Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition

• Nicolas Desbois,
• Sandrine Pacquelet,
• Adrien Dubois,
• Clément Michelin and
• Claude P. Gros

Beilstein J. Org. Chem. 2015, 11, 2202–2208, doi:10.3762/bjoc.11.239

• dissolved in benzonitrile and then refluxed to yield 9d. The target metalated porphyrins 9a–d were isolated in moderate to good yields ranging from 51 to 82% and were fully characterized by 1H NMR, MS (MALDI–TOF) and HRMS (ESI) spectrometry. Alkynyl DOTA/NOTA In a second step, the successful preparation of

Cholesterol lowering effects of mono-lactose-appended β-cyclodextrin in Niemann–Pick type C disease-like HepG2 cells

• Keiichi Motoyama,
• Yumi Hirai,
• Rena Nishiyama,
• Yuki Maeda,
• Taishi Higashi,
• Yoichi Ishitsuka,
• Yuki Kondo,
• Tetsumi Irie,
• Takumi Era and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2015, 11, 2079–2086, doi:10.3762/bjoc.11.224

• , lactose was modified to NH2-β-CyD using the reducing agent cyanotrihydroborate in dimethyl sulfoxide (DMSO) at room temperature for 24 h. No unreacted free lactose was confirmed by thin-layer chromatography (TLC). The MALDI–TOF MS spectrum of Lac-β-CyD showed a peak at m/z 1483 derived from lactose mono

• for protons at 25 °C. The concentration of the sample was 1.5 mg/750 μL in deuterated oxide (D2O), and the chemical shifts were given as parts per million (ppm) downfield from that of tetramethylsilane (TMS). MALDI-TOF mass spectra (MALDI–TOF MS) were measured in a positive mode at 25 °C by a JEOL JMS

• with Scheffe's test. The level of statistical significance was set at p < 0.05. Preparation scheme of Lac-β-CyD. MALDI–TOF MS (A) and 1H NMR (B) spectra of Lac-β-CyD. Cytotoxic activity of β-CyDs in U18666A-treated HepG2 cells after treatment for 24 h. U18666A-treated HepG2 cells were incubated with

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

• Alexander L. Kanibolotsky,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1749–1766, doi:10.3762/bjoc.11.191

• ) revealed by GPC analysis (Table 2) corresponds to about 7 thienoTTF monomer units per polymer chain for 35 and 37, and about 6 units for 39. MALDI–TOF MS characterisation was only successful for polymer 39 and showed a series of peaks with a mass difference of 516 Da, corresponding to the mass of the 2

• -(4,5-bis(hexylthio)-1,3-dithiol-2-ylidene)thieno[3,4-d][1,3]dithiol-4,6-diyl-alt-vinylene repeating unit. The mass spectra confirmed that the polymer was end-capped with a thienoTTF unit, with the terminal bromo substituents still intact. The highest mass peak of 5290 Da registered by MALDI–MS

Robust bifunctional aluminium–salen catalysts for the preparation of cyclic carbonates from carbon dioxide and epoxides

• Yuri A. Rulev,
• Zalina Gugkaeva,
• Victor I. Maleev,
• Michael North and
• Yuri N. Belokon

Beilstein J. Org. Chem. 2015, 11, 1614–1623, doi:10.3762/bjoc.11.176

• cyclic [32] or polycarbonate [33][34] from cyclohexene oxide, depending on the exact structure of the catalyst and cocatalyst. However, this is the first report of a one-component aluminium–salen-based catalyst for polycyclohexene carbonate synthesis. MALDI–TOF mass-spectra data (Figure 2) showed that

• (Figure 3) was consistent with the MALDI–TOF data, showing that most of the polymer has a molecular weight between 300 and 1000 Daltons. This type of low molecular weight polycarbonate–polyol is currently attracting much interest associated with its use in sustainable polyurethanes [35]. To show the

