Efficient Site‐Selective Immobilization of Aldehyde‐Tagged Peptides and Proteins by Knoevenagel Ligation

Janson N, Heinks T, Beuel T, Alam S, Höhne M, Bornscheuer UT, Fischer von Mollard G, Sewald N (2021)
ChemCatChem.

Zeitschriftenaufsatz | E-Veröff. vor dem Druck | Englisch
 
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Abstract / Bemerkung
The aldehyde tag is appropriate to selectively label proteins, prepare antibody-drug conjugates or to immobilize enzymes or antibodies for biotechnological and medical applications. The cysteine within the consensus sequence CxPxR of the aldehyde tag is specifically oxidized by the formylglycine-generating enzyme (FGE) to the non-canonical and electrophilic amino acid C-alpha-formylglycine (FGly). Subsequent reductive amination is a common method for site-directed immobilization, which usually results in poor immobilization efficiency due to the reaction conditions. Here, we introduce a new solid support like agarose modified with an aryl substituted pyrazolone (Knoevenagel reagent) that was obtained in a facile and efficient 2-step synthesis. The modified agarose allowed the site-selective and efficient immobilization of aldehyde-containing small molecules, peptides and proteins - in particular enzymes - at physiological pH (6.2-8.2) without any additive or catalyst needed. In comparison to reductive amination, higher loadings and activities were achieved in various buffers at different concentrations and temperatures.
Erscheinungsjahr
2021
Zeitschriftentitel
ChemCatChem
ISSN
1867-3880
eISSN
1867-3899
Finanzierungs-Informationen
Open-Access-Publikationskosten wurden durch die Universität Bielefeld im Rahmen des DEAL-Vertrags gefördert.
Page URI
https://pub.uni-bielefeld.de/record/2959858

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Janson N, Heinks T, Beuel T, et al. Efficient Site‐Selective Immobilization of Aldehyde‐Tagged Peptides and Proteins by Knoevenagel Ligation. ChemCatChem. 2021.
Janson, N., Heinks, T., Beuel, T., Alam, S., Höhne, M., Bornscheuer, U. T., Fischer von Mollard, G., et al. (2021). Efficient Site‐Selective Immobilization of Aldehyde‐Tagged Peptides and Proteins by Knoevenagel Ligation. ChemCatChem. https://doi.org/10.1002/cctc.202101485
Janson, Nils, Heinks, Tobias, Beuel, Tobias, Alam, Sarfaraz, Höhne, Matthias, Bornscheuer, Uwe T., Fischer von Mollard, Gabriele, and Sewald, Norbert. 2021. “Efficient Site‐Selective Immobilization of Aldehyde‐Tagged Peptides and Proteins by Knoevenagel Ligation”. ChemCatChem.
Janson, N., Heinks, T., Beuel, T., Alam, S., Höhne, M., Bornscheuer, U. T., Fischer von Mollard, G., and Sewald, N. (2021). Efficient Site‐Selective Immobilization of Aldehyde‐Tagged Peptides and Proteins by Knoevenagel Ligation. ChemCatChem.
Janson, N., et al., 2021. Efficient Site‐Selective Immobilization of Aldehyde‐Tagged Peptides and Proteins by Knoevenagel Ligation. ChemCatChem.
N. Janson, et al., “Efficient Site‐Selective Immobilization of Aldehyde‐Tagged Peptides and Proteins by Knoevenagel Ligation”, ChemCatChem, 2021.
Janson, N., Heinks, T., Beuel, T., Alam, S., Höhne, M., Bornscheuer, U.T., Fischer von Mollard, G., Sewald, N.: Efficient Site‐Selective Immobilization of Aldehyde‐Tagged Peptides and Proteins by Knoevenagel Ligation. ChemCatChem. (2021).
Janson, Nils, Heinks, Tobias, Beuel, Tobias, Alam, Sarfaraz, Höhne, Matthias, Bornscheuer, Uwe T., Fischer von Mollard, Gabriele, and Sewald, Norbert. “Efficient Site‐Selective Immobilization of Aldehyde‐Tagged Peptides and Proteins by Knoevenagel Ligation”. ChemCatChem (2021).
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2022-06-30T13:19:41Z
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