Insight into β-hairpin stability: a structural and thermodynamic study of diastereomeric β-hairpin mimeticsElectronic supplementary information (ESI) available: temperature and concentration-dependent chemical shifts and melting curves of the investigated molecules in different solvents and details of the X-ray analysis. See http://www.rsc.org/suppdata/nj/b1/b111241d/

Erdélyi, Máté; Langer, Vratislav; Karlén, Anders; Gogoll, Adolf

doi:10.1039/b111241d

Cited by 22 publications

(22 citation statements)

References 80 publications

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“…Temperature coefficients (Δ δ /Δ T ) offer a qualitative measure of the involvement of amide protons in intramolecular hydrogen bonding and thus an additional insight into peptide secondary structures 13a. As expected, the temperature coefficients obtained for the solution of compound 1 in dimethyl sulfoxide (Table 1) were consistent with a folded β‐hairpin structure in which the amide protons of Leu‐9 and Ile‐7 are intramolecularly hydrogen bonded and Thr‐4 is in equilibrium between hydrogen‐bonded and nonbonded states 17.…”

Section: Resultsmentioning

confidence: 99%

A New Tool in Peptide Engineering: A Photoswitchable Stilbene‐type β‐Hairpin Mimetic

Erdélyi

Karlén

Gogoll

2005

Chemistry A European J

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Peptide secondary structure mimetics are important tools in medicinal chemistry, as they provide analogues of endogenous peptides with new physicochemical and pharmacological properties. The development, synthesis, photochemical investigation, and conformational analysis of a stilbene-type beta-hairpin mimetic capable of light-triggered conformational changes have been achieved. In addition to standard spectroscopic techniques (nuclear Overhauser effects, amide temperature coefficients, circular dichroism spectroscopy), the applicability of self-diffusion measurements (longitudinal eddy current delay pulsed-field gradient spin echo (LED-PGSE) NMR technique) in conformational studies of oligopeptides is demonstrated. The title compound shows photoisomerization of the stilbene chromophore, resulting in a change in solution conformation between an unfolded structure and a folded beta-hairpin.

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Section: Resultsmentioning

confidence: 99%

A New Tool in Peptide Engineering: A Photoswitchable Stilbene‐type β‐Hairpin Mimetic

Erdélyi

Karlén

Gogoll

2005

Chemistry A European J

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“…[84] Gogoll and co-workers later utilized these protocols in a rapid domino Sonogashira sequence to synthesize amino ester 6 (Scheme 7). [85] Essentially the same experimental protocol was employed by Vollhardt and co-workers to synthesize o-dipropynylated arene 8, which served as the precursor to tribenzocyclyne 9 through an alkyne metathesis reaction (Scheme 8). [86] In this case the Sonogashira reaction was carried out in a prepressurized (ca.…”

Section: Sonogashira Reactionsmentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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Although fire is now rarely used in synthetic chemistry, it was not until Robert Bunsen invented the burner in 1855 that the energy from this heat source could be applied to a reaction vessel in a focused manner. The Bunsen burner was later superseded by the isomantle, oil bath, or hot plate as a source for applying heat to a chemical reaction. In the past few years, heating and driving chemical reactions by microwave energy has been an increasingly popular theme in the scientific community. This nonclassical heating technique is slowly moving from a laboratory curiosity to an established technique that is heavily used in both academia and industry. The efficiency of “microwave flash heating” in dramatically reducing reaction times (from days and hours to minutes and seconds) is just one of the many advantages. This Review highlights recent applications of controlled microwave heating in modern organic synthesis, and discusses some of the underlying phenomena and issues involved.

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“…Typische Bedingungen für die Kupplung von Aryliodiden, ‐bromiden, ‐chloriden und ‐triflaten sind Diethylamin als Base und [PdCl 2 (PPh 3 ) 2 ] (2–5 Mol‐%) als Katalysator mit CuI (5 Mol‐%) als Additiv in DMF 84. Diese Methode wurde von Gogoll et al später in einer schnellen Domino‐Sonogashira‐Sequenz zur Synthese des Aminoesters 6 genutzt (Schema ) 85…”

Section: Literaturüberblickunclassified

Kontrolliertes Erhitzen mit Mikrowellen in der modernen organischen Synthese

Kappe

2004

Angewandte Chemie

246

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Die offene Flamme konnte erst gezielt als Heizquelle für Reaktionsgefäße in der Synthesechemie verwendet werden, nachdem Robert Bunsen 1855 den nach ihm benannten Brenner erfunden hatte. Der Bunsen‐Brenner wurde später durch den Heizpilz, das Ölbad und die Heizplatte als Wärmequellen für chemische Reaktionen abgelöst. In den vergangenen Jahren ist das Erhitzen und Beschleunigen chemischer Reaktionen durch Mikrowellenenergie populär geworden. Diese Heiztechnik hat sich von einer Laborkuriosität zu einer etablierten Methode entwickelt, die an Universitäten und in der Industrie stark genutzt wird. Die effiziente Verringerung der Reaktionszeiten (von Tagen und Stunden auf Minuten und Sekunden) ist nur einer der vielen Vorteile des schnellen Erhitzens mit Mikrowellen (“microwave flash heating”). Dieser Aufsatz gibt einen Überblick über neuere Anwendungen des kontrollierten Mikrowellenerhitzens in der modernen organischen Synthese und diskutiert einige grundlegende Vorgänge.

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Cited by 22 publications

References 80 publications

A New Tool in Peptide Engineering: A Photoswitchable Stilbene‐type β‐Hairpin Mimetic

A New Tool in Peptide Engineering: A Photoswitchable Stilbene‐type β‐Hairpin Mimetic

Controlled Microwave Heating in Modern Organic Synthesis

Kontrolliertes Erhitzen mit Mikrowellen in der modernen organischen Synthese

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