Search results for: Oliver Seitz

Items from 1 to 20 out of 104 results

article

Towards a templated reaction that translates RNA in cells into a proaptotic peptide‐PNA conjugate

Yannic Altrichter, Peter Bou‐Dib, Christina Kuznia, Oliver Seitz

Journal of Peptide Science > 29 > 7 > n/a - n/a

Nucleic acid‐templated chemistry opens the intriguing prospect of triggering the synthesis of drugs only in diseased cells. Herein, we explore the feasibility of using RNA‐templated chemical reactions for the activation of a known Smac peptidomimetic compound (SMC), which has proapoptotic activity. Two peptide nucleic acid (PNA) conjugates were used to enable conditional activation of a masked SMC...

article

Toward conditional control of Smac mimetic activity by RNA‐templated reduction of azidopeptides on PNA or 2′‐OMe‐RNA

Yannic Altrichter, Justus Schöller, Oliver Seitz

Biopolymers > 112 > 12 > n/a - n/a

Oligonucleotide templated reactions can be used to control the activity of functional molecules based on the presence of a specific trigger sequence. We report an RNA‐controlled reaction system to conditionally restore the N‐terminal amino group and thus binding affinity of azide‐modified Smac mimetic compounds (SMCs) for their target protein X‐linked Inhibitor of Apoptosis Protein (XIAP). Two templated...

article

A Self‐immolative Molecular Beacon for Amplified Nucleic Acid Detection**

Magdalena Roth, Oliver Seitz

Chemistry – A European Journal > 27 > 57 > 14189 - 14194

Fluorogenic hybridization probes allow the detection of RNA and DNA sequences in homogeneous solution. Typically, one target molecule activates the fluorescence of a single probe molecule. This limits the sensitivity of nucleic acid detection. Herein, we report a self‐immolative molecular beacon (iMB) that escapes the one‐target/one‐probe paradigm. The iMB probe includes a photoreductively cleavable...

article

Enabling Cysteine‐Free Native Chemical Ligation at Challenging Junctions with a Ligation Auxiliary Capable of Base Catalysis

Olaf Fuchs, Sebastian Trunschke, Hendrik Hanebrink, Marc Reimann, more

Angewandte Chemie International Edition > 60 > 35 > 19483 - 19490

Ligation auxiliaries are used in chemical protein synthesis to extend the scope of native chemical ligation (NCL) beyond cysteine. However, auxiliary‐mediated ligations at sterically demanding junctions have been difficult. Often the thioester intermediate formed in the thiol exchange step of NCL accumulates because the subsequent S→N acyl transfer is extremely slow. Here we introduce the 2‐mercapto‐2‐(pyridin‐2‐yl)ethyl...

article

Ein zur Basenkatalyse befähigtes Ligationsauxiliar ermöglicht die cysteinfreie native chemische Ligation an anspruchsvollen Verknüpfungsstellen

Olaf Fuchs, Sebastian Trunschke, Hendrik Hanebrink, Marc Reimann, more

Angewandte Chemie > 133 > 35 > 19633 - 19640

Ligationsauxiliare werden in der chemischen Proteinsynthese eingesetzt, um den Anwendungsbereich der nativen chemischen Ligation (NCL) über Cystein hinaus zu erweitern. An sterisch anspruchsvollen Ligationsstellen erweisen sich Auxiliar‐vermittelte Ligationen allerdings als schwierig. Oft akkumuliert das im Thiolaustauschschritt der NCL gebildete Thioester‐Intermediat, da der anschließende S→N‐Acyltransfer...

article

Rational Design of a DNA‐Scaffolded High‐Affinity Binder for Langerin

Gunnar Bachem, Eike‐Christian Wamhoff, Kim Silberreis, Dongyoon Kim, more

Angewandte Chemie International Edition > 59 > 47 > 21016 - 21022

Binders of langerin could target vaccines to Langerhans cells for improved therapeutic effect. Since langerin has low affinity for monovalent glycan ligands, highly multivalent presentation has previously been key for targeting. Aiming to reduce the amount of ligand required, we rationally designed molecularly defined high‐affinity binders based on the precise display of glycomimetic ligands (Glc2NTs)...

article

Rational Design of a DNA‐Scaffolded High‐Affinity Binder for Langerin

Gunnar Bachem, Eike‐Christian Wamhoff, Kim Silberreis, Dongyoon Kim, more

Angewandte Chemie > 132 > 47 > 21202 - 21208

article

Nucleic acid and SNP detection via template‐directed native chemical ligation and inductively coupled plasma mass spectrometry

