Synthesis of N-Peptide-6-Amino-d-Luciferin Conjugates with Optimized Fragment Condensation Strategy

Anita K. Kovács, Péter Hegyes, Gábor J. Szebeni, Krisztián Bogár, László G. Puskás, Gábor K. Tóth

Research output: Contribution to journalArticle

Abstract

Abstract: The synthesis of peptide-luciferin conjugates has a pivotal role in the development of bioluminescent detection systems that are based on the determination of protease enzyme activity. This work describes the optimized synthesis of an N-peptide-6-amino-d-luciferin conjugate (Fmoc-Gly-Pro-6-amino-d-luciferin) with a simple fragment condensation method in adequate yields. Fmoc-Gly-Pro-6-amino-d-luciferin was produced from a previously synthesized Fmoc-Gly-Pro-OH and also previously synthesized 6-amino-2-cyanobenzothiazole with an optimized method, to which conjugate cysteine was added in an also improved way. The resulting conjugate was successfully used in a bioluminescent system, in vitro, demonstrating the applicability of the method. Graphical Abstract: [Figure not available: see fulltext.].

Original languageEnglish
Pages (from-to)1209-1215
Number of pages7
JournalInternational Journal of Peptide Research and Therapeutics
Volume25
Issue number3
DOIs
Publication statusPublished - Sep 1 2019

Keywords

  • Aminoluciferin
  • Bioluminescence
  • Conjugate
  • Fragment condensation
  • Protease activity

ASJC Scopus subject areas

  • Analytical Chemistry
  • Bioengineering
  • Biochemistry
  • Molecular Medicine
  • Drug Discovery

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