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

Russian Journal of Bioorganic Chemistry volume 32, pages 136–145 (2006)Cite this article

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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Authors and Affiliations

  1. Federal Agency on Healthcare and Social Development, Cardiological Research and Production Association, Tret’ya Cherepkovskaya ul. 15a, Moscow, 121552, Russia

    M. V. Sidorova, A. S. Molokoedov, M. V. Ovchinnikov, Zh. D. Bespalova & V. N. Bushuev

  2. ZAO Peptide Synthesis, Moscow, Russia

    E. V. Kudryavtseva, M. I. Baldin & D. A. Frid

Authors
  1. M. V. Sidorova
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  2. A. S. Molokoedov
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  3. E. V. Kudryavtseva
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  4. M. I. Baldin
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  5. D. A. Frid
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  6. M. V. Ovchinnikov
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  7. Zh. D. Bespalova
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  8. V. N. Bushuev
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Corresponding author

Correspondence to M. V. Sidorova.

Additional information

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