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Solid phase isotope exchange with spillover hydrogen in amino acids, peptides, and proteins

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Abstract

We summarize here information on the theoretical and experimental study of high-temperature (150–200°C) solid phase catalytic isotope exchange (HSCIE) carried out with amino acids, peptides, and proteins under the action of spillover hydrogen. Main specific features of the HSCIE reaction, its mechanism, and its use for studying spatial interactions in polypeptides are discussed. A virtually complete absence of racemization makes this reaction a valuable preparative method. The main regularities of the HSCIE reaction with the participation of spillover tritium have been revealed in the case of peptides and proteins, and the dependence of reactivity of peptide fragments on the spatial organization of their molecules has been studied. An important peculiarity of this reaction is that HSCIE proceeds at 150–200°C with a high degree of chirality retention in amino acids and peptides. This is provided by its reaction mechanism, which consists in a synchronous one-center substitution at the saturated carbon atom characterized by the formation of pentacoordinated carbon and a three-center bond between the carbon and the incoming and outgoing hydrogen atoms.

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Abbreviations

BAC:

Bronsted acid type center

HSCIE:

high-temperature solid phase catalytic isotope exchange

Ctx G1:

α-conotoxin

SH:

spillover hydrogen

TS:

transition state

Zrv IIB:

zervamycin IIB.

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Authors and Affiliations

  1. Institute of Molecular Genetics, Russian Academy of Sciences, pl. Kurchatova 2, 123182, Moscow, Russia

    Yu. A. Zolotarev & A. K. Dadayan

  2. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, 119991, Moscow, Russia

    Yu. A. Borisov

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  1. Yu. A. Zolotarev
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Translated from Bioorganicheskaya Khimiya, Vol. 31, No. 1, 2005, pp. 3–21.

Original Russian Text Copyright © 2005 by Zolotarev, Dadayan, Borisov.

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Zolotarev, Y.A., Dadayan, A.K. & Borisov, Y.A. Solid phase isotope exchange with spillover hydrogen in amino acids, peptides, and proteins. Russ J Bioorg Chem 31, 1–17 (2005). https://doi.org/10.1007/s11171-005-0001-0

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