• Spectrometry Service Unit using ESI and MALDI ionization methods. GPC was carried out using a set (PSS SDV High) of 3 analytical columns (300 × 8 mm, particle diameter 5 µm) of 1000, 105 and 106 Å pore sizes, plus guard column, supplied by Polymer Standards Service GmbH (PSS) installed in a PSS SECcurity

Tetrathiafulvalene-based azine ligands for anion and metal cation coordination

• Awatef Ayadi,
• Aziz El Alamy,
• Olivier Alévêque,
• Magali Allain,
• Nabil Zouari,
• Mohammed Bouachrine and
• Abdelkrim El-Ghayoury

Beilstein J. Org. Chem. 2015, 11, 1379–1391, doi:10.3762/bjoc.11.149

• , 107.5 ppm; anal. calcd for C12H7NOS4: C, 46.58; H, 2.28; N, 4.53; found: C, 46.16; H, 2.22; N, 4.43; MALDI–TOF MS calcd: m/z = 309.5. found: m/z = 308.9 [M]+; HRMS (M): calcd for C12H7NOS4: 308.9410; found: 308.9413. 5-([2,2’-Bi(1,3-dithiolylidene)]-4-yl)picolinaldehyde (2): This compound was prepared

• , 131.8, 130.8, 122.6, 122.5, 120.7, 120.6, 114.2, 105.7 ppm; anal. calcd for C12H7NOS4: C, 46.58; H, 2.28; N, 4.53; found: C, 46.54; H, 2.20; N, 4.51; MALDI–TOF MS calcd: m/z = 309.5. found: m/z = 308.9 [M]+. HRMS (M): calcd for C12H7NOS4: 308.9410; found: 308.9404. 2-([2,2’-Bi(1,3-dithiolylidene)]-4-yl

• . calcd for C18H11N5O4S4: C, 44.15; H, 2.26; N, 14.30, found: C, 43.54; H, 2.22; N, 13.66; MALDI–TOF MS calcd: m/z = 489.6. found: m/z = 489.1 [M]+; HRMS (M): calcd for C18H11N5O4S4: 488.9694; found: 488.9687. 5-([2,2’-bi(1,3-dithiolylidene)]-4-yl)-2-((2,4-dinitrophenyl)hydrazono)methyl)pyridine (L2

Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones

• Flavia Pop and
• Narcis Avarvari

Beilstein J. Org. Chem. 2015, 11, 1105–1111, doi:10.3762/bjoc.11.124

• TMS. The following abbreviations are used: d, doublet; t, triplet; m, multiplet. MALDI–TOF MS spectra were recorded on a Bruker Biflex-IIITM apparatus, equipped with a 337 nm N2 laser. Elemental analyses were recorded using Flash 2000 Fisher Scientific Thermo Electron analyzer. The starting compounds

• chromatography using petroleum spirit/dichloromethane 1:1 followed by dichloromethane as eluent, to afford an orange solid (0.53 g, 48%). 1H NMR (300 MHz, CDCl3) δ 3.23–3.17 (m, 2H, -CH-CH3), 3.06 (t, 2H, -CH2-), 2.71 (t, 2H, -CH2-), 1.42 (d, 6H, -CH3) ppm; MALDI–TOF MS (m/z): [M − CH2CH2CN)]+ 437.4; Anal. calcd

• , 116.56, 112.02, 111.44, 50.10, 44.04, 30.38, 27.39, 21.36 ppm; MALDI–TOF MS (m/z): 444 [M]+ (Mcalcd = 443.86); Anal. calcd for C12H12O2S8: C, 32.41; H, 2.72; O, 7.19; S, 57.68; found: C, 32.72; H, 2.55; O, 6.95; S, 57.93 (%). (R,R)-1: The same synthetic procedure was followed as for the (S,S)-enantiomer

Interactions between tetrathiafulvalene units in dimeric structures – the influence of cyclic cores

• Huixin Jiang,
• Virginia Mazzanti,
• Christian R. Parker,
• Søren Lindbæk Broman,
• Jens Heide Wallberg,
• Karol Lušpai,
• Adam Brincko,
• Henrik G. Kjaergaard,
• Anders Kadziola,
• Peter Rapta,
• Ole Hammerich and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2015, 11, 930–948, doi:10.3762/bjoc.11.104

