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N + PC strategy for the synthesis of phosphinic pseudopeptides incorporating glycine isostere

Sofia Romanovna Golovash 1
Sofia Romanovna Golovash
, 
Alexey Vladimirovich Borodachev 1
Alexey Vladimirovich Borodachev
, 
Maxim E Dmitriev 1
Maxim E Dmitriev
, 
Valery Vladimirovich Ragulin 1
Valery Vladimirovich Ragulin
1 Institute of Physiologically Active Compounds, Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russian Federation
10.1016/j.mencom.2023.10.015
Published 2023-10-18
Communication , Volume 33, Issue 6, 784-785
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Golovash S. R. et al. N + PC strategy for the synthesis of phosphinic pseudopeptides incorporating glycine isostere // Mendeleev Communications. 2023. Vol. 33. No. 6. pp. 784-785.
GOST all authors (up to 50) Copy
Golovash S. R., Borodachev A. V., Dmitriev M. E., Ragulin V. V. N + PC strategy for the synthesis of phosphinic pseudopeptides incorporating glycine isostere // Mendeleev Communications. 2023. Vol. 33. No. 6. pp. 784-785.
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TY - JOUR
DO - 10.1016/j.mencom.2023.10.015
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.015
TI - N + PC strategy for the synthesis of phosphinic pseudopeptides incorporating glycine isostere
T2 - Mendeleev Communications
AU - Golovash, Sofia Romanovna
AU - Borodachev, Alexey Vladimirovich
AU - Dmitriev, Maxim E
AU - Ragulin, Valery Vladimirovich
PY - 2023
DA - 2023/10/18
PB - Mendeleev Communications
SP - 784-785
IS - 6
VL - 33
ER -
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@article{2023_Golovash,
author = {Sofia Romanovna Golovash and Alexey Vladimirovich Borodachev and Maxim E Dmitriev and Valery Vladimirovich Ragulin},
title = {N + PC strategy for the synthesis of phosphinic pseudopeptides incorporating glycine isostere},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Oct},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.015},
number = {6},
pages = {784--785},
doi = {10.1016/j.mencom.2023.10.015}
}
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Golovash, Sofia Romanovna, et al. “N + PC strategy for the synthesis of phosphinic pseudopeptides incorporating glycine isostere.” Mendeleev Communications, vol. 33, no. 6, Oct. 2023, pp. 784-785. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.10.015.

Keywords

amidoalkylation.
dialkyl methylenebiscarbamates
glycine isostere
phosphinic pseudopeptides
phosphonous carboxylic acids

Abstract

The reaction between dialkyl methylenebiscarbamates and phosphonous carboxylic acids affords N-protected phosphinic pseudopeptides incorporating glycine isostere. The compounds obtained are promising building blocks for subsequent peptide modification.

References

.
Synthesis of 1-aminoalkylphosphinic acids. Part 2. An alkylation approach
McCleery P.P., Tuck B.
Journal of the Chemical Society Perkin Transactions 1, 1989
.
Synthesis of the Phosphinic Analogue of Thyrotropin Releasing Hormone
Matziari M., Bauer K., Dive V., Yiotakis A.
Journal of Organic Chemistry, 2008
.
Structure-Guided, Single-Point Modifications in the Phosphinic Dipeptide Structure Yield Highly Potent and Selective Inhibitors of Neutral Aminopeptidases
Vassiliou S., Węglarz-Tomczak E., Berlicki Ł., Pawełczak M., Nocek B., Mulligan R., Joachimiak A., Mucha A.
Journal of Medicinal Chemistry, 2014
.
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
.
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
.
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
.
Phosphinic Peptide Matrix Metalloproteinase-9 Inhibitors by Solid-Phase Synthesis Using a Building Block Approach
Buchardt J., Ferreras M., Krog-Jensen C., Delaissé J., Foged N.T., Meldal M.
Chemistry - A European Journal, 1999