75956-64-8Relevant academic research and scientific papers
Chiral amide directed assembly of a diastereo- and enantiopure supramolecular host and its application to enantioselective catalysis of neutral substrates
Zhao, Chen,Sun, Qing-Fu,Hart-Cooper, William M.,Dipasquale, Antonio G.,Toste, F. Dean,Bergman, Robert G.,Raymond, Kenneth N.
supporting information, p. 18802 - 18805 (2014/01/06)
The synthesis of a novel supramolecular tetrahedral assembly of K 12Ga4L6 stoichiometry is reported. The newly designed chiral ligand exhibits high diastereoselective control during cluster formation, leading exclusively t
Gallium(III) catecholate complexes as probes for the kinetics and mechanism of inversion and isomerization of siderophore complexes
Kersting, Berthold,Telford, Jason R.,Meyer, Michel,Raymond, Kenneth N.
, p. 5712 - 5721 (2007/10/03)
The catechol siderophore analog K3[Ga(3)3], 4 (H23 = 2,3-dihydroxy-N,N'-diisopropylterephthalamide), is D3-symmetric in aqueous solution, and exists in two enantiomeric forms, Δ-4 and Λ-4. Variable temperature N
Potentiometric, spectrophotometric, and 1H NMR study of four desferrioxamine B derivatives and their ferric complexes
Hou, Zhiguo,Whisenhunt Jr., Donald W.,Xu, Jide,Raymond, Kenneth N.
, p. 840 - 846 (2007/10/02)
A new octadentate terephthalamide desferrioxamine B (DFO) derivative, N-(2,3-dihydroxy-4-(methylamido)-benzoyl)desferrioxamine B (DFOMTA), has been prepared. This ligand and three other DFO derivatives [N-(2,3-dihydroxybenzoyl)desferrioxamine B (DFOCAM),
Azaparacyclophanes with Metal-binding Sites. Part 1. Preparation, Characterization, and Molecular Recognition Behaviour of Hexapus Azaparacyclophane and its Iron(III) Complex
Hisaeda, Yoshio,Ihara, Takeshi,Ohno, Teruhisa,Murakami, Yukito,Maeda, Yonezo
, p. 595 - 604 (2007/10/02)
All the catechol moieties of a hexapus triazaparacyclophane having three catechol moieties and six hydrocarbon chains (1) undergo coordination interactions with the iron(III) ion in a 1:1 molar ratio of 1 to iron(III) above pH 6 in an aqueous medium.Two different iron(III) complexes of 1, A and B in a 1:1 molar ratio, are in the high spin iron(III) state as characterized by electronic, EPR and Moessbauer spectroscopy: A is a hexacoordinated mononulear complex with half-protonated catecholato groups, subjected to considerable structural distortion; B is ahexacoordinated mononuclear complex with complete dissociation of all the catechol protons, retaining high structural symmetry.The molecular recognition behaviour of 1 and Fe-complex A toward hydrophobic guest molecules has been investigated in aqueous HEPES and acetate buffers at 30.0 deg C and μ 0.10 mol dm-3.The hexapus cyclophane 1 recognizes organic guests through hydrophobic and electrostatic interactions; anionic and non-ionic quests, 7-hydroxy-8-phenylazonaphthalene-1,3-disulfonate (OG) and 2-hydroxy-1-(2-pyridylazo)naphthalene (PAN), respectively, are incorporated into host 1 with binding constants of the order of 105 dm3 mol-1, while a cationic guest, 2-(p-dimethylaminostyryl)-1-ethylquinolinium (QR), is not included in the host.The guest-binding behaviour of Fe-complex A toward OG and PAN is much enhanced relative to that of 1 as effected by hydrophobic, electrostatic and coordination interactions under conditions identical to those applied to 1; the binding constant for OG is nearly pH-independent in a pH range of 3-8, while that for PAN is pH-dependent because the coordination interaction with the host is subject to change by pH.
Large Oligocyclic Cavities for Strong Cation Complexation
Kiggen, W.,Voegtle, F.,Franken, S.,Puff, H.
, p. 1859 - 1872 (2007/10/02)
The syntheses of oligocyclic large cavities containing two or three catechol subunits are described.The X-ray analysis of a heptacyclic molecule composed of three triply clamped dimethyl catechol ether units demonstrates the size and shape of the cavity formed by this skeleton.Properties of the Fe(3+)- and Ga(3+)-complexes are elucidated by (1)H-NMR, IR, UV/Vis spectra, and by competition experiments with an open-chained reference ligand.
Synthetic Enterobactin Analogues. Carboxamido-2,3-dihydroxyterephthalate Conjugates of Spermine and Spermidine
Weitl, Frederick L.,Raymond, Kenneth N.,Durbin, Patricia W.
, p. 203 - 206 (2007/10/02)
Two examples of a new class of synthetic polycatecholate ligands, the carboxamido-2,3-dihydroxyterephthalate conjugates of spermine (8) and spermidine (10), have been synthesized via the generally useful synthon methyl-2,3-dimethoxyterephthaloyl chloride (6).Initial biological evaluation reveals tetrameric terephthalate (8) to be an extremely effective agent for sequestering and removing plutonium from mice; a single 25-μmol/kg (ip) dose of 8 removed 73percent of the plutonium citrate previously injected (iv,1h earlier).Under the same conditions, trimeric terephthalate (10) ex creted only 49percent injected plutonium.In vitro kinetic experiments have shown that 10 rapidly and quantitatively removed Fe from human transferrin.These results are discussed in relation to the design of metal-ion specific sequestering agents.