• spectrometry (MS) was performed using Matrix Assisted Laser Desorption Ionization (MALDI); TOF = time-of-flight; FT-ICR = Fourier Transform Ion Cyclotron Resonance. IR spectra were measured using the attenuated total reflectance (ATR) method on diamond. The relative peak intensities in IR spectra are

• ); MS (MALDI–TOF): m/z = 476 [M•+]; HRMS (MALDI+, FT-ICR, dithranol): m/z = 476.02777 [M•+] (calcd for C19H28S6Si+: 476.02790). 1,2-Bis(4,5-bis(butylthio)tetrathiafulvalene)ethyne (4). To a solution of K2CO3 (121 mg, 0.88 mmol) in MeOH (30 mL) was added a solution of 10 (56 mg, 0.12 mmol) in THF (5 mL

• , 2H), 2.83–2.80 (m, 8H), 1.63–1.59 (m, 8H), 1.46–1.41 (m, 8H), 0.93 (t, J = 7.4 Hz, 6H), 0.92 (t, J = 7.4 Hz, 6H) ppm; 13C NMR (126 MHz, CDCl3) δ 128.28, 127.77, 126.50, 114.90, 111.75, 110.43, 84.61, 36.20, 36.19, 31.98, 31.91, 21.95, 13.75 ppm (2 signals missing); MS (MALDI–TOF): m/z = 782 [M

Terminal lipophilization of a unique DNA dodecamer by various nucleolipid headgroups: Their incorporation into artificial lipid bilayers and hydrodynamic properties

• Emma Werz and
• Helmut Rosemeyer

Beilstein J. Org. Chem. 2015, 11, 913–929, doi:10.3762/bjoc.11.103

• the (n−1) position. The integrity of all oligonucleotides was proven by MALDI–TOF mass spectrometry (see Experimental). Insertion of the six LONs into an artificial lipid bilayer and their specific characteristics The different lipo-oligonucleotides (LON 10–15) were incorporated into stable artificial

• purchased from Roth (D-Karlsruhe). All lipo-oligonucleotides 10–15 (Figure 2) were synthesized, purified and characterized by MALDI–TOF mass spectrometry by Eurogentec SA (B-Liege). In each case, the detected mass confirmed the corresponding calculated mass. MALDI–TOF–MS (m/z): 4636.8 (10, [M + H]+; calcd

Orthogonal dual-modification of proteins for the engineering of multivalent protein scaffolds

• Michaela Mühlberg,
• Michael G. Hoesl,
• Christian Kuehne,
• Jens Dernedde,
• Nediljko Budisa and
• Christian P. R. Hackenberger

Beilstein J. Org. Chem. 2015, 11, 784–791, doi:10.3762/bjoc.11.88

• derivative 1 (see Supporting Information File 1), several reaction conditions were screened to achieve full conversion based on MALDI–MS analysis for the Ald-TTL[Aha], in which the unreactive AhaSer-TTL[Aha] served as a reference point (Figure 1A), whereby it has to be noted that due to the limited

• resolution of the MALDI for proteins all detected mass values differ by a few Dalton from the theoretical masses, and the peak intensity for the functionalized biotinylated lipase (Gal-0) was usually lower in all MALDI spectra which was addressed to the lower detectability of Gal-0 due to the attached biotin

• solution [50], was applied in all coupling reactions and conversions were again checked by MALDI–MS, gel electrophoresis and Western Blot (Figure 1B,C, lane 4). As evidenced by MS-analysis, we could observe that both proteins Ser-TTL[Aha] (nine azides) and AhaSer-TTL[Aha] (ten azides) reacted with

Exploring monovalent and multivalent peptides for the inhibition of FBP21-tWW

• Lisa Maria Henning,
• Sumati Bhatia,
• Miriam Bertazzon,
• Michaela Marczynke,
• Oliver Seitz,
• Rudolf Volkmer,
• Rainer Haag and
• Christian Freund

