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Synthesis of Mixed Phosphonate Esters and Amino Acid-Based Phosphonamidates, and Their Screening as Herbicides.
Backx, Simon; Desmedt, Willem; Dejaegere, Andreas; Simoens, Andreas; Van de Poel, Jef; Krasowska, Dorota; Audenaert, Kris; Stevens, Christian V; Mangelinckx, Sven.
Afiliación
  • Backx S; SynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium.
  • Desmedt W; Laboratory of Applied Mycology and Phenomics, Department of Plants and Crops, Faculty of Bioscience Engineering, Ghent University, Valentin Vaerwyckweg 1, 9000 Ghent, Belgium.
  • Dejaegere A; Plant Sciences Unit, Flanders Research Institute for Agriculture, Fisheries and Food (ILVO), Burg. van Gansberghelaan 96, 9820 Merelbeke, Belgium.
  • Simoens A; SynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium.
  • Van de Poel J; SynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium.
  • Krasowska D; SynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium.
  • Audenaert K; SynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium.
  • Stevens CV; Laboratory of Applied Mycology and Phenomics, Department of Plants and Crops, Faculty of Bioscience Engineering, Ghent University, Valentin Vaerwyckweg 1, 9000 Ghent, Belgium.
  • Mangelinckx S; SynBioC Research Group, Department of Green Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium.
Int J Mol Sci ; 25(9)2024 Apr 26.
Article en En | MEDLINE | ID: mdl-38731958
ABSTRACT
While organophosphorus chemistry is gaining attention in a variety of fields, the synthesis of the phosphorus derivatives of amino acids remains a challenging task. Previously reported methods require the deprotonation of the nucleophile, complex reagents or hydrolysis of the phosphonate ester. In this paper, we demonstrate how to avoid these issues by employing phosphonylaminium salts for the synthesis of novel mixed n-alkylphosphonate diesters or amino acid-derived n-alkylphosphonamidates. We successfully applied this methodology for the synthesis of novel N-acyl homoserine lactone analogues with varying alkyl chains and ester groups in the phosphorus moiety. Finally, we developed a rapid, quantitative and high-throughput bioassay to screen a selection of these compounds for their herbicidal activity. Together, these results will aid future research in phosphorus chemistry, agrochemistry and the synthesis of bioactive targets.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Ésteres / Organofosfonatos / Aminoácidos / Herbicidas Idioma: En Revista: Int J Mol Sci Año: 2024 Tipo del documento: Article País de afiliación: Bélgica Pais de publicación: Suiza
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Ésteres / Organofosfonatos / Aminoácidos / Herbicidas Idioma: En Revista: Int J Mol Sci Año: 2024 Tipo del documento: Article País de afiliación: Bélgica Pais de publicación: Suiza