Synthesis and characterization of a first generation organorhenium dendrimer

Mavunkal, Ipe J.; Moss, John R.; Bacsa, John

doi:10.1016/s0022-328x(99)00543-4

Cited by 15 publications

(14 citation statements)

References 16 publications

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“…For the ReL3- and ReL4-labels, the route to the iodide is direct from the lithium-activated Cp-ring with diiodopropane or diiodobutane to [η 5 -(C 5 H 4 )(CH 2 ) 3 I]Re(CO) 3 ( 5 ) or [η 5 -(C 5 H 4 )(CH 2 ) 4 I]Re(CO) 3 ( 4 ), respectively. 44 For all iodide products, [η 5 -(C 5 H 4 )(CH 2 ) n I]Re(CO) 3 where n=1,3 or 4, the iodide is replaced using NaSSO 2 CH 3 in DMF to give [η 5 -(C 5 H 4 )(CH 2 ) n SSO 2 CH 3 ]Re(CO) 3 where n=1,3 or 4 ( 1a–c ). The product was purified and DMF removed by diluting in water and extracting into ethyl acetate, which was subsequently washed with water and dried to give CpLx.…”

Section: Methodsmentioning

confidence: 99%

A Strongly Absorbing Class of Non-Natural Labels for Probing Protein Electrostatics and Solvation with FTIR and 2D IR Spectroscopies

et al. 2013

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A series of non-natural infrared probes is reported that consist of a metal-tricarbonyl modified with a -(CH2)n- linker and cysteine-specific leaving group. They can be site-specifically attached to proteins using mutagenesis and similar protocols for EPR spin labels, which have the same leaving group. We characterize the label’s frequencies and lifetimes using 2D IR spectroscopy in solvents of varying dielectric. The frequency range spans 10 cm−1, and the variation in lifetimes ranges from 6 to 19 ps, indicating that these probes are very sensitive to their environments. Also, we attached probes with -(CH2)-, -(CH2)3-, -(CH2)4- linkers to ubiquitin at positions 6 and 63 and collected spectra in aqueous buffer. The frequencies and lifetimes were correlated for 3C and 4C linkers, as they were in the solvents, but did not correlate for the 1C linker. We concluded that lifetime measures solvation, whereas frequency reflects the electrostatics of the environment, which in the case of the 1C linker is a measure of the protein electrostatic field. We also labeled V71C α-synuclein in buffer and membrane-bound. Unlike most other infrared labels, this label has extremely-strong cross-sections and so can be measured with 2D IR spectroscopy at sub-millimolar concentrations. We expect that these labels will find use in studying the structure and dynamics of membrane-bound, aggregated, and kinetically-evolving proteins for which high signal-to-noise at low protein concentrations is imperative.

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Section: Methodsmentioning

confidence: 99%

A Strongly Absorbing Class of Non-Natural Labels for Probing Protein Electrostatics and Solvation with FTIR and 2D IR Spectroscopies

et al. 2013

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“…Moss and coworkers [61] have recently reported the synthesis of a first generation organorhenium dendrimer 38 containing six CpRe(CO) 3 units in the periphery. Using methodology previously employed to assemble Fe and Ru dendrimers [5,6,20], the synthesis consists of the assembly of Fréchet-type wedges containing two rhenium centers and coupling them, through a benzylic bromide, to the 1,1,1-tris(4-hydroxyphenyl)ethane core.…”

Section: Dendrimers Containing Non-ferrocene Organometallic Groups Inmentioning

confidence: 99%

Where Organometallics and Dendrimers Merge: The Incorporation of Organometallic Species into Dendritic Molecules

2005

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This review will describe the ongoing efforts being made to incorporate organometallic fragments into the framework of dendrimers. While purely dendritic organic molecules are well known and well studied, species incorporating organometallic moieties potentially offer many benefits that are not available to only organic containing dendrimers. For example, catalytic or redox active organometallic functions can be included in the dendritic framework and impart these characteristics onto the dendrimer. This report will give an overview of the latest developments in this field by highlighting selected examples that detail novel synthetic strategies or dendrimer construction methodologies, interesting practical applications or address specific problems associated with organometallic dendrimers.

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“…Since we performed this reaction using the normal reaction conditions, and negligible nucleophilic substitution occurred, we did not investigate the reaction further. We also previously reported on the synthesis of CpRe(CO) 3 functionalised benzylphenyl ether dendrimers [12] and decided to investigate the reaction of K[CpRe(CO) 3 ] with dendrimer 1 but unfortunately the reaction of dendrimer 1 with K[CpRe(CO) 3 ] was also proved unsuccessful. Reaction of dendrimer 1 with tetramethylcyclopentadienyllithium or -sodium in refluxing THF did not give the expected tetramethylcyclopentadiene terminated dendrimer, nor did reaction of 1 with eight equivalents of tert-BuLi in diethyl ether at )78°C result in the lithiated dendrimer [13].…”

Section: Resultsmentioning

confidence: 99%

“…Tetraallylsilane and allyltrimethylsilane were purchased from Sigma Aldrich. [CpFe(CO) 2 ] 2 and Ru 3 (CO) 12 were purchased from Strem. (Chloromethyl)dimethylsilane [16], Si[(CH 2 ) 3 SiMe 2 CH 2 Cl] 4 [8] and [CpRu(CO) 2 ] 2 [17] were prepared by literature methods.…”

Section: General Remarksmentioning

confidence: 99%