Design and evaluation of analogues of the bacterial cell-wall peptidoglycan motif L-Lys-D-Ala-D-Ala for use in a vancomycin biosensor.

Hernout, Olivier;Berthoin, Karine;Delattre, Isabelle;Tulkens, Paul M.;Marchand-Brynaert, Jacqueline;et.al.
(2007) Bioorganic & Medicinal Chemistry Letters : the tetrahedron journal for research at the interface of chemistry and biology — Vol. 17, n° 21, p. 5758-5762 (2007)

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Authors
  • Hernout, OlivierUCLouvain
    Author
  • Berthoin, KarineUCLouvain
    Author
  • Delattre, IsabelleUCLouvain
    Author
  • Tulkens, Paul M.UCLouvain
    Author
  • Carryn, StéphaneUCLouvain
    Author
  • Marchand-Brynaert, JacquelineUCLouvain
    Author
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Abstract
Four small molecular receptors of vancomycin have been designed to make part of a novel biosensor device based on the FTIR-ATR detection: N-Boc (2a) or N-Ac (2b)-6-aminocaproyl-D-Ala-D-Ala and N-Boc (3a) or N-Ac (3b)-6-aminocaproyl-D-Ala-d-Ser. Using an original microbiological approach to assess the competition of compounds with the natural target of vancomycin in bacteria, EC(50) values of 6.3-8.0 x 10(-5)M (2a-b) and 7.1-9.3 x 10(-4)M (3a-b) were determined. Vancomycin:2b complex was characterized by MS.
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Hernout, O., Berthoin, K., Delattre, I., Tulkens, P. M., Carryn, S., & Marchand-Brynaert, J. (2007). Design and evaluation of analogues of the bacterial cell-wall peptidoglycan motif L-Lys-D-Ala-D-Ala for use in a vancomycin biosensor. Bioorganic & Medicinal Chemistry Letters : the tetrahedron journal for research at the interface of chemistry and biology, 17(21), 5758-5762. https://doi.org/10.1016/j.bmcl.2007.08.055 (Original work published 2007)