Erick M. Carreira


Last Name

Carreira

First Name

Erick M.

ORCID

0000-0003-1472-490X

Organisational unit

03511 - Carreira, Erick M. / Carreira, Erick M.

Search Results

Publications 1 - 10 of 347
  • A novel strategy for bioconjugation
    Item type: Journal Article
    Zumbühl, Andreas; Stano, Pasquale; Sohrmann, Marc; et al. (2007)
    Organic & biomolecular chemistry
  • Platform Reagents Enable Synthesis of Ligand-Directed Covalent Probes: Study of Cannabinoid Receptor 2 in Live Cells
    Item type: Journal Article
    Kosar, Miroslav; Sykes, David A.; Viray, Alexander E.G.; et al. (2023)
    Journal of the American Chemical Society
    Pharmacological modulation of cannabinoid receptor type 2 (CB₂R) holds promise for the treatment of neuroinflammatory disorders, such as Alzheimer’s disease. Despite the importance of CB₂R, its expression and downstream signaling are insufficiently understood in disease- and tissue-specific contexts. Herein, we report the first ligand-directed covalent (LDC) labeling of CB₂R enabled by a novel synthetic strategy and application of platform reagents. The LDC modification allows visualization and study of CB₂R while maintaining its ability to bind other ligands at the orthosteric site. We employed in silico docking and molecular dynamics simulations to guide probe design and assess the feasibility of LDC labeling of CB₂R. We demonstrate selective, covalent labeling of a peripheral lysine residue of CB2R by exploiting fluorogenic O-nitrobenzoxadiazole (O-NBD)-functionalized probes in a TR-FRET assay. The rapid proof-of-concept validation with O-NBD probes inspired incorporation of advanced electrophiles suitable for experiments in live cells. To this end, novel synthetic strategies toward N-sulfonyl pyridone (N-SP) and N-acyl-N-alkyl sulfonamide (NASA) LDC probes were developed, which allowed covalent delivery of fluorophores suitable for cellular studies. The LDC probes were characterized by a radioligand binding assay and TR-FRET experiments. Additionally, the probes were applied to specifically visualize CB₂R in conventional and imaging flow cytometry as well as in confocal fluorescence microscopy using overexpressing and endogenously expressing microglial live cells.
  • Aryl Azocyclopropeniums: Minimalist, Visible-Light Photoswitches
    Item type: Journal Article
    Fink, Moritz; Stäuble, Jannik; Weisgerber, Maite; et al. (2024)
    Journal of the American Chemical Society
    We report convenient syntheses of aryl azocyclopropeniums and a study of their photochemical properties. Incorporation of the smallest arene leads to pronounced redshift of the pi-pi* absorbance band, compared to azobenzenes. Photoisomerization under purple or green light irradiation affords Z- or E-isomers in ratios up to 94% Z or 90% E, and the switches proved stable over multiple irradiation cycles. Thermal half-lives of metastable Z-isomers range from minutes to hours in acetonitrile and water. These properties together with the concise, versatile syntheses render aryl azocyclopropeniums exciting additions to the tool kit of readily available molecular photoswitches for wide ranging applications.
  • Iridium-catalyzed synthesis of primary allylic amines from allylic alcohols
    Item type: Journal Article
    Defieber, Christian; Ariger, Martin A.; Moriel, Patricia; et al. (2007)
    Angewandte Chemie. International Edition
  • Aqueous Instability of δ-Fluorobutylpiperidines
    Item type: Journal Article
    Vorberg, Raffael; Carreira, Erick M.; Müller, Klaus (2017)
    ChemMedChem
  • Apoc Social: A Mobile Interactive and Social Learning Platform for Collaborative Solving of Advanced Problems in Organic Chemistry
    Item type: Journal Article
    Sievertsen, Niels; Carreira, Erick M. (2018)
    Chimia
  • Picolinamides and Iodoalkynes Enable Palladium-Catalyzed syn-Aminoalkynylation of Di- and Trisubstituted Alkenes to Give Pyrrolidines
    Item type: Journal Article
    Müller, Nicolas; Schreib, Benedikt S.; Leutenegger, Sebastian U.; et al. (2022)
    Angewandte Chemie. International Edition
    Palladium-catalyzed aminoalkynylation of electronically unbiased olefins with iodoalkynes is reported. The picolinamide auxiliary enables for the first time the syn-selective aminoalkynylation of mono-, di- and trisubstituted alkenes to afford the corresponding pyrrolidines in up to 97 % yield and as single diastereomers. Furthermore, through a C-H activation approach, the picolinamide allows the rapid synthesis of functionalized olefins, which are suitable cyclization precursors. Facile and orthogonal deprotection of the amides and (SiPr3)-Pr-i-acetylenes in the products, and a subsequent Pictet-Spengler reaction is demonstrated.
  • 2,6-diazaspiro[3.3]heptanes
    Item type: Journal Article
    Burkhard, Johannes; Carreira, Erick M. (2008)
    Organic Letters
  • Journal of the American Chemical Society: A Look Back at 2022 and Forward to 2023
    Item type: Other Journal Item
    Carreira, Erick M. (2023)
    Journal of the American Chemical Society
  • Mn- and Co-Catalyzed Aminocyclizations of Unsaturated Hydrazones Providing a Broad Range of Functionalized Pyrazolines
    Item type: Journal Article
    Balkenhohl, Moritz; Koelbl, Sebastian; Georgiev, Tony; et al. (2021)
    JACS Au
    Manganese- and cobalt-catalyzed aminocyclization reactions of unsaturated hydrazones are reported. Whereas manganese catalysis provides access to pyrazoline and tetrahydropyridazine alcohols, cobalt catalysis for the first time paves the way for the selective formation of pyrazoline aldehydes. Furthermore, various functional groups including hydroperoxide, thiol derivatives, iodide, and bicyclopentane may be introduced via manganese-catalyzed ring-forming aminofunctionalization. A progesterone receptor antagonist was prepared using the aminocyclization protocol.
Publications 1 - 10 of 347