, 0.04 mmol) and CuI (8 mg, 0.04 mmol

• 90 °C (10 min) followed by slow cooling to rt. MALDI–MS DNA1 m/z (%): 5898.9 (100) [M + DMT]−, 5597.3 (99) [M]−, 2949.2 (21) [M + DMT]−/2, 2797.7 (20) [M]2−/2; DNA2 m/z (%): 5950.0 (100) [M + DMT]−, 5647.9 (38) [M]−, 2974.6 (17) [M + DMT]2−/2, 2823.6 (7) [M]2−/2; DNA3 m/z (%): 5869.0 (100) [M + DMT

Formation of carbohydrate-functionalised polystyrene and glass slides and their analysis by MALDI-TOF MS

• Martin J. Weissenborn,
• Johannes W. Wehner,
• Christopher J. Gray,
• Robert Šardzík,
• Claire E. Eyers,
• Thisbe K. Lindhorst and
• Sabine L. Flitsch

Beilstein J. Org. Chem. 2012, 8, 753–762, doi:10.3762/bjoc.8.86

• analysed directly on these minimally conducting surfaces by MALDI-TOF mass spectrometry analysis after aluminium tape was attached to the underside of the slides. Furthermore, the trityl group appeared to act as an internal matrix and no additional matrix was necessary for the MS analysis. Thus, trityl

• groups can be used as simple hydrophobic, noncovalently linked anchors for ligands on surfaces and at the same time facilitate the in situ mass spectrometric analysis of such ligands. Keywords: carbohydrate array; conductive tape; MALDI-TOF MS; nonconductive surface; trityl-mediated adhesion

• , and have investigated the use of matrix-assisted laser desorption/ionisation time-of-flight (MALDI-TOF) mass spectrometry (MS) analysis (Figure 1B), which has been highly successful on ligands immobilised on gold plates [10]. MALDI-TOF MS requires an electrically conducting surface and a matrix for

Identification and isolation of insecticidal oxazoles from Pseudomonas spp.

• Florian Grundmann,
• Veronika Dill,
• Andrea Dowling,
• Aunchalee Thanwisai,
• Edna Bode,
• Narisara Chantratita,
• Richard ffrench-Constant and
• Helge B. Bode

Beilstein J. Org. Chem. 2012, 8, 749–752, doi:10.3762/bjoc.8.85

• its 16S-rRNA gene revealing it to be a Pseudomonas sp. with closest homology to P. putida (100% similarity: Supporting Information File 1, Figure S4) [11][12][13][14]. As judged on the basis of high-resolution MALDI–MS and LC–ESIMS/MS data the well-known entomopathogenic P. entomophila [15][16] also

Thiophene-based donor–acceptor co-oligomers by copper-catalyzed 1,3-dipolar cycloaddition

• Stefanie Potratz,
• Amaresh Mishra and
• Peter Bäuerle

Beilstein J. Org. Chem. 2012, 8, 683–692, doi:10.3762/bjoc.8.76

• ), d (doublet), t (triplet), m (multiplet). Mass spectra were measured at Finnigan MAT, SSQ 7000 by CI and Bruker Daltonics REFLEX III by MALDI-TOF. Elemental analysis for C, H and N were determined at Elementar Vario EL and for S at Carlo Erba 1104. High-resolution mass spectra were measured on a

Investigation of the network of preferred interactions in an artificial coiled-coil association using the peptide array technique

• Raheleh Rezaei Araghi,
• Carsten C. Mahrenholz,
• Rudolf Volkmer and
• Beate Koksch

Beilstein J. Org. Chem. 2012, 8, 640–649, doi:10.3762/bjoc.8.71

• -cyanocinnamic acid was used as a matrix for MALDI–TOF (Applied Biosystems, Forster City, USA) MS analysis. Binding studies on cellulose membranes [26]: All incubation and washing steps were carried out under gentle shaking and at room temperature. After washing of the membrane with ethanol once for 10 min and

Synthesis of szentiamide, a depsipeptide from entomopathogenic Xenorhabdus szentirmaii with activity against Plasmodium falciparum

• Friederike I. Nollmann,
• Andrea Dowling,
• Marcel Kaiser,
• Klaus Deckmann,
• Sabine Grösch,
• Richard ffrench-Constant and
• Helge B. Bode

Beilstein J. Org. Chem. 2012, 8, 528–533, doi:10.3762/bjoc.8.60

• protists in order to also understand its molecular function. Experimental Synthesis Unless otherwise stated, we used the chemicals in their highest available purity. The progress of the synthesis was monitored with MALDI–MS as well as RP-UPLC coupled with ESI–MS. Solid-phase peptide synthesis. The linear

Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline

• Karel Křenek,
• Petr Šimon,
• Lenka Weignerová,
• Barbora Fliedrová,
• Marek Kuzma and
• Vladimír Křen

Beilstein J. Org. Chem. 2012, 8, 428–432, doi:10.3762/bjoc.8.48

• ) decimal places. The anomeric configuration of manno-structures was determined based on the value of 1J (C-1, H-1) [17], which was measured by using gHMQC or gHSQC with retained direct coupling constants between directly bonded carbon and hydrogen. Mass spectrometry Mass spectra were measured on MALDI–TOF

• /TOF ultraFLEX III mass spectrometers (Bruker-Daltonics). Positive spectra were calibrated externally by using the monoisotopic [M + H]+ ions of PepMixII calibrant (Bruker-Daltonics). For the MALDI experiment 0.4 μL of sample dissolved in 50% acetonitrile was allowed to dry at ambient temperature on

• –MALDI–TOF (m/z): 365.1 [M + Na]+ (DHB), 365.1 [M + Na]+ (CCA). p-Nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside (8): Compound 6 (400 mg, 0.85 mmol) was deacetylated and purified as described for compound 7 yielding 8 as a white solid (290 mg, 99%). 1H NMR (400 MHz, CD3OD) δ 2.078 (s, 2-Ac3H

Acceptor-influenced and donor-tuned base-promoted glycosylation

• Stephan Boettcher,
• Martin Matwiejuk and
• Joachim Thiem

Beilstein J. Org. Chem. 2012, 8, 413–420, doi:10.3762/bjoc.8.46

• apparatus. Optical rotations were obtained by using a Krüss Optronic P8000 polarimeter (589 nm, 25 °C). HRMS (ESI) were recorded with a Thermo Finnigan MAT 95XL mass spectrometer. MS (MALDI–TOF) were recorded with a Bruker Biflex II (positive reflection mode, matrix: 2,5-dihydroxybenzoic acid). Relative

• , 127.6, 127.6, 127.5 (Car), 104.2 (C-1’), 97.9 (C-1), 82.3 (C-3’), 79.4 (C-2’), 79.1 (C-2), 79.1 (C-5), 76.3 (C-4’), 75.0, 74.7, 73.2, 73.0 (-O-CH2-Ph), 72.6 (C-3), 70.6 (C-5’), 70.1 (C-4), 68.8 (C-6), 55.2 (-OCH3), 16.7 (C-6’) ppm; MALDI–TOF–MS (DHB, positive mode; m/z): [M + Na]+ calcd for C41H48O10Na

• ), 79.1 (C-2), 75.2, 74.7, 74.5, 73.5, 72.9 (-O-CH2-Ph), 73.5 (C-4), 74.6 (C-5), 74.2 (C-2’), 73.4 (C-4), 71.4 (C-5’), 69.3 (C-6), 68.7 (C-6’), 57.1 (-OCH3) ppm; MALDI–TOF–MS (DHB, positive mode; m/z): [M + Na]+ calcd for C48H54O11Na, 829.36; found, 830.1. Monobenzylated methyl α- and β-D-gluco- and

Synthesis of mesomeric betaine compounds with imidazolium-enolate structure

• Nina Gonsior,
• Fabian Mohr and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 390–397, doi:10.3762/bjoc.8.42

• ). However, the reaction with both monomer balance (a) and imbalance (b) only led to oligomeric compounds (7a,b), which were soluble in water and DMSO but insoluble in, e.g., CHCl3, acetone or toluene. MALDI-TOF mass spectroscopy revealed a maximum repeat unit of m = 3 with 1,4-bis(1H-imidazol-1-yl)butane

• -time-of-flight mass spectrometry (MALDI-TOF-MS) was performed on a Bruker Ultraflex TOF mass spectrometer. Ions formed with a pulsed nitrogen laser (25 Hz, 337 nm) were accelerated to 25 kV, with the molecular masses being recorded in the linear mode. 2,5-Dihydroxybenzoic acid (DBH) in acetonitrile

Binding of group 15 and group 16 oxides by a concave host containing an isophthalamide unit

• Jens Eckelmann,
• Vittorio Saggiomo,
• Svenja Fischmann and
• Ulrich Lüning

Beilstein J. Org. Chem. 2012, 8, 11–17, doi:10.3762/bjoc.8.2

• unit. Elemental analyses were carried out with a EuroEA 3000 Elemental Analyzer from Euro Vector. MALDI-TOF spectra were recorded with Bruker-Daltonics Biflex III. 4-Chloro-α-cyanocinnamic acid (Cl-CCA) was used as the matrix. 1H NMR experiments Each NMR tube was filled with 600 µL of a stock solution

• −1. EIMS (70 eV): m/z (% relative intensity) 656 (100) [M]+•; CIMS (isobutane): m/z (% relative intensity) 657 (30) [M + H]+; ESIMS (CHCl3): m/z (% relative intensity) 679 (100) [M + Na]+, 657 (75) [M + H]+; MS (MALDI-TOF, Cl-CCA): m/z 695 [M + K]+, 679 [M + Na]+, 656 [M]+; HRMS calcd for C40H52N2O6

• (d, 252-C), 116.1 (s, 12,122-C), 105.4 (d, 14,6,124,6-C), 69.5 (t, OCH2), 35.3 (s, C(CH3)3), 31.2 (q, CH3), 30.7 (t, OCH2CH2), 24.9 (t, O(CH2)2CH2); The C=O signal was too weak to be detected in this 13C spectrum. MS (MALDI-TOF, Cl-CCA): m/z 676 [M + Na]+, 654 [M + H]+. Bi-macrocyclic concave host 1

Sexithiophenes as efficient luminescence quenchers of quantum dots

• Christopher R. Mason,
• Yang Li,
• Paul O’Brien,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2011, 7, 1722–1731, doi:10.3762/bjoc.7.202

• ), 7.20 (dd, J = 0.8 and 3.9, 2H), 7.17 (d, J = 3.5, 1H), 7.08 (m, 2H), 6.80 (d, J = 3.7, 1H), 3.36 (s, 8H), 2.86 (t, J = 7.7, 2H), 1.74 (q, 2H), 1.37 (m, 6H), 0.94 (t, J = 6.9, 3H); MS (MALDI-TOF) m/z: 838 (M+, 100%); FTIR (KBr) ν/cm−1: 2924, 2855, 1634, 1266, 1161, 1040; Anal. calcd for C34H29BrS10: C

• , toluene) and then precipitation to afford 7b as a red solid (0.23 g, 20%); mp 195 °C (by DSC); 1H NMR (CDCl3) δ 7.26 (m, 2H), 7.20 (d, J = 4.0, 2H), 7.15 (d, J = 3.5, 1H), 7.08 (m, 2H), 6.80 (d, J = 3.5, 1H), 3.36 (s, 8H), 2.55 (s, 3H); MS (MALDI-TOF) m/z: 769 (M+, 68%), 767 (M+, 100%); FTIR (KBr) ν/cm−1

Highly efficient cyclosarin degradation mediated by a β-cyclodextrin derivative containing an oxime-derived substituent

• Michael Zengerle,
• Florian Brandhuber,
• Christian Schneider,
• Franz Worek,
• Georg Reiter and
• Stefan Kubik

Beilstein J. Org. Chem. 2011, 7, 1543–1554, doi:10.3762/bjoc.7.182

• 600, Bruker DPX 400; MALDI-TOF-MS, Bruker Ultraflex TOF/TOF; ESI–MS, Bruker Esquire 3000; IR, FT-IR System Spectrum BX, Perkin-Elmer; elemental analysis, Elementar vario Micro cube. All chemicals, unless other stated, are commercially available and were used without further purification. Cyclosarin

Stereogenic boron in 2-amino-1,1-diphenylethanol-based boronate–imine and amine complexes

• Sebastian Schlecht,
• Walter Frank and
• Manfred Braun

Beilstein J. Org. Chem. 2011, 7, 615–621, doi:10.3762/bjoc.7.72

• (EI, 70 eV). High resolution mass spectra were carried out on Bruker FT-ICR APEX III (7.0 T) (MALDI) at the University of Bielefeld. Column chromatography was performed with Fluka silica gel 60 (230–400 mesh) and thin layer chromatography was carried out on Merck TLC Silicagel 60 F254 aluminium sheets