Multistep Electron Transfer in Oligopeptides: Direct Observation of Radical Cation Intermediates

Giese, Bernd; Napp, Matthias; Jacques, Olivier; Boudebous, Hassen; Taylor, Alexander M.; Wirz, Jakob

doi:10.1002/anie.200500391

Cited by 54 publications

(42 citation statements)

References 33 publications

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“…They show clearly distinct maxima, with 2,4-dimethoxyphenylalanine radical cation absorbing around 450 nm, and 2,4,6-trimethoxyphenylalanine radical cation absorbing around 550 nm (see also ref. [24] ). The maximum of the tyrosyl radical absorption is located at 402 nm.…”

Section: Relay Amino Acidmentioning

confidence: 93%

“…The suitability of this injector for the site-selective oxidation of an aromatic amino acid has been shown previously in oligopeptides where the injector was coupled to an aromatic amino acid at the C-terminus via an ester linkage. [24] In this work, we chose to shorten the linkage between amino acid and injection unit to ensure fast injection and thereby exclude any intra-or intermolecular side reactions of radicals 5 and 6. Alcohol 4 should therefore be directly connected to the aromatic ring of an amino acid side chain via an ether linkage.…”

Section: Electron Acceptormentioning

confidence: 99%

“…[22][23][24] It is based on photoinduced cleavage of a tert-butyl ketone functionality attached to a substituted tetrahydrofuran ring. The resulting radical 5 undergoes heterolytic b-elimination and yields radical cation 6.…”

Section: Electron Acceptormentioning

confidence: 99%

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Development of a Model System for the Study of Long Distance Electron Transfer in Peptides

et al. 2008

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Abstract:We have designed and synthesized a peptide model in which stepwise electron transfer (ET) through amino acid side chains could be observed. An injection system, which generates an electron hole upon laser irradiation, was connected directly to the aromatic side chain of a modified C-terminal amino acid. This electron acceptor could be observed by transient absorption spectroscopy. The N-terminal amino acid tyrosine acts as an electron donor, giving a different signal in the transient absorption spectrum. Additional non-natural oxidizable aromatic amino acids were synthesized as spectroscopic sensors to detect oxidized amino acid side chains as chemical intermediates in long range ET.

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Section: Relay Amino Acidmentioning

confidence: 93%

Section: Electron Acceptormentioning

confidence: 99%

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Development of a Model System for the Study of Long Distance Electron Transfer in Peptides

et al. 2008

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“…McNeill et al (2006a; and Aguzzi et al (2003) established the formation of a "quasi-liquid layer" (QLL) or of an "interface region", respectively, ranging from several tens to 200 nm thickness at 200 K that enabled the practically unlimited uptake of HCl in contrast to the limited uptake on crystalline ice. Advanced quantum-chemical methods fail to reproduce the structure and depth of the QLL of ice whose structure is perturbed owing to contamination by acidic trace gases (Girardet and Toubin, 2001).…”

Section: Trace Gas Uptake On Ice Surfacesmentioning

confidence: 99%

“…A significant body of literature exists on photo-induced charge or energy transfer in organic molecules related to biochemistry and water waste treatment (Canonica et al, 2000(Canonica et al, , 2005Giese et al, 2005). The primary absorbing species (photosensitizer) is excited into a triplet state and depending on the redox properties of available reaction partners and the medium, charge or energy transfer can occur to other molecules.…”

Section: Photochemistry On Atmospheric Surfacesmentioning

confidence: 99%

An overview of current issues in the uptake of atmospheric trace gases by aerosols and clouds

et al. 2010

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Abstract.A workshop was held in the framework of the ACCENT (Atmospheric Composition Change -a European Network) Joint Research Programme on "Aerosols" and the Programme on "Access to Laboratory Data". The aim of the workshop was to hold "Gordon Conference" type discussion covering accommodation and reactive uptake of water vapour and trace pollutant gases on condensed phase atmospheric materials. The scope was to review and define the current state of knowledge of accommodation coefficients for water vapour on water droplet and ice surfaces, and uptake of trace gas species on a variety of different surfaces characteristic of the atmospheric condensed phase particulate matter and cloud droplets. Twenty-six scientists participated in this Correspondence to: C. E. Kolb (kolb@aerodyne.com) meeting through presentations, discussions and the development of a consensus review.In this review we present an analysis of the state of knowledge on the thermal and mass accommodation coefficient for water vapour on aqueous droplets and ice and a survey of current state-of the-art of reactive uptake of trace gases on a range of liquid and solid atmospheric droplets and particles. The review recommends consistent definitions of the various parameters that are needed for quantitative representation of the range of gas/condensed surface kinetic processes important for the atmosphere and identifies topics that require additional research.

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Thyminoxetane als Ladungsfalle zum chemischen Nachweis des Nucleinsäure‐vermittelten Überschusselektronentransfers

Stafforst

Diederichsen

2006

Angewandte Chemie

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Die Wanderung von Elektronen nachweisen: Thyminoxetane ermöglichten es, dank ihres günstigen Redoxpotentials und der schnellen Cycloreversion den Transfer von Überschussladungen in Nucleinsäuren in außergewöhnlich hohen Quantenausbeuten zu verfolgen (siehe Schema; PNA=Peptidnucleinsäure). Untersucht wurde die Distanzabhängigkeit des Ladungstransfers, die typisch für einen Hopping‐Mechanismus ist.

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Multistep Electron Transfer in Oligopeptides: Direct Observation of Radical Cation Intermediates

Cited by 54 publications

References 33 publications

Development of a Model System for the Study of Long Distance Electron Transfer in Peptides

Development of a Model System for the Study of Long Distance Electron Transfer in Peptides

An overview of current issues in the uptake of atmospheric trace gases by aerosols and clouds

Thyminoxetane als Ladungsfalle zum chemischen Nachweis des Nucleinsäure‐vermittelten Überschusselektronentransfers

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