2. Academic Validation
  3. Synthesis of N-peptide-6-amino-D-luciferin Conjugates

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

  • Front Chem. 2018 Apr 19;6:120. doi: 10.3389/fchem.2018.00120.
Anita K Kovács 1 2,  Péter Hegyes 2,  Gábor J Szebeni 2 3,  Lajos I Nagy 2,  László G Puskás 2 3,  Gábor K Tóth 1
Affiliations

Affiliations

  • 1 Department of Medical Chemistry, University of Szeged, Szeged, Hungary.
  • 2 Avidin Ltd., Szeged, Hungary.
  • 3 Department of Genetics, Biological Research Center, Hungarian Academy of Sciences, Szeged, Hungary.
PMID: 29725588 DOI: 10.3389/fchem.2018.00120
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.

Keywords

aminoluciferin; bioluminescence; conjugate; protease activity; solid-phase peptide synthesis.

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