Synthesis and characterization of ruthenium and rhenium nucleosides

Peijiao Wang; Jeremiah E. Miller; Lawrence M. Henling; Charlotte L. Stern; Natia L. Frank; Amanda L. Eckermann; Thomas J. Meade

doi:10.1021/ic701250r

Synthesis and characterization of ruthenium and rhenium nucleosides

Peijiao Wang, Jeremiah E. Miller, Lawrence M. Henling, Charlotte L. Stern, Natia L. Frank, Amanda L. Eckermann, Thomas J. Meade^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

We report the synthesis and characterization of new ruthenium and rhenium nucleosides [Ru(tolyl-acac)₂(IMPy)-T] (tolyl-acac = di(p-methylbenzonatemethane), IMPy = 2′-iminomethylpyridine, T = thymidine) (5) and [Re(CO)₃-(IMPy)-T]Cl (9), respectively. Structural analysis of 9 shows that the incorporation of this metal complex causes minimal perturbation to the sugar backbone and the nucleobase. Eletrochemical (5, E_1/2 = 0.265 V vs NHE; 9, E_1/2 = 1.67 V vs NHE), absorption (5, λ_max = 600, 486 nm; 9, λ_max = 388 nm), and emission (9, λ_max = 770 nm, π = 17 ns) data indicate that 5 and 9 are suitable probes for DNA-mediated ground-state electron-transfer studies. The separation and characterization of diastereoisomers of 5 and bipyridyl-based ruthenium nucleoside [Ru(bpy) ₂-(IMPy)-T]²⁺ (7) are reported.

Original language	English (US)
Pages (from-to)	9853-9862
Number of pages	10
Journal	Inorganic chemistry
Volume	46
Issue number	23
DOIs	https://doi.org/10.1021/ic701250r
State	Published - Nov 12 2007

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ASJC Scopus subject areas

Inorganic Chemistry
Physical and Theoretical Chemistry

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10.1021/ic701250r

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@article{3f2f5bd2b63545c48e4bc7203a749870,

title = "Synthesis and characterization of ruthenium and rhenium nucleosides",

abstract = "We report the synthesis and characterization of new ruthenium and rhenium nucleosides [Ru(tolyl-acac)2(IMPy)-T] (tolyl-acac = di(p-methylbenzonatemethane), IMPy = 2′-iminomethylpyridine, T = thymidine) (5) and [Re(CO)3-(IMPy)-T]Cl (9), respectively. Structural analysis of 9 shows that the incorporation of this metal complex causes minimal perturbation to the sugar backbone and the nucleobase. Eletrochemical (5, E1/2 = 0.265 V vs NHE; 9, E1/2 = 1.67 V vs NHE), absorption (5, λmax = 600, 486 nm; 9, λmax = 388 nm), and emission (9, λmax = 770 nm, π = 17 ns) data indicate that 5 and 9 are suitable probes for DNA-mediated ground-state electron-transfer studies. The separation and characterization of diastereoisomers of 5 and bipyridyl-based ruthenium nucleoside [Ru(bpy) 2-(IMPy)-T]2+ (7) are reported.",

author = "Peijiao Wang and Miller, {Jeremiah E.} and Henling, {Lawrence M.} and Stern, {Charlotte L.} and Frank, {Natia L.} and Eckermann, {Amanda L.} and Meade, {Thomas J.}",

year = "2007",

month = nov,

day = "12",

doi = "10.1021/ic701250r",

language = "English (US)",

volume = "46",

pages = "9853--9862",

journal = "Inorganic chemistry",

issn = "0020-1669",

publisher = "American Chemical Society",

number = "23",

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T1 - Synthesis and characterization of ruthenium and rhenium nucleosides

AU - Wang, Peijiao

AU - Miller, Jeremiah E.

AU - Henling, Lawrence M.

AU - Stern, Charlotte L.

AU - Frank, Natia L.

AU - Eckermann, Amanda L.

AU - Meade, Thomas J.

PY - 2007/11/12

Y1 - 2007/11/12

N2 - We report the synthesis and characterization of new ruthenium and rhenium nucleosides [Ru(tolyl-acac)2(IMPy)-T] (tolyl-acac = di(p-methylbenzonatemethane), IMPy = 2′-iminomethylpyridine, T = thymidine) (5) and [Re(CO)3-(IMPy)-T]Cl (9), respectively. Structural analysis of 9 shows that the incorporation of this metal complex causes minimal perturbation to the sugar backbone and the nucleobase. Eletrochemical (5, E1/2 = 0.265 V vs NHE; 9, E1/2 = 1.67 V vs NHE), absorption (5, λmax = 600, 486 nm; 9, λmax = 388 nm), and emission (9, λmax = 770 nm, π = 17 ns) data indicate that 5 and 9 are suitable probes for DNA-mediated ground-state electron-transfer studies. The separation and characterization of diastereoisomers of 5 and bipyridyl-based ruthenium nucleoside [Ru(bpy) 2-(IMPy)-T]2+ (7) are reported.

AB - We report the synthesis and characterization of new ruthenium and rhenium nucleosides [Ru(tolyl-acac)2(IMPy)-T] (tolyl-acac = di(p-methylbenzonatemethane), IMPy = 2′-iminomethylpyridine, T = thymidine) (5) and [Re(CO)3-(IMPy)-T]Cl (9), respectively. Structural analysis of 9 shows that the incorporation of this metal complex causes minimal perturbation to the sugar backbone and the nucleobase. Eletrochemical (5, E1/2 = 0.265 V vs NHE; 9, E1/2 = 1.67 V vs NHE), absorption (5, λmax = 600, 486 nm; 9, λmax = 388 nm), and emission (9, λmax = 770 nm, π = 17 ns) data indicate that 5 and 9 are suitable probes for DNA-mediated ground-state electron-transfer studies. The separation and characterization of diastereoisomers of 5 and bipyridyl-based ruthenium nucleoside [Ru(bpy) 2-(IMPy)-T]2+ (7) are reported.

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JO - Inorganic chemistry

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Synthesis and characterization of ruthenium and rhenium nucleosides

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CCDC 658537: Experimental Crystal Structure Determination

CCDC 658536: Experimental Crystal Structure Determination

CCDC 658538: Experimental Crystal Structure Determination

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Synthesis and characterization of ruthenium and rhenium nucleosides

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CCDC 658537: Experimental Crystal Structure Determination

CCDC 658536: Experimental Crystal Structure Determination

CCDC 658538: Experimental Crystal Structure Determination

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