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

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

JOURNAL=Frontiers in Chemistry

VOLUME=6

YEAR=2018

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2018.00120

DOI=10.3389/fchem.2018.00120

ISSN=2296-2646

ABSTRACT=<p>A general strategy for the synthesis of <italic>N</italic>-peptide-6-amino-D-luciferin conjugates has been developed. The applicability of the strategy was demonstrated with the preparation of a known substrate, <italic>N</italic>-Z-Asp-Glu-Val-Asp-6-amino-D-luciferin (<italic>N</italic>-Z-DEVD-aLuc). <italic>N</italic>-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 <italic>N</italic>-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.</p>