Beilstein J. Org. Chem. 2015, 11, 701–706, doi:10.3762/bjoc.11.80

• according to the published procedure [19] (see Figures S2 and S3 in Supporting Information File 1 for GPC and MALDI–TOF–MS analysis of the hPG-OH core). Seventy percent of all hydroxy groups (≈120 OH groups) on hPG-OH were functionalized with amino groups in a three-step protocol as reported in the

Trifluoromethyl-substituted tetrathiafulvalenes

• Olivier Jeannin,
• Frédéric Barrière and
• Marc Fourmigué

Beilstein J. Org. Chem. 2015, 11, 647–658, doi:10.3762/bjoc.11.73

• des Substances Naturelles (ISCN), Gif/Yvette (France). MALDI-TOF MS spectra were obtained from a Bruker Biflex-IIITM equipped with a 337 nm laser. Syntheses Preparation of EDT-TTF(CONH2)(CF3) (7): EDT-TTF(CO2Me)(CF3) (2bc) [17] (0.2 g, 0.47 mmol) was added to a MeOH solution (20 mL) saturated with

Hetero-Diels–Alder reactions of hetaryl and aryl thioketones with acetylenic dienophiles

• Grzegorz Mlostoń,
• Paulina Grzelak,
• Maciej Mikina,
• Anthony Linden and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2015, 11, 576–582, doi:10.3762/bjoc.11.63

• = triplet, q = quartet, m = multiplet), coupling constant, integration. The mass spectra were recorded on a Finnigan MAT-95 (ESI), Bruker maxis (HRESI), or SYNAPT G2-S HMDS (HR MALDI–TOF) instrument. Elemental analyses were performed in the Microanalytical Laboraory of the Chemistry Faculty in Łódź

• )), 132.2, 130.1, 129.3, 127.8, 127.6, 126.7, 126.7, 126.6, 125.2 (7 CHarom + 2 CHolefin), 53.2, 52.8 (2 OCH3), 41.8 (S-CH) ppm; HRMS (MALDI–TOF): [M + Na]+ calcd for C21H16NaO4S, 387.0668; found, 387.0667. Methyl 11,12-dihydro-4bH-benzo[4,5]cyclohepta[1,2,3-ij]isothiochromene-7-carboxylate (5b): Yield

• + S-CH=), 51.9 (OCH3), 35.0 (S-CH), 32.2 (broad, 2 CH2) ppm; HRMS (MALDI–TOF): [M + Na]+ calcd for C19H16NaO2S, 331.0761; found, 331.0769. Methyl 4bH-benzo[4,5]cyclohepta[1,2,3-ij]isothiochromene-7-carboxylate (5c): Yield: 85 mg (61%). Yellow solid; mp 77.5–78.0 °C (chromatographic purification); IR

Synthesis and surface grafting of a β-cyclodextrin dimer facilitating cooperative inclusion of 2,6-ANS

• Lars W. Städe,
• Thorbjørn T. Nielsen,
• Laurent Duroux,
• Reinhard Wimmer,
• Kyoko Shimizu and
• Kim L. Larsen

Beilstein J. Org. Chem. 2015, 11, 514–523, doi:10.3762/bjoc.11.58

• chemical shifts. The product was further analyzed by MALDI–TOF mass spectrometry for which the dominant contributions in the region of 2400 to 2500 Da (Figure 1) were found. The three peaks observed in this region correspond to the β-CD dimer (2451 Da), sodium (2473 Da) and potassium adducts (2490 Da). In

• . General procedures: MALDI–TOF mass spectrometry was performed on a Reflex III (Bruker Daltonics, Bremen, Germany) and automated flash chromatography was performed on a Grace Davidson Discovery Science Revelaris system. NMR spectra were recorded at 298.1 K on a Bruker AVIII-600 MHz instrument equipped with

Sequence-specific RNA cleavage by PNA conjugates of the metal-free artificial ribonuclease tris(2-aminobenzimidazole)

