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The synthesis of immunomodulating peptide alloferon, the active principle of antiviral drug allokine-alpha

Abstract

Two variants of the synthesis of tridecapeptide alloferon, the active principle of antiviral preparation allokine-alpha, were developed on the basis of fragment condensation in solution or on the Merrifield resin. The solid phase variant of the synthesis was shown to be more technological; it allows the preparation of the product at a higher total yield (40% vs. 17% for conventional synthesis in solution from the starting derivatives of the C-terminal dipeptide). The by-products formed during the synthesis of alloferon were identified.

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Abbreviations

DCM:

dichloromethane

DIEA:

N,N′-diisopropylethylamine

HOBt:

1-hydroxybenzotriazole

HONb:

N-hydroxy-5-norbornene-2,3-dicarboximide

HONp:

p-nitrophenol

MALDI MS:

matrixassisted laser desorption ionization mass spectrometry

NMM:

N-methylmorpholine

(P):

styrene-1% divinylbenzene copolymer

SPS:

solid phase synthesis

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Correspondence to M. V. Sidorova.

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Original Russian Text © M.V. Sidorova, A.S. Molokoedov, E.V. Kudryavtseva, M.I. Baldin, D.A. Frid, M.V. Ovchinnikov, Zh.D. Bespalova, V.N. Bushuev, 2006, published in Bioorganicheskaya Khimiya, 2006, Vol. 32, No. 2, pp. 151–160.

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Sidorova, M.V., Molokoedov, A.S., Kudryavtseva, E.V. et al. The synthesis of immunomodulating peptide alloferon, the active principle of antiviral drug allokine-alpha. Russ J Bioorg Chem 32, 136–145 (2006). https://doi.org/10.1134/S1068162006020051

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  • DOI: https://doi.org/10.1134/S1068162006020051

Key words

  • alloferon
  • peptide synthesis
  • fragment condensation