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Papainkatalysierte kinetisch kontrollierte Peptidsynthese. Verwendung von Alkylestern des Arginins als Aminokomponente

Papain-catalyzed kinetically controlled peptide synthesis. The use of arginine esters as amino component

  • Organische Chemie Und Biochemie
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Summary

The papain-catalyzed reaction of esters of Z-alanine with various arginine esters was investigated. Using H-Arg-OPr i as a nucleophile the expected dipeptide product results in high yield. Otherwise, reactions with arginine esters of primary alkohols provide products undergoing further reactions. This allows the synthesis of N-protected peptide esters containing two or more arginine residues in a one-step reaction. The influence of reaction conditions on the process was investigated.

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Authors and Affiliations

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

    Volker Schellenberger, Ute Schellenberger & Hans-Dieter Jakubke

  2. Institut für Eiweißforschung, Akademie der Wissenschaften der UdSSR, SU-142292, Pushchino, Moskau, UdSSR

    Yuri V. Mitin

Authors
  1. Volker Schellenberger
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  2. Ute Schellenberger
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  3. Yuri V. Mitin
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  4. Hans-Dieter Jakubke
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Abkürzungen

Die IUPAC/IUB-Regeln für Aminosäure- und Peptidderivate wurden befolgt; vgl. Eur. J. Biochem.53, 1 (1975). Die verwendeten Aminosäuren hatten (L)-Konfiguration.-Glo-Gly-OH=Glykolylglycinester,-OCam=Carboxamidomethylester, -OBu i=Isobutylester,-OMe=Methylester,-OPr i=Isopropylester,Z=Benzyloxycarbonyl.

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Schellenberger, V., Schellenberger, U., Mitin, Y.V. et al. Papainkatalysierte kinetisch kontrollierte Peptidsynthese. Verwendung von Alkylestern des Arginins als Aminokomponente. Monatsh Chem 120, 437–443 (1989). https://doi.org/10.1007/BF00811555

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  • DOI: https://doi.org/10.1007/BF00811555

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