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

Kovács, Anita and Hegyes, Péter and Szebeni, Gábor J. and Nagy, Lajos I. and Puskás, László G. and Tóth, Gábor J. (2018) Synthesis of N-peptide-6-amino-D-luciferin Conjugates. Frontiers in Chemistry. ISSN 2296-2646

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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.

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