Synthesis of N-peptide-6-amino-D-luciferin conjugates

Anita K. Kovács, Péter Hegyes, Gábor J. Szebeni, Lajos I. Nagy, László G. Puskás, Gábor K. Tóth

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A general strategy for the synthesis of N-peptide-6-amino-D-luciferin conjugates has been developed. The applicability of the strategy was demonstrated with the preparation of a known substrate, N-Z-Asp-Glu-Val-Asp-6-amino-D-luciferin (N-Z-DEVD-aLuc). N-Z-DEVD-aLuc was obtained via a hybrid liquid/solid phase synthesis method, in which the appropriately protected C-terminal amino acid was coupled to 6-amino-2-cyanobenzothiazole and the resulting conjugate was reacted with D-cysteine in order to get the protected amino acid-6-amino-D-luciferin conjugate, which was then attached to resin. The resulting loaded resin was used for the solid-phase synthesis of the desired N-peptide-6-amino-D-luciferin conjugate without difficulties, which was then attested with NMR spectroscopy and LC-MS, and successfully tested in a bioluminescent system.

Original languageEnglish
Article number120
JournalFrontiers in Chemistry
Volume6
Issue numberAPR
DOIs
Publication statusPublished - Apr 1 2018

    Fingerprint

Keywords

  • Aminoluciferin
  • Bioluminescence
  • Conjugate
  • Protease activity
  • Solid-phase peptide synthesis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this