• Friederike Danneberg,
• Alice Ghidini,
• Plamena Dogandzhiyski,
• Elisabeth Kalden,
• Roger Strömberg and
• Michael W. Göbel

Beilstein J. Org. Chem. 2015, 11, 493–498, doi:10.3762/bjoc.11.55

• , DIC and HOBt were used as reagents. Coupling of the cleaver proceeded in high yields with no unconjugated PNA detectable in the MALDI mass spectra of the crude products. All conjugates were purified by RP-HPLC and isolated as trifluoroacetate salts. Starting from 20–30 mg of Rink amide MBHA resin

Functionalized branched EDOT-terthiophene copolymer films by electropolymerization and post-polymerization “click”-reactions

• Miriam Goll,
• Adrian Ruff,
• Erna Muks,
• Felix Goerigk,
• Beatrice Omiecienski,
• Ines Ruff,
• Rafael C. González-Cano,
• Juan T. Lopez Navarrete,
• M. Carmen Ruiz Delgado and
• Sabine Ludwigs

Beilstein J. Org. Chem. 2015, 11, 335–347, doi:10.3762/bjoc.11.39

• NMR and MALDI–TOF spectroscopy indicated that the EDOT and 3T units are covalently linked. While comparisons with these chemically synthesized polymers support our finding, a real proof of copolymer formation for the electropolymerized films was still missing in our previous publication. Here, we show

TEMPO-derived spin labels linked to the nucleobases adenine and cytosine for probing local structural perturbations in DNA by EPR spectroscopy

• Dnyaneshwar B. Gophane and
• Snorri Th. Sigurdsson

Beilstein J. Org. Chem. 2015, 11, 219–227, doi:10.3762/bjoc.11.24

• gel electrophoresis. The incorporation of TA, UA and UC into DNA was confirmed by MALDI–TOF mass spectrometry (Table S1, Supporting Information File 1). Circular dichroism measurements showed that the incorporation of TA, UA and UC does not alter the B-DNA conformation of DNA duplexes containing these

Synthesis and biological evaluation of a novel MUC1 glycopeptide conjugate vaccine candidate comprising a 4’-deoxy-4’-fluoro-Thomsen–Friedenreich epitope

• Manuel Johannes,
• Maximilian Reindl,
• Bastian Gerlitzki,
• Edgar Schmitt and
• Anja Hoffmann-Röder

Beilstein J. Org. Chem. 2015, 11, 155–161, doi:10.3762/bjoc.11.15

• toxoid (TTox) as carrier proteins in aqueous phosphate buffer at pH 9.5. Both 4’F-6TF-MUC1(20)-protein conjugates 18a/b were obtained after ultrafiltration using a 30 kDa membrane. MALDI–TOF mass spectrometry proved the antigen loading level of 18a to be on average seven molecules of glycopeptide per

Redox active dendronized polystyrenes equipped with peripheral triarylamines

• Toshiki Nokami,
• Naoki Musya,
• Tatsuya Morofuji,
• Keiji Takeda,
• Masahiro Takumi,
• Akihiro Shimizu and
• Jun-ichi Yoshida

Beilstein J. Org. Chem. 2014, 10, 3097–3103, doi:10.3762/bjoc.10.326

• dendronized polystyrene 8a was characterized using MALDI–TOF MS analysis. Six peak groups were observed, as shown in Figure 4. The peak occurring at 10,573 Da [M + Ag+] is derived from 11 dendritic substituents (815 Da × 11), 14 styrene units (103 Da × 11 + 104 Da × 3), and a butyl group (58 Da), which was

• ). Preparation of dendronized polystyrenes having peripheral diarylamino groups. MALDI–TOF MS analysis of the dendronized polystyrene with peripheral bromo groups. Cyclic voltammograms of dendronized polystyrene 9 (black line), model compound 10 (blue line), and the film of dendronized polystyrene 9 (red line

Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin

• Jun Terao,
• Yohei Konoshima,
• Akitoshi Matono,
• Hiroshi Masai,
• Tetsuaki Fujihara and
• Yasushi Tsuji

