Peptide stapling by late-stage Suzuki-Miyaura cross-coupling

Gruss, Hendrik
Feiner, Rebecca C.
Mseya, Ridhiwan
Schroeder, David C.
Jewginski, Michat
Mueller, Kristian M.
Latajka, Rafat
Marıon, Antoıne
Sewald, Norbert
The development of peptide stapling techniques to stabilise alpha-helical secondary structure motifs of peptides led to the design of modulators of protein-protein interactions, which had been considered undruggable for a long time. We disclose a novel approach towards peptide stapling utilising macrocyclisation by late-stage Suzuki-Miyaura cross-coupling of bromotryptophan-containing peptides of the catenin-binding domain of axin. Optimisation of the linker length in order to find a compromise between both sufficient linker rigidity and flexibility resulted in a peptide with an increased alpha-helicity and enhanced binding affinity to its native binding partner beta-catenin. An increased proteolytic stability against proteinase K has been demonstrated.


Bioactive Surface Design Based on Functional Composite Electrospun Nanofibers for Biomolecule Immobilization and Biosensor Applications
Uzun, Sema Demirci; Kayaci, Fatma; UYAR, Tamer; TİMUR, SUNA; Toppare, Levent Kamil (2014-04-09)
The combination of nanomaterials and conducting polymers attracted remarkable attention for development of new immobilization matrices for enzymes. Hereby, an efficient surface design was investigated by modifying the graphite rod electrode surfaces with one-step electrospun nylon 6,6 nanofibers or 4% (w/w) multiwalled carbon nanotubes (MWCNTs) incorporating nylon 6,6 nanofibers (nylon 6,6/4MWCNT). High-resolution transmission electron microscopy study confirmed the successful incorporation of the MWCNTs in...
Comonomer effects on binding performances and morphology of acrylate-based imprinted polymers
Tunc, Yeliz; Hasırcı, Nesrin; Yesilada, Akgul; Ulubayram, Kezban (2006-09-20)
The objective of this study was to investigate the effect of different functional groups of molecularly imprinted polymers (MIPs) on the binding characteristics towards a specific template molecule by examining selectivity and recognition processes. Several non-covalent theophylline imprinted polymers (TIPs) were prepared by using only methacrylic acid (MAA), or MAA and 2-hydroxyethyl methacrylate (HEMA) comonomer, or MAA and acrylamide (ACM) comonomer. In all cases, a high amount of ethylene glycol dimetha...
Deactivation model for textural effects on kinetics of gas-solid noncatalytic reactions ''char gasification with CO2''
Yasyerli, N; Doğu, Timur; Dogu, G; Ar, I (1996-06-01)
Variation of the reactivity of a solid reactant due to changes in number of working active sites and pore structure was represented by a deactivation model. The model was shown to give good aggreement with the experimental data obtained for the gasification of chars of different lignites. All the kinetic data obtained at different temperatures (800 degrees-950 degrees C) and also for different types of coals were represented with a single generalized relation. The increase of the surface area of the char at...
Erkoç, Şakir; HALICIOGLU, T; TILLER, WA (1992-08-15)
Energy- and structure-related properties of small gold clusters deposited on the GaAs(110) surface were investigated in this work using a molecular dynamics procedure. A recently developed potential energy function based on two- and three-body interactions was employed in calculating energies and forces. These calculations produced some consistent results with experiments. The three-body interactions involving As atoms in particular, were found to play an important role in determining favorable binding site...
Chemoselective Immobilization of Proteins by Microcontact Printing and Bio-orthogonal Click Reactions
Tolstyka, Zachary P.; Richardson, Wade; Bat, Erhan; Stevens, Caitlin J.; Parra, Dayanara P.; Dozier, Jonathan K.; Distefano, Mark D.; Dunn, Bruce; Maynard, Heather D. (Wiley, 2013-12-16)
Herein, a combination of microcontact printing of functionalized alkanethiols and site-specific modification of proteins is utilized to chemoselectively immobilize proteins onto gold surfaces, either by oxime- or copper-catalyzed alkyne-azide click chemistry. Two molecules capable of click reactions were synthesized, an aminooxy-functionalized alkanethiol and an azide-functionalized alkanethiol, and self-assembled monolayer (SAM) formation on gold was confirmed by IR spectroscopy. The alkanethiols were then...
Citation Formats
H. Gruss et al., “Peptide stapling by late-stage Suzuki-Miyaura cross-coupling,” BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol. 18, pp. 0–0, 2022, Accessed: 00, 2022. [Online]. Available: