HFIP vermittelt eine direkte C‐C‐Kupplung zwischen Michael‐Akzeptoren und Eschenmosersalz

Lemmerer, Miran; Riomet, Margaux; Meyrelles, Ricardo; Maryasin, Boris; González, Leticia; Maulide, Nuno

doi:10.1002/ange.202109933

Angewandte Chemie

2022

DOI: 10.1002/ange.202109933

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HFIP vermittelt eine direkte C‐C‐Kupplung zwischen Michael‐Akzeptoren und Eschenmosersalz

Miran Lemmerer

Margaux Riomet

Ricardo Meyrelles

et al.

Abstract: Ein direkter C‐C‐Kupplungsprozess, bei dem Michael‐Akzeptoren und Eschenmosersalz zusammengeführt werden, wird vorgestellt. Obwohl er an die Morita‐Baylis‐Hillman‐Reaktion erinnert, benötigt dieser Prozess keinen Lewis‐Base‐Katalysator. Der zugrundeliegende Mechanismus konnte durch eine Kombination aus kinetischen Isotopenmarkierungsexperimenten und computergestützten Untersuchungen aufgeklärt werden, die die kritische Rolle von HFIP als überlegenem Mediator für Protonentransferschritte sowie die entscheidende… Show more

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Cited by 4 publications

References 49 publications

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The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection

Antón-Cánovas

Alonso

2022

Angewandte Chemie

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C-H bond formylation is the most immediate way to incorporate the versatile formyl group into (hetero)aromatics. However, the type of reagents and severe conditions involved in the classical formylation methods often curtail their application, especially in the presence of other functional groups. Herein, we present the Eschenmoser's salt, a commercially available (dimethylamino)methylating chemical, as a useful reagent for the C-H formylation of indolizines and other compounds. The method is straightforward and mild, furnishing indolizinecarbaldehydes in modest-to-good yields with exclusive and remote regioselectivity. Furthermore, these compounds can be easily transformed into pushpull dyes and are highly selective in the colorimetric detection of nitrite, a substance extensively employed as preservative in the food industry, the concentration of which is crucial to control to prevent harmful effects in living organisms. The assay is simple, allowing the naked-eye detection of nitrite in solution or on a cotton swab for a wide range of concentrations.

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The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection

Antón-Cánovas

Alonso

2022

Angewandte Chemie

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Peptide Stapling by Crosslinking Two Amines with α‐Ketoaldehydes through Diverse Modified Glyoxal‐Lysine Dimer Linkers

Guo,

Chu,

et al. 2024

Angewandte Chemie

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α‐Ketoaldehydes play versatile roles in the ubiquitous natural processes of protein glycation. However, leveraging the reactivity of α‐ketoaldehydes for biomedical applications has been challenging. Previously, the reactivity of α‐ketoaldehydes with guanidine has been harnessed to design probes for labeling Arg residues on proteins in an aqueous medium. Herein, a highly effective, broadly applicable, and operationally simple protocol for stapling native peptides by crosslinking two amino groups through diverse imidazolium linkers with various α‐ketoaldehyde reagents is described. The use of hexafluoroisopropanol as a solvent facilitates rapid and clean reactions under mild conditions and enables unique selectivity for Lys over Arg. The naturally occurring GOLD/MOLD linkers have been expanded to encompass a wide range of modified glyoxal‐lysine dimer (OLD) linkers. In a proof‐of‐concept trial, these modular stapling reactions enabled a convenient two‐round strategy to streamline the structure‐activity relationship (SAR) study of the wasp venom peptide anoplin, leading to enhanced biological activities.

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The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection

Antón-Cánovas

Alonso

2022

Angew Chem Int Ed

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HFIP vermittelt eine direkte C‐C‐Kupplung zwischen Michael‐Akzeptoren und Eschenmosersalz

Cited by 4 publications

References 49 publications

The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection

The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection

Peptide Stapling by Crosslinking Two Amines with α‐Ketoaldehydes through Diverse Modified Glyoxal‐Lysine Dimer Linkers

The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection

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