Organic Synthesis and Biological Signal Transduction

Hinterding, Klaus; Alonso-Díaz, Daniel; Waldmann, Herbert

doi:10.1002/(sici)1521-3773(19980403)37:6<688::aid-anie688>3.0.co;2-b

Cited by 135 publications

(1 citation statement)

References 208 publications

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“…The second class of self-assembling peptide molecules reviewed in this section is peptide amphiphiles (PAs),also called lipidated peptides or lipopeptides, which are composed of two main regions, ahydrophobic alkyl tail and ahydrophilic peptide sequence. These molecules are naturally present in living organisms, which have important roles asinitiators in the signal transduction pathways [117,118] and in the host defence mechanisms of bacteria [119]. The lipidic parts of these molecules are believed to take part in protein-protein and protein-lipid interactions and provide a link to the cellular membrane [118].…”

Section: Peptide Amphiphilesmentioning

confidence: 99%

Self-assembled peptide nanostructures for functional materials

et al. 2016

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Nature is an important inspirational source for scientists, and presents complex and elegant examples of adaptive and intelligent systems created by self-assembly. Significant effort has been devoted to understanding these sophisticated systems. The self-assembly process enables us to create supramolecular nanostructures with high order and complexity, and peptide-based self-assembling building blocks can serve as suitable platforms to construct nanostructures showing diverse features and applications. In this review, peptide-based supramolecular assemblies will be discussed in terms of their synthesis, design, characterization and application. Peptide nanostructures are categorized based on their chemical and physical properties and will be examined by rationalizing the influence of peptide design on the resulting morphology and the methods employed to characterize these high order complex systems. Moreover, the application of self-assembled peptide nanomaterials as functional materials in information technologies and environmental sciences will be reviewed by providing examples from recently published high-impact studies.

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Section: Peptide Amphiphilesmentioning

confidence: 99%

Self-assembled peptide nanostructures for functional materials

et al. 2016

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Optimization in organic synthesis

Snieckus

1999

Med. Res. Rev.

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Art is always a bonus to synthesis . . . . the artistic aspect of synthesis, beautiful and marvelous as it is, should not be a justification for carrying out a total synthesis. If your problem is truly essential then you don't care about the elegance. The more essential your first E is, the less important your last E becomes." 1 "Will we be able to recapture the many millions of presumed 'transient'natural products that were evolutionarily de-selected along the paths that eventually led to the natural products synthesized on Earth today? . . . I cannot imagine that in a young synthetic chemist's lifetime, it will not be accomplished." 2 Organic Synthesis, quo vadis? 3 has been a phrase, perhaps in a more modern language, on the lips of the practitioners of this demanding science-art, undoubtedly from the earliest times 4 but more vigorously in the last two decades. 5 Comparison of achievements of yesterday 6 and today 7 suggests progress in our abilities to construct molecules of complexity, with higher stereocontrol, faster analysis, and greater prediction of eventual success. However, the practical aspects, on any scale, of brevity, efficiency, safety, eco-consciousness, and energy-and resource-frugality remain, as noted by a major synthetic craftsman, 8 crudely addressed. The Y2K symbolism is perhaps also appropriate for urgently dedicating our efforts to making headway in the solution of these interrelated goals.Our central science 5a progresses on fronts of method development and total synthesis with a great deal of cross-talk and interdependency (see Fig. 1). The burgeoning literature of new methods suggests that 70% are not repeated, perhaps even in the original laboratories, a situation with dire consequences for ascertaining true yield ranges and reproducibility a la the Org. Syn. religion. Furthermore, as judged from a cursory glance of tables in recent journals, much is left to be desired in giving confidence to the user that a method has generality (substrate diversity, FG and steric tolerance, catalyst or reagent minimization, and temperature and solvent optimization). Although the beauty of judiciously modeled use of PGs is to be applauded, 9 FG protection is a continuing embarrassment and annoyance. Synthetic chemists are challenging the dogma by daring the multi-FG molecules to behave in the manner desired. Ugi multicomponent reactions 10 and combinatorial synthesis 11 will undoubtedly soon influence the PG-expediency problem. In industry, statistical programs 12 at times drive optimization of reactions thus meeting the normal intense time constraints to produce mulit-kg of commercial substances.Atom-economy, a term coined by another influential synthetic chemist, 13 has brought awareness of an issue to academic scientists which their industrial process and development colleagues un-

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Synthese und In-vitro-Evaluierung des Ras-Farnesyltransferase-Inhibitors Pepticinnamin E

Hinterding¹,

Hagenbuch²,

Rétey³

et al. 1998

Angewandte Chemie

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Ein modular aufgebauter Bisubstratinhibitor ist die natürlich vorkommende Titelverbindung (rechts gezeigt), die nun erstmals synthetisiert wurde. Bei In‐vitro‐Assays hemmte sie das Enzym Farnesyltransferase sowohl bezüglich eines Peptidsubtrats als auch bezüglich des Farnesylpyrophosphats (KI = 30 bzw. 8 μM). Die Inhibierung wird wesentlich durch die zentrale Tripeptideinheit und die absolute Konfiguration der darin enthaltenen nichtproteinogenen Aminosäure bestimmt.

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Organic Synthesis and Biological Signal Transduction

Cited by 135 publications

References 208 publications

Self-assembled peptide nanostructures for functional materials

Self-assembled peptide nanostructures for functional materials

Optimization in organic synthesis

Synthese und In-vitro-Evaluierung des Ras-Farnesyltransferase-Inhibitors Pepticinnamin E

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