Frontiers in Chemistry (Apr 2018)

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

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

DOI
https://doi.org/10.3389/fchem.2018.00120
Journal volume & issue
Vol. 6

Abstract

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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.

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