Proton, sodium-23, and phosphorus-31 NMR studies of the self-assembly of the 5'-guanosine monophosphate dianion in neutral aqueous solution in the presence of sodium cations

Borzo, Marie; Detellier, Christian; Laszlo, Pierre; Paris, Agnès

doi:10.1021/ja00523a032

Cited by 103 publications

(72 citation statements)

References 6 publications

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“…Multinuclear NMR studies by Laszlo, Detellier, and co-workers were especially insightful. [47,69,70] Analysis by 23 Na NMR spectroscopy revealed that the Na + ions moved in and out of the [3] 8 ·Na + octamer 10 4 -10 8 times per second, which is orders of magnitude faster than ligand exchange. [69] These assemblies did not need to fully dissociate to release their guests, which suggests that such systems might be useful for mediating cation exchange.…”

Section: ·4 Picmentioning

confidence: 98%

“…Discrete cation-bound octamers of the type G 8 ·M + were proposed to be the building blocks for extended columns of stacked G-quartets (Figure 7). Despite different conclusions about stoichiometry and stereochemistry, [46,47] it was clear that G-quartets were the foundation for the self-assembly of guanosine. The basics of guanosine self-assembly were confirmed by dynamic light scattering, single-crystal X-ray, electrospray mass spectrometric, and solid-state NMR spectroscopic studies.…”

Section: ·4 Picmentioning

confidence: 99%

“…Cation binding plays an important role, together with and reinforcing the hydrogen bonding of the guanines into planar tetramers." [47] Finally, one active area in supramolecular chemistry involves the self-organization of noncovalent assemblies, which is important in materials science and nanoscience. [71] The G-quartet system based on 5'-GMP (3) provides a nice example of this self-assembly/self-organization paradigm.…”

Section: ·4 Picmentioning

confidence: 99%

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G‐Quartets 40 Years Later: From 5′‐GMP to Molecular Biology and Supramolecular Chemistry

Davis¹

2004

Angew Chem Int Ed

1,545

525

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Molecular self-assembly is central to many processes in both biology and supramolecular chemistry. The G-quartet, a hydrogen-bonded macrocycle formed by cation-templated assembly of guanosine, was first identified in 1962 as the basis for the aggregation of 5'-guanosine monophosphate. We now know that many nucleosides, oligonucleotides, and synthetic derivatives form a rich array of functional G-quartets. The G-quartet surfaces in areas ranging from structural biology and medicinal chemistry to supramolecular chemistry and nanotechnology. This Review integrates and summarizes knowledge gained from these different areas, with emphasis on G-quartet structure, function, and molecular recognition.

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Section: ·4 Picmentioning

confidence: 98%

Section: ·4 Picmentioning

confidence: 99%

Section: ·4 Picmentioning

confidence: 99%

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G‐Quartets 40 Years Later: From 5′‐GMP to Molecular Biology and Supramolecular Chemistry

Davis¹

2004

Angew Chem Int Ed

1,545

525

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“…Es wurde vermutet, dass diskrete, kationgebundene Octamere vom Typ G 8 ·M + als Bausteine für längere Säulen aus gestapelten G-Quartetts dienen (Abbildung 7). Trotz abweichender Schlussfolgerungen bezüglich der Stö-chiometrie und der Konfiguration [46,47] stand fest, dass die Selbstorganisation von Guanosin auf G-Quartetts beruht. Durch dynamische Lichtstreuung, Einkristallstrukturanalyse, Elektrospray-Massenspektrometrie und Festkörper-NMRSpektroskopie wurden die Grundzüge der Selbstorganisation von Guanosin bestätigt.…”

Section: ·4 Picunclassified

40 Jahre G‐Quartetts: von 5′‐GMP zur Molekularbiologie und Supramolekularen Chemie

Davis

2004

Angewandte Chemie

234

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Die molekulare Selbstorganisation spielt bei vielen Prozessen in der Biologie und der Supramolekularen Chemie eine zentrale Rolle. Das G‐Quartett, ein durch Selbstorganisation von Guanosin an einem kationischen Templat gebildeter, wasserstoffverbrückter Makrocyclus, wurde erstmals 1962 als Basiseinheit der Aggregation von 5′‐Guanosinmonophosphat nachgewiesen. Inzwischen weiß man, dass viele Nucleoside, Oligonucleotide und synthetische Derivate eine Vielzahl funktionaler G‐Quartetts bilden. Das G‐Quartett spielt in vielen Bereichen eine Rolle, angefangen von der Strukturbiologie und der Medizinischen Chemie bis zur Supramolekularen Chemie und Nanotechnologie. Dieser Aufsatz fasst die Ergebnisse aus den unterschiedlichen Gebieten zusammen, wobei der Schwerpunkt auf der Struktur, der Funktion und der molekularen Erkennung des G‐Quartetts liegt.

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“…Such Gquartet pairing alignments have been observed and characterized in systems ranging from guanine monophosphates (Pinnavaia, Miles & Becker, 1975;Pinnavaia et al, 1978;Borzo, Detellier, Lazlo & Paris, 1980) to , (~ 1996 International Union of Crystallography Printed in Great Britain -all rights reserved polyguanylic acid (Gellert, Lipsett & Davies, 1962). More recent interest has been in the direction of higher order structures adopted by single-stranded telomeric overhangs at the ends of chromosomes (Blackburn & Szostak, 1984;Blackburn, 1991).…”

Section: Introductionmentioning

confidence: 99%

An Ambiguous Structure of a DNA 15-mer Thrombin Complex

Padmanabhan

Tulinsky²

1996

Acta Crystallogr D Biol Crystallogr

168

194

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The structure of a complex between thrombin and a GGTTGGTGTGGTTGG DNA 15-mer has been analyzed crystallographically. The solution NMR structure of the 15-mer has two stacked G-quartets similar to that found in the previous X-ray structure determination of the 15-mer-thrombin complex [Padmanabhan, Padmanabhan, Ferrara, Sadler & Tulinsky (1993). J. Biol. Chem. 268, 17651-17654]; the strand polarity, however, is reversed from that of the crystallographic structure. The structure of the complex here has been redetermined with better diffraction data confirming the previous crystallographic structure but also indicating that the NMR solution structure fits equally well. Both 15-mer complex structures refined to an R value of about 0.16 presenting a disconcerting ambiguity. Since the two 15-mer structures associate with thrombin in different ways (through the TGT loop in the X-ray and TT loop in the NMR model), other independent lines of physical or chemical evidence are required to resolve the ambiguity.

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Proton, sodium-23, and phosphorus-31 NMR studies of the self-assembly of the 5'-guanosine monophosphate dianion in neutral aqueous solution in the presence of sodium cations

Cited by 103 publications

References 6 publications

G‐Quartets 40 Years Later: From 5′‐GMP to Molecular Biology and Supramolecular Chemistry

G‐Quartets 40 Years Later: From 5′‐GMP to Molecular Biology and Supramolecular Chemistry

40 Jahre G‐Quartetts: von 5′‐GMP zur Molekularbiologie und Supramolekularen Chemie

An Ambiguous Structure of a DNA 15-mer Thrombin Complex

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