Beilstein J. Org. Chem. 2014, 10, 2800–2808, doi:10.3762/bjoc.10.297

• /H2O 5:1) instead of hydrophilic solvent (CH3OH/H2O 1:1). Although the MALDI–TOF mass spectrum of 8 and 9 exhibited the same signal at m/z = 6097 corresponding to [8 or 9 + Na]+, each 1H NMR spectrum of those showed the pure single product but completely different, respectively. These results suggest

Synthesis and properties of novel star-shaped oligofluorene conjugated systems with BODIPY cores

• Clara Orofino-Pena,
• Diego Cortizo-Lacalle,
• Joseph Cameron,
• Muhammad T. Sajjad,
• Pavlos P. Manousiadis,
• Neil J. Findlay,
• Alexander L. Kanibolotsky,
• Dimali Amarasinghe,
• Peter J. Skabara,
• Tell Tuttle,
• Graham A. Turnbull and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2704–2714, doi:10.3762/bjoc.10.285

• (in ppm) in which they appear. MS MALDI–TOF spectra were recorded on a Shimadzu Axima-CFR spectrometer (mass range 1–150,000 Da). Retinoic acid was used as a matrix. Elemental analyses were obtained on a PERKIN ELMER 2400 elemental analyser. Commercial TLC plates (Silica gel 60 F254) were used for TLC

Solution processable diketopyrrolopyrrole (DPP) cored small molecules with BODIPY end groups as novel donors for organic solar cells

• Diego Cortizo-Lacalle,
• Calvyn T. Howells,
• Upendra K. Pandey,
• Joseph Cameron,
• Neil J. Findlay,
• Anto Regis Inigo,
• Tell Tuttle,
• Peter J. Skabara and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2683–2695, doi:10.3762/bjoc.10.283

• through a PureSolv purification system. 1H and 13C NMR spectra were recorded at room temperature on a Bruker DRX500 at 500 and 125 MHz or a Bruker Avance 400 instrument at 400 and 100 MHz; chemical shifts are given in ppm and all J values are in Hz. MALDI–TOF–MS were recorded on a Shimadzu Axima-CFR

• , 131.0, 130.1, 128.7, 128.1, 124.7, 124.6, 108.2, 45.8, 37.5, 31.4, 31.3, 30.8, 29.5, 29.1, 29.09, 29.04, 28.8, 28.7, 25.8, 22.1, 16.6, 14.0, 13.5, 12.1, 10.8; MALDI–MS m/z: 1628.3 [M+]; Anal. calcd for C96H134B2F4N6O2S4: C, 70.74; H, 8.29; N, 5.16; S, 7.87; found: C, 68.78; H, 8.05; N, 5.56; S, 8.09; MP

• , 138.8, 138.1, 138.0, 136.7, 136.1, 134.9, 134.7, 132.8, 131.1, 130.4, 128.5, 127.9, 125.3, 124.6, 124.4, 123.6, 108.1, 45.8, 37.4, 31.4, 30.8, 29.5, 29.1, 29.0, 28.9, 28.8, 25.9, 22.1, 16.6, 14.0, 13.6, 12.1, 10.8; MALDI–MS m/z: 1794.2 [M+]; Anal. calcd for C104H138B2F4N6O2S6: C, 69.62; H, 7.75; N, 4.68

Towards the sequence-specific multivalent molecular recognition of cyclodextrin oligomers

• Michael Kurlemann and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2014, 10, 2428–2440, doi:10.3762/bjoc.10.253

• functionalized α- and β-CD, again followed by complete deprotection under Zemplén conditions (Figure 2). Based on MALDI mass spectra of the protected and unprotected cyclodextrin strands impurities by monomeric building blocks respectively dimeric species in the case of trivalent strands can be excluded (see

A versatile δ-aminolevulinic acid (ΑLA)-cyclodextrin bimodal conjugate-prodrug for PDT applications with the help of intracellular chemistry

• Chrysie Aggelidou,
• Theodossis A. Theodossiou,
• Antonio Ricardo Gonçalves,
• Mariza Lampropoulou and
• Konstantina Yannakopoulou