Pablo Lores Lareo, Michael W. Linscheid, Oliver Seitz

Journal of Mass Spectrometry > 54 > 8 > 676 - 683

Detection of nucleic acids and single nucleotide polymorphisms (SNPs) is of pivotal importance in biology and medicine. Given that the biological effect of SNPs often is enhanced in combination with other SNPs, multiplexed SNP detection is desirable. We show proof of concept of the multiplexed detection of SNPs based on the template‐directed native chemical ligation (NCL) of PNA‐probes carrying a...

article

Templated chemistry for bioorganic synthesis and chemical biology

Oliver Seitz

Journal of Peptide Science > 25 > 7 > n/a - n/a

In light of the 2018 Max Bergmann Medal, this review discusses advancements on chemical biology–driven templated chemistry developed in the author's laboratories. The focused review introduces the template categories applied to orient functional units such as functional groups, chromophores, biomolecules, or ligands in space. Unimolecular templates applied in protein synthesis facilitate fragment...

article

Exploring the Limits of Bivalency by DNA‐Based Spatial Screening

Natali Dubel, Susanne Liese, Franziska Scherz, Oliver Seitz

Angewandte Chemie International Edition > 58 > 3 > 907 - 911

Multivalency can facilitate complex formation when monovalent receptor–ligand interactions are weak. However, enhanced binding of two multivalent binding partners should be avoidable, for example when bivalent receptors ought to utilize multimolecular interactions to cross‐link binding partners. We herein report the first systematic study to assess the criteria deciding whether a bivalent system engages...

article

Untersuchungen zu Grenzen der Bivalenz mit DNA‐basierter räumlicher Rasterung

Natali Dubel, Susanne Liese, Franziska Scherz, Oliver Seitz

Angewandte Chemie > 131 > 3 > 918 - 923

Multivalenz kann eine Komplexbildung ermöglichen, selbst wenn monovalente Ligand/Rezeptor‐Interaktionen schwach sind. Allerdings sollte eine verstärkte Interaktion zweier multivalenter Bindungspartner vermieden werden können, beispielsweise falls bivalente Rezeptoren multimolekulare Wechselwirkungen eingehen, um Bindungspartner zu vernetzen. Hier stellen wir die erste systematische Untersuchung zu...

article

A traceless catch‐and‐release method for rapid peptide purification

Oliver Reimann, Oliver Seitz, Dominik Sarma, Robert Zitterbart

Journal of Peptide Science > 25 > 1 > n/a - n/a

In contrast to peptide synthesis, peptide purification by high performance liquid chromatography (HPLC) cannot be easily varied in number and scale, which results in production restraints. Catch‐and‐release purification of peptides may help to ease HPLC‐related limitations and provides thus an alternative, allowing for fast protocols with great potential for parallelization and scale‐up. This work...

article

Features of Auxiliaries That Enable Native Chemical Ligation beyond Glycine and Cleavage via Radical Fragmentation

Simon F. Loibl, Andre Dallmann, Kathleen Hennig, Carmen Juds, more

Chemistry – A European Journal > 24 > 14 > 3623 - 3633

Native chemical ligation (NCL) is an invaluable tool in the total chemical synthesis of proteins. Ligation auxiliaries overcome the requirement for cysteine. However, the reported auxiliaries remained limited to glycine‐containing ligation sites and the acidic conditions applied for cleavage of the typically applied N‐benzyl‐type linkages promote side reactions. With the aim to improve upon both ligation...

article

Strand Displacement in Coiled‐Coil Structures: Controlled Induction and Reversal of Proximity

Katharina Gröger, Georgina Gavins, Oliver Seitz

Angewandte Chemie International Edition > 56 > 45 > 14217 - 14221

Coiled‐coil peptides are frequently used to create new function upon the self‐assembly of supramolecular complexes. A multitude of coil peptide sequences provides control over the specificity and stability of coiled‐coil complexes. However, comparably little attention has been paid to the development of methods that allow the reversal of complex formation under non‐denaturing conditions. Herein, we...

article

Strand Displacement in Coiled‐Coil Structures: Controlled Induction and Reversal of Proximity

Katharina Gröger, Georgina Gavins, Oliver Seitz

Angewandte Chemie > 129 > 45 > 14405 - 14409

article

A fluorogenic native chemical ligation for assessing the role of distance in peptide-templated peptide ligation

Henrik Petszulat, Oliver Seitz

Bioorganic & Medicinal Chemistry > 2017 > 25 > 18 > 5022-5030

Protein-templated reactions have been used for fragment-based drug discovery as well as for covalent labeling, detection and manipulation of proteins. In spite of the growing interest in protein-templated reactions, little is known about the design criteria. Herein we present a systematic study on the effects of proximity in peptide-templated reactions. To facilitate reaction monitoring at low concentrations...

article

Immobilization methods for the rapid total chemical synthesis of proteins on microtiter plates

Robert Zitterbart, Michael Krumrey, Oliver Seitz

Journal of Peptide Science > 23 > 7-8 > 539 - 548

The chemical synthesis of proteins typically involves the solid‐phase peptide synthesis of unprotected peptide fragments that are stitched together in solution by native chemical ligation (NCL). The process is slow, and throughput is limited because of the need for repeated high performance liquid chromatography purification steps after both solid‐phase peptide synthesis and NCL. With an aim to provide...

article

Parallel Chemical Protein Synthesis on a Surface Enables the Rapid Analysis of the Phosphoregulation of SH3 Domains

Robert Zitterbart, Oliver Seitz

Angewandte Chemie International Edition > 55 > 25 > 7252 - 7256

Analysis of postranslationally modified protein domains is complicated by an availability problem, as recombinant methods rarely allow site‐specificity at will. Although total synthesis enables full control over posttranslational and other modifications, chemical approaches are limited to shorter peptides. To solve this problem, we herein describe a method that combines a) immobilization of N‐terminally...

article

Parallele chemische Proteinsynthese auf der Oberfläche zur schnellen Analyse der Phosphoregulierung von SH3‐Domänen

Robert Zitterbart, Oliver Seitz

Angewandte Chemie > 128 > 25 > 7368 - 7373

Mangelnde Verfügbarkeit erschwert die Analyse posttranslational modifizierter Proteindomänen, denn rekombinante Methoden vermitteln nur selten die gewünschte Ortsspezifität. Die Totalsynthese ermöglicht zwar eine nahezu vollkommene Kontrolle über posttranslationale und andere Modifikationen, jedoch bleiben chemische Methoden auf kürzere Peptide beschränkt. Zur Lösung dieses Problems präsentieren wir...

chapter

Chemical Synthesis of Glycopeptides

Christian Haase, Oliver Seitz

Topics in Current Chemistry > Glycopeptides and Glycoproteins > 1-36

Despite its omnipresence in nature, comparatively little is known about how glycosylation affects the function and activity of proteins. To understand the role of protein glycosylation at the molecular level, it is important to have access to homogeneous glycoproteins and glycopeptides. Chemical synthesis is particularly suited to provide uniform glycoprotein material, thus playing a pivotal role...

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INFONA - science communication portal

Search results for: Oliver Seitz

Towards a templated reaction that translates RNA in cells into a proaptotic peptide‐PNA conjugate

Toward conditional control of Smac mimetic activity by RNA‐templated reduction of azidopeptides on PNA or 2′‐OMe‐RNA

A Self‐immolative Molecular Beacon for Amplified Nucleic Acid Detection**

Enabling Cysteine‐Free Native Chemical Ligation at Challenging Junctions with a Ligation Auxiliary Capable of Base Catalysis

Ein zur Basenkatalyse befähigtes Ligationsauxiliar ermöglicht die cysteinfreie native chemische Ligation an anspruchsvollen Verknüpfungsstellen

Rational Design of a DNA‐Scaffolded High‐Affinity Binder for Langerin

Rational Design of a DNA‐Scaffolded High‐Affinity Binder for Langerin

Nucleic acid and SNP detection via template‐directed native chemical ligation and inductively coupled plasma mass spectrometry

Templated chemistry for bioorganic synthesis and chemical biology

Exploring the Limits of Bivalency by DNA‐Based Spatial Screening

Untersuchungen zu Grenzen der Bivalenz mit DNA‐basierter räumlicher Rasterung

A traceless catch‐and‐release method for rapid peptide purification

Features of Auxiliaries That Enable Native Chemical Ligation beyond Glycine and Cleavage via Radical Fragmentation

Strand Displacement in Coiled‐Coil Structures: Controlled Induction and Reversal of Proximity

Strand Displacement in Coiled‐Coil Structures: Controlled Induction and Reversal of Proximity

A fluorogenic native chemical ligation for assessing the role of distance in peptide-templated peptide ligation

Immobilization methods for the rapid total chemical synthesis of proteins on microtiter plates

Parallel Chemical Protein Synthesis on a Surface Enables the Rapid Analysis of the Phosphoregulation of SH3 Domains

Parallele chemische Proteinsynthese auf der Oberfläche zur schnellen Analyse der Phosphoregulierung von SH3‐Domänen

Chemical Synthesis of Glycopeptides

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