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Convenient Preparation of t-Butyl Nα-Protected Amino Acid Esters from t-Butanol

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Abstract

A preparation of t-butyl esters of Nα-protected amino acid is described that Nα-P proceeds from protected amino acids and t-butanol using anhydrous magnesium sulfate and an excess of boron trifluoride diethyl etherate as additional reagents. The method affords t-butyl esters in good yields and a variety of amino acid side chains and substituents tolerate the reaction conditions.

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ACKNOWLEDGMENTS

The authors are grateful to Dr. Alexey K. Surin (Protein Research Institute RAS) for his generous support with mass-spectra acquisition.

Funding

This work was supported by the State assignment of Ministry of Science and Higher Education of the Russian Federation (2019 0101-2019-0014).

Author information

Authors and Affiliations

  1. Branch of Shemyakin–Ovchinnikov Bioorganic Chemistry Institute RAS, 142290, Pushchino, Moscow oblast, Russia

    V. N. Azev & A. N. Chulin

  2. Istitute for Theoretical and Experimental Biophysics RAS, 142290, Pushchino, Moscow oblast, Russia

    M. V. Molchanov

  3. Shemyakin–Ovchinnikov Bioorganic Chemistry Institute RAS, 117997, Moscow, Russia

    A. I. Miroshnikov

Authors
  1. V. N. Azev
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  2. A. N. Chulin
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  3. M. V. Molchanov
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  4. A. I. Miroshnikov
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Corresponding author

Correspondence to V. N. Azev.

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The authors declare that they have no conflicts of interest.

This article does not contain any studies involving animals or human participants performed by any of the authors.

Additional information

Abbreviations: APCI, atmospheric pressure chemical ionization; Fm, 9-fluorenylmethyl; Hep, heptane; In, indole; Palm, Palmytoil.

The article is dedicated to the memory of Professor Vadim T. Ivanov, Academician, RAS.

Corresponding author: phone: +7 (496) 773-54-42.

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Azev, V.N., Chulin, A.N., Molchanov, M.V. et al. Convenient Preparation of t-Butyl Nα-Protected Amino Acid Esters from t-Butanol. Russ J Bioorg Chem 49, 524–528 (2023). https://doi.org/10.1134/S1068162023030056

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  • DOI: https://doi.org/10.1134/S1068162023030056

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