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  1. IPB Halle
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    • Research Mission and Profile
    • Trenner 0
    • Molecular Signal Processing
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        • Symbiosis Signaling
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    • Biochemistry of Plant Interactions
      • Secretariat & All Staff
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Gulyas-Fekete, G.; Boluda, C. J.; Westermann, B.; Wessjohann, L. A.; Anti-Friedel-Crafts-Type Substitution To Form Biaryl Linkages Synthesis 45 3038-3043 (2013) DOI: 10.1055/s-0033-1339682
  • Abstract
  • BibText
  • RIS

The ipso-substitution of one (or two) hydroxy groups of phloroglucinol with arene nucleophiles (e.g., o-xylene, tetralin, biphenyl) can be achieved easily under Friedel–Crafts-type conditions with or without the use of organic solvents affording a variety of 3,5-dihydroxybiphenyls (57–89% yields). The new method has significant practical advantages compared to classical biaryl-­coupling routes.

Publications

Sproß, J.; Brauch, S.; Mandel, F.; Wagner, M.; Buckenmaier, S.; Westermann, B.; Sinz, A.; Multidimensional nano-HPLC coupled with tandem mass spectrometry for analyzing biotinylated proteins Anal. Bioanal. Chem. 405 2163-2173 (2013) DOI: 10.1007/s00216-012-6057-9
  • Abstract
  • BibText
  • RIS

Multidimensional high-performance liquid chromatography (HPLC) is a key method in shotgun proteomics approaches for analyzing highly complex protein mixtures by complementary chromatographic separation principles. Here, we describe an integrated 3D-nano-HPLC/nano-electrospray ionization quadrupole time-of-flight mass spectrometry system that allows an enzymatic digestion of proteins followed by an enrichment and subsequent separation of the created peptide mixtures. The online 3D-nano-HPLC system is composed of a monolithic trypsin reactor in the first dimension, a monolithic affinity column with immobilized monomeric avidin in the second dimension, and a reversed phase C18 HPLC-Chip in the third dimension that is coupled to a nano-ESI-Q-TOF mass spectrometer. The 3D-LC/MS setup is exemplified for the identification of biotinylated proteins from a simple protein mixture. Additionally, we describe an online 2D-nano-HPLC/nano-ESI-LTQ-Orbitrap-MS/MS setup for the enrichment, separation, and identification of cross-linked, biotinylated species from chemical cross-linking of cytochrome c and a calmodulin/peptide complex using a novel trifunctional cross-linker with two amine-reactive groups and a biotin label.

Publications

Westermann, B.; Dörner, S.; Brauch, S.; Schaks, A.; Heinke, R.; Stark, S.; van Delft, F. L.; van Berkel, S. S.; CuAAC-mediated diversification of aminoglycoside–arginine conjugate mimics by non-reducing di- and trisaccharides Carbohyd. Res. 371 61-67 (2013) DOI: 10.1016/j.carres.2013.02.003
  • Abstract
  • BibText
  • RIS

Di- and triguanidinylation of trehalose, sucrose, and melizitose has been achieved via a Huisgen-cycloaddition approach. They can serve as aminoglycoside–arginine conjugate mimics, which has been demonstrated by their biological profiles in assays against Bacillus subtilis. For comparative studies, tetraguanidinylated neamine and kanamycin derivatives have also been synthesized and evaluated

Publications

Brauch, S.; van Berkel, S. S.; Westermann, B.; Higher-order multicomponent reactions: beyond four reactants Chem. Soc. Rev. 42 4948-4962 (2013) DOI: 10.1039/C3CS35505E
  • Abstract
  • BibText
  • RIS

Multicomponent reactions (MCRs) are by far the most successful class of reactions leading to high structural diversity and molecular complexity through a single transformation. As part of the ongoing search for pharmacologically active lead structures, the obtained structural diversity allows for the fast exploration of a large chemical space. Not surprisingly, the development of MCRs, leading to new structural frameworks or serving as key transformations in the total synthesis of natural products, has expanded rapidly over the last few decades. To date a multitude of new three- and four-component reactions have already been described; however, examples of “higher-order” MCRs where five or even more components are combined in a single reaction vessel are remarkably scarce. This tutorial review aims to critically describe the developments achieved in recent years, charting the ideas, challenges, and milestone reactions that were essential for the progress of this field.

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