Home / Articles / Lactone motif in amidoalkylation of (2-carboxyalkyl)hydrophosphinic acids and a new one-pot synthesis of pseudotripeptides

Lactone motif in amidoalkylation of (2-carboxyalkyl)hydrophosphinic acids and a new one-pot synthesis of pseudotripeptides

Dmitry E Ivanov 1
Dmitry E Ivanov
, 
Sofia R Vakulenko 1
Sofia R Vakulenko
, 
Alexey Vladimirovich Borodachev 1
Alexey Vladimirovich Borodachev
, 
Maxim Eduardovich Dmitriev 1
Maxim Eduardovich Dmitriev
, 
Valery Vladimirovich Ragulin 1
Valery Vladimirovich Ragulin
10.71267/mencom.8073
Published 23 September 2026
Communication
0
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Ivanov D. E. et al. Lactone motif in amidoalkylation of (2-carboxyalkyl)hydrophosphinic acids and a new one-pot synthesis of pseudotripeptides // Mendeleev Communications. 2026.
GOST all authors (up to 50)
Copy cite
Ivanov D. E., Vakulenko S. R., Borodachev A. V., Dmitriev M. E., Ragulin V. V. Lactone motif in amidoalkylation of (2-carboxyalkyl)hydrophosphinic acids and a new one-pot synthesis of pseudotripeptides // Mendeleev Communications. 2026.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.71267/mencom.8073
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.8073
TI - Lactone motif in amidoalkylation of (2-carboxyalkyl)hydrophosphinic acids and a new one-pot synthesis of pseudotripeptides
T2 - Mendeleev Communications
AU - Ivanov, Dmitry E
AU - Vakulenko, Sofia R
AU - Borodachev, Alexey Vladimirovich
AU - Dmitriev, Maxim Eduardovich
AU - Ragulin, Valery Vladimirovich
PY - 2026
DA - 2026/09/23
PB - Mendeleev Communications
ER -
BibTex
Cite this
BibTex (up to 50 authors)
Copy cite
@article{2026_Ivanov,
author = {Dmitry E Ivanov and Sofia R Vakulenko and Alexey Vladimirovich Borodachev and Maxim Eduardovich Dmitriev and Valery Vladimirovich Ragulin},
title = {Lactone motif in amidoalkylation of (2-carboxyalkyl)hydrophosphinic acids and a new one-pot synthesis of pseudotripeptides},
journal = {Mendeleev Communications},
year = {2026},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.8073},
doi = {10.71267/mencom.8073}
}
Views / Visits
49 / 49

Keywords

amidoalkylation
organophosphorus compounds
peptide synthesis
phosphinic pseudopeptides
phosphinic pseudotripeptides
phospholactones
Reaction mechanism

Abstract

Amidoalkylation of (2-carboxyalkyl)hydrophosphinic acids proceeds through the formation and subsequent transformation of mixed anhydrides (phospholactones) such as tricoordinated P-lactone, pentacoordinated P-lactone (phosphorane) and then tetracoordinated P-lactone. The obtained results open up the possibility for the effective activation of the terminal carboxylic function of phosphinic dipeptides. A new one-pot approach to the synthesis of pseudotripeptides is proposed by combining amidoalkylation of (2-carboxyalkyl)hydrophosphinic acids with the subsequent peptide synthesis.

Funders

Russian Science Foundation
23-23-00158

References

1.
Phosphinic peptides as zinc metalloproteinase inhibitors
Dive V., Georgiadis D., Matziari M., Makaritis A., Beau F., Cuniasse P., Yiotakis A.
Cellular and Molecular Life Sciences, 2004
3.
Phosphinic Peptides as Potent Inhibitors of Zinc-Metalloproteases
Georgiadis D., Dive V.
Topics in Current Chemistry, 2014
4.
1-Aminoalkylphosphonous acids. Part 1. Isosteres of the protein amino acids
Baylis E.K., Campbell C.D., Dingwall J.G.
Journal of the Chemical Society Perkin Transactions 1, 1984
5.
Synthesis of 1-aminoalkylphosphinic acids. Part 2. An alkylation approach
McCleery P.P., Tuck B.
Journal of the Chemical Society Perkin Transactions 1, 1989
9.
Golovash S.R., Borodachev A.V., Dmitriev M.E., Ragulin V.V.
Mendeleev Communications, 2023
10.
Golovash Sofia Romanovna, Ivanov Dmitry E, Borodachev Alexey Vladimirovich, Simonov Sergey V, Dmitriev Maxim E, Ragulin Valery Vladimirovich
Mendeleev Communications, 2025
11.
Mechanism of Phosphorus–Carbon Bond Formation in the Amidoalkylation of Phosphonous Carboxylic Acids
Dmitriev M.E., Golovash S.R., Borodachev A.V., Ragulin V.V.
Journal of Organic Chemistry, 2020
12.
A Carbodiimide-Mediated P–C Bond-Forming Reaction: Mild Amidoalkylation of P-Nucleophiles by Boc-Aminals
Kokkala P., Rajeshkumar T., Mpakali A., Stratikos E., Vogiatzis K.D., Georgiadis D.
Organic Letters, 2021
15.
Synthesis of energetic compounds bearing a (3,4-dinitro-1H-pyrazol-1-yl)-NNO-azoxy group
Konnov A.A., Dubrovin I.M., Klenov M.S., Anikin O.V., Churakov A.M., Strelenko Y.A., Pivkina A.N., Tartakovsky V.A.
Russian Chemical Bulletin, 2021
17.
Chemoselective Protection of Solid-Phase Compatible Fmoc-Phosphinic Building Blocks
Nasopoulou M., Matziari M., Dive V., Yiotakis A.
Journal of Organic Chemistry, 2006
18.
Optimization and Structure–Activity Relationships of Phosphinic Pseudotripeptide Inhibitors of Aminopeptidases That Generate Antigenic Peptides
Kokkala P., Mpakali A., Mauvais F., Papakyriakou A., Daskalaki I., Petropoulou I., Kavvalou S., Papathanasopoulou M., Agrotis S., Fonsou T., van Endert P., Stratikos E., Georgiadis D.
Journal of Medicinal Chemistry, 2016