Beilstein J. Org. Chem. 2014, 10, 2414–2420, doi:10.3762/bjoc.10.251

• the HSQC-edited spectrum (Supporting Information File 1, Figure S3). The ratio 8 to 4 was ~3, as indicated by integration of the respective signals and also confirmed by MALDI–TOF MS measurements (m/z 1853, Supporting Information File 1, Figure S4), whereas the IR spectrum exhibited the characteristic

• -dicycloxylurea byproduct) ppm; IR ν: 2104.2 (vs) cm−1; MS (MALDI–TOF) m/z: 1853.7 (100%, [M + Η]+); Exact mass calculated for C71H120N16O41 (9): 1852.78. Ester of δ-aminolevulinic acid with heptakis(6-hydroxyethylamino-6-deoxy)-β-cyclodextrin (2). To a solution of 9 (20 mg, 0.0112 mmol) in ethanol (1 mL

• ΄), 34.4 (C3), 27.1 (C2) ppm; MS (MALDI–TOF) m/z: 1685.2 (100%, [M + Νa]+), 1798.18 (89%, [M’ + Na]+); exact mass calculated for C66H119N9O39 ((1)2-CD = M): 1661.76 and for C71H126N10O41 ((1)3-CD = M’): 1774.808. Complexation of fluorescein isothiocyanate-labeled 1-adamantylamine with 2. The conjugate, 2

Phosphinocyclodextrins as confining units for catalytic metal centres. Applications to carbon–carbon bond forming reactions

• Matthieu Jouffroy,
• Rafael Gramage-Doria,
• David Sémeril,
• Dominique Armspach,
• Dominique Matt,
• Werner Oberhauser and
• Loïc Toupet

Beilstein J. Org. Chem. 2014, 10, 2388–2405, doi:10.3762/bjoc.10.249

• shifts are reported relative to deuterated solvents (δ = 77.16 ppm for CDCl3) and the 31P NMR data are given relative to external H3PO4. Mass spectra were recorded either on a Maldi TOF spectrometer (MALDI–TOF) using α-cyano-4-hydroxycinnamic acid as matrix, or on a Bruker MicroTOF spectrometer (ESI–TOF

• – CO + Cl]−; MS (MALDI–TOF): m/z (%): 1605.58 (100) [M – CO – Cl]+, 1719.69 (5) [M + CO + Na]+. 11: A solution of [Rh(CO)2Cl]2 (0.080 g, 0.20 mmol) in CH2Cl2 (7 mL) was added dropwise to a solution of HUGPHOS-2 (0.100 g, 0.07 mmol) in CH2Cl2 (5 mL) under vigorous stirring at room temperature. After 1 h

Synthesis and immunological evaluation of protein conjugates of Neisseria meningitidis X capsular polysaccharide fragments

• Laura Morelli,
• Damiano Cancogni,
• Marta Tontini,
• Alberto Nilo,
• Sara Filippini,
• Paolo Costantino,
• Maria Rosaria Romano,
• Francesco Berti,
• Roberto Adamo and
• Luigi Lay

Beilstein J. Org. Chem. 2014, 10, 2367–2376, doi:10.3762/bjoc.10.247

• excess of unconjugated carbohydrate by precipitation with ammonium sulfate and reconstitution in 10 mM NaPi pH 7.2. The occurrence of conjugation was assessed by SDS-PAGE (sodium dodecyl sulfate polyacrylamide gel electrophoresis) and MALDI–TOF mass spectrometry (see Supporting Information File 1). The

• subsequently reconstituted with 10 mM NaPi pH 7. Yields (recovered glycoprotein as determined by microBCA, Pierce Thermo): 85–95%. Loading of glycoconjugate was determined by matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI–TOF MS; UltraFlex III MALDI–TOF/TOF instrument

• gratefully acknowledge MIUR-Italy (PRIN 2010-2011: contract 2010JMAZML_003) for financial support. We are grateful to Stefano Crotti for contributing to the MALDI TOF analysis of glycoconjugates.