Monatshefte für Chemie / Chemical Monthly

, Volume 113, Issue 4, pp 457–473 | Cite as

Herstellung von Argininpeptiden mitN7,N8-(1,2-Dihydroxycyclohex-1,2-ylen)-Schutz

Ein Beitrag zur Reaktion von 1,2-Cyclohexandion mit Arginin und Lysin
  • Ulrich Hevelke
  • Josef Föhles
  • Jean Knott
  • Helmut Zahn
Organische Chemie Und Biochemie

Synthesis of arginine peptides with N7, N8-(1,2-dihydroxycyclo-hex-1,2-ylene)-protection. Studies on the reaction of 1,2-cyclohexandione with arginine and lysine

Abstract

A method for the synthesis of arginine peptides is described, in which the side chain guanidine function is blocked through reaction with 1,2-cyclohexanedione in borate buffers.

Coupling to the carboxyl group of arginine was achieved by active ester, by dicyclohexylcarbodiimide/1-hydroxybenzotriazole1, and by the mixed anhydride methods2. Neither lactam formation nor acylation of the vicinal hydroxyls of the N7, N8-(1,2-dihydroxycyclohex-1,2-ylene) guanidino group was observed.

Removal of the protecting group is strongly influenced by steric factors. Some side reactions observed during modification of peptides and protein fragments with 1,2-cyclohexanedione are also described.

Keywords

Activation, lactam-formation, side-reactions N7,N8-(1,2-Dihydroxycyclohex-1,2-ylen)-arginine-derivatives and -peptides Semisynthesis 

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Copyright information

© Springer-Verlag 1982

Authors and Affiliations

  • Ulrich Hevelke
    • 1
  • Josef Föhles
    • 1
  • Jean Knott
    • 1
  • Helmut Zahn
    • 1
  1. 1.Deutsches WollforschungsinstitutRheinisch Westfälische Technische Hochschule AachenAachenBundesrepublik Deutschland

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