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.
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Funding
This work was partly supported by the following Grants: GINOP-2.3.2-15-2016-00030 and GINOP-2.3.2-15-2016-00001 from the National Research, Development and Innovation Office (NKFI), Hungary. Gábor J. Szebeni was supported by János Bolyai Research Scholarship of the Hungarian Academy of Sciences (BO/00139/17/8).
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Conceptualization: László G. Puskás, Investigation: Anita K. Kovács, Péter Hegyes, Gábor J. Szebeni, NMR analysis: Krisztián Bogár, Writing - original draft, review & editing: Anita K. Kovács, Supervision: Gábor K. Tóth.
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Kovács, A.K., Hegyes, P., Szebeni, G.J. et al. Synthesis of N-Peptide-6-Amino-d-Luciferin Conjugates with Optimized Fragment Condensation Strategy. Int J Pept Res Ther 25, 1209–1215 (2019). https://doi.org/10.1007/s10989-018-9768-8
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DOI: https://doi.org/10.1007/s10989-018-9768-8