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Synthese von N-geschütztem Eledoisin (6–11)-Hexapeptid unter Verwendung von Proteasen als Biokatalysatoren

Synthesis of N-protected eledoisin (6–11)-hexapeptide using proteases as biocatalysts

  • Organische Chemie Und Biochemie
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Abstract

Papain and α-chymotrypsin were used for the protease-catalyzed assembly ofBoc-protected eledoisin (6−11)-hexapeptide by (2+4)- and (3+3)-segment condensation, respectively, in aqueous-organic solvent systems. As C-components, chemically synthesizedBoc-protected peptide methyl esters were employed. The nucleophilic tetrapeptide amide was prepared by papain-catalyzed (2+2)-segment coupling, while theZ-protected C-terminal dipeptide amide could be obtained by α-chymotrypsin- and thermolysin-catalyzed peptide bond formation. In addition, the influence of various reaction conditions, such as solvent composition, nucleophile concentration and reaction time, on the yield of theBoc-protected eledoisin (6−11)-hexapeptide was determined.

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Authors and Affiliations

  1. Sektion Biowissenschaften, Bereich Biochemie, Karl-Marx-Universität, DDR-7010, Leipzig, Deutsche Demokratische Republik

    Peter Kuhl, Günter Döring & Hans-Dieter Jakubke

  2. Sektion Biowissenschaften, Martin-Luther-Universität, DDR-4020, Halle (Saale), Deutsche Demokratische Republik

    Klaus Neubert

Authors
  1. Peter Kuhl
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  2. Günter Döring
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  3. Klaus Neubert
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  4. Hans-Dieter Jakubke
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Additional information

Abkürzungen: Es wurden die IUPAC/IUB-Regeln für Aminosäure- und Peptidderivate befolgt; vgl. Eur. J. Biochem.53, 1 (1975). Die verwendeten Aminosäuren hatten mit Ausnahme von GlycinL-Konfiguration.Boc=tetr-Butyloxycarbonyl-,Z=Benzyloxycarbonyl-,Ac=Acetyl-, −OMe=Methylester.

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Kuhl, P., Döring, G., Neubert, K. et al. Synthese von N-geschütztem Eledoisin (6–11)-Hexapeptid unter Verwendung von Proteasen als Biokatalysatoren. Monatsh Chem 115, 423–430 (1984). https://doi.org/10.1007/BF00810003

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  • DOI: https://doi.org/10.1007/BF00810003

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