Synthesis of Phosphinic Analogue of Alanylleucine

Abstract

The amidoalkylation reactions of a phosphonous acid containing a structural isostere of leucine in acetyl chloride and(or) acetic anhydride were studied under conditions of acid catalysis. A two-component method for the synthesis of a phosphinic analogue of alanylleucine using ethylidenebis(benzylcarbamate) was proposed.

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Funding

This work was performed as part of the governmental task of the Institute of Physiologically Active Substances of the Russian Academy of Sciences for 2019 (topic no. 00902019-008) with partial financial support from the Presidium of the Russian Academy of Sciences no. 14P, the Russian Foundation for Basic Research (grants no. 18-03-00959, 18-03-01123) and the Russian Science Foundation (grant no. 19-13-00294, chromatographic, spectral and elemental analysis).

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Correspondence to V. V. Ragulin.

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Golovash, S.R., Grigorkevich, O.S., Tsebrikova, G.S. et al. Synthesis of Phosphinic Analogue of Alanylleucine. Russ J Gen Chem 90, 753–756 (2020). https://doi.org/10.1134/S1070363220040313

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Keywords:

  • pseudo-alanylleucine
  • matrix metalloproteinases (MMPs)
  • zinc metalloproteinase inhibitors
  • amidoalkylation
  • phosphinic structural isosteres