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

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/s...

Full description

Bibliographic Details
Main Authors: Anita K. Kovács, Péter Hegyes, Gábor J. Szebeni, Lajos I. Nagