Academic Bibliography

 Search 200 years of publications by Ghent University researchers.
Advanced search
1 file | 3.02 MB
Add to list
  1. Search results
  2. Synthesis of mixed phosphonate esters...

Synthesis of mixed phosphonate esters and amino acid-based phosphonamidates, and their screening as herbicides

Simon Backx (UGent) , Willem Desmedt (UGent) , Andreas Dejaegere (UGent) , Andreas Simoens (UGent) , Jef Van de Poel, Dorota Krasowska (UGent) , Kris Audenaert (UGent) , Christian Stevens (UGent) and Sven Mangelinckx (UGent)
(2024) INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES. 25(9).
Author
Organization
Project
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.
Keywords
phosphorus chemistry, phosphonamidates, amino acids, AHLs, herbicides, HOMOSERINE LACTONES, BIOLOGICAL EVALUATION, SECONDARY-AMINES, NUCLEOPHILICITIES, PRODRUGS, REACTIVITIES, ANTAGONISTS, INHIBITION

Downloads

  • Download
    IJMS - full text.pdf
    • full text (Published version)
    • |
    • open access
    • |
    • PDF
    • |
    • 3.02 MB

Citation

Please use this url to cite or link to this publication:

MLA
Backx, Simon, et al. “Synthesis of Mixed Phosphonate Esters and Amino Acid-Based Phosphonamidates, and Their Screening as Herbicides.” INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, vol. 25, no. 9, 2024, doi:10.3390/ijms25094739.
APA
Backx, S., Desmedt, W., Dejaegere, A., Simoens, A., Van de Poel, J., Krasowska, D., … Mangelinckx, S. (2024). Synthesis of mixed phosphonate esters and amino acid-based phosphonamidates, and their screening as herbicides. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 25(9). https://doi.org/10.3390/ijms25094739
Chicago author-date
Backx, Simon, Willem Desmedt, Andreas Dejaegere, Andreas Simoens, Jef Van de Poel, Dorota Krasowska, Kris Audenaert, Christian Stevens, and Sven Mangelinckx. 2024. “Synthesis of Mixed Phosphonate Esters and Amino Acid-Based Phosphonamidates, and Their Screening as Herbicides.” INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES 25 (9). https://doi.org/10.3390/ijms25094739.
Chicago author-date (all authors)
Backx, Simon, Willem Desmedt, Andreas Dejaegere, Andreas Simoens, Jef Van de Poel, Dorota Krasowska, Kris Audenaert, Christian Stevens, and Sven Mangelinckx. 2024. “Synthesis of Mixed Phosphonate Esters and Amino Acid-Based Phosphonamidates, and Their Screening as Herbicides.” INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES 25 (9). doi:10.3390/ijms25094739.
Vancouver
1.
Backx S, Desmedt W, Dejaegere A, Simoens A, Van de Poel J, Krasowska D, et al. Synthesis of mixed phosphonate esters and amino acid-based phosphonamidates, and their screening as herbicides. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES. 2024;25(9).
IEEE
[1]
S. Backx et al., “Synthesis of mixed phosphonate esters and amino acid-based phosphonamidates, and their screening as herbicides,” INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, vol. 25, no. 9, 2024.
@article{01HWYT61H2VJZ2R0Z8BSTQPJVR,
  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.}},
  articleno    = {{4739}},
  author       = {{Backx, Simon and Desmedt, Willem and Dejaegere, Andreas and Simoens, Andreas and Van de Poel, Jef and Krasowska, Dorota and Audenaert, Kris and Stevens, Christian and Mangelinckx, Sven}},
  issn         = {{1661-6596}},
  journal      = {{INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES}},
  keywords     = {{phosphorus chemistry,phosphonamidates,amino acids,AHLs,herbicides,HOMOSERINE LACTONES,BIOLOGICAL EVALUATION,SECONDARY-AMINES,NUCLEOPHILICITIES,PRODRUGS,REACTIVITIES,ANTAGONISTS,INHIBITION}},
  language     = {{eng}},
  number       = {{9}},
  pages        = {{15}},
  title        = {{Synthesis of mixed phosphonate esters and amino acid-based phosphonamidates, and their screening as herbicides}},
  url          = {{http://doi.org/10.3390/ijms25094739}},
  volume       = {{25}},
  year         = {{2024}},
}
Altmetric
View in Altmetric
Web of Science
Times cited: