Russian Journal of Bioorganic Chemistry

, Volume 31, Issue 1, pp 1–17 | Cite as

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

  • Yu. A. Zolotarev
  • A. K. Dadayan
  • Yu. A. Borisov
Review Articles
Received:
Revised:

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.

Key words

amino acids isotope hydrogen exchange peptides proteins quantum chemical calculations solid phase reactions spillover hydrogen 

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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Copyright information

© MAIK “Nauka/Interperiodica” 2005

Authors and Affiliations

  • Yu. A. Zolotarev
    • 1
  • A. K. Dadayan
    • 1
  • Yu. A. Borisov
    • 2
  1. 1.Institute of Molecular GeneticsRussian Academy of SciencesMoscowRussia
  2. 2.Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussia

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