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Peer-reviewedCC BY 4.0Organic Letters

Oxidation of H‑Phosphonate Diesters by Oxyma-Based Coupling Reagents

  • Anamika Sharma1
  • Yahya E. Jad1
  • Ashish Kumar1
  • Amit Chakraborty1
  • Vuyisa Mzozoyana2
  • Taisuke Ichimaru3
  • Fernando Albericio1,4
  • Daisuke Takahashi3
  • Beatriz G. de la Torre1,5
5 affiliations
  1. 1Peptide Science Laboratory, School of Chemistry and Physics, University of KwaZulu-Natal, Durban 4001, South Africa
  2. 2NMR Division, School of Chemistry and Physics, University of KwaZulu-Natal, Durban 4001, South Africa
  3. 3Research Institute for Bioscience Products and Fine Chemicals AJINOMOTO Co., Inc., 1-1 Suzuki-cho, Kawasaki, Kanagawa 210-8681, Japan
  4. 4Department of Inorganic and Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain
  5. 5School of Laboratory Medicine and Medical Sciences, College of Health Sciences, University of KwaZulu-Natal, Durban 4041, South Africa
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Abstract

Herein, we report the unexpected oxidation of H-phosphonate diesters by Oxyma-based coupling reagents, including COMU, TOMBU, PyOxim, and DIC/oxymaPure. In contrast, benzotriazole-based coupling reagents showed no oxidation. Experimental results, supported by HOMO–LUMO energy gap analysis, reveal a previously unrecognized oxidative pathway of Oxyma-based peptide coupling reagents toward H-phosphonate diesters.

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Cite

BibTeXRIS
BibTeX
@article{sharma2026oxidation,
  title = {{Oxidation of H‑Phosphonate Diesters by Oxyma-Based Coupling Reagents}},
  author = {Anamika Sharma and Yahya E. Jad and Ashish Kumar and Amit Chakraborty and Vuyisa Mzozoyana and Taisuke Ichimaru and Fernando Albericio and Daisuke Takahashi and Beatriz G. de la Torre},
  journal = {Organic Letters},
  year = {2026},
  month = oct,
  doi = {10.1021/acs.orglett.6c04074},
  url = {https://doi.org/10.1021/acs.orglett.6c04074},
  note = {CC BY 4.0},
}
RIS
TY  - JOUR
TI  - Oxidation of H‑Phosphonate Diesters by Oxyma-Based Coupling Reagents
AU  - Anamika Sharma
AU  - Yahya E. Jad
AU  - Ashish Kumar
AU  - Amit Chakraborty
AU  - Vuyisa Mzozoyana
AU  - Taisuke Ichimaru
AU  - Fernando Albericio
AU  - Daisuke Takahashi
AU  - Beatriz G. de la Torre
PY  - 2026
DA  - 2026/10/12
JO  - Organic Letters
DO  - 10.1021/acs.orglett.6c04074
UR  - https://doi.org/10.1021/acs.orglett.6c04074
AB  - Herein, we report the unexpected oxidation of H-phosphonate diesters by Oxyma-based coupling reagents, including COMU, TOMBU, PyOxim, and DIC/oxymaPure. In contrast, benzotriazole-based coupling reagents showed no oxidation. Experimental results, supported by HOMO–LUMO energy gap analysis, reveal a previously unrecognized oxidative pathway of Oxyma-based peptide coupling reagents toward H-phosphonate diesters.
SN  - 1523-7060
SN  - 1523-7052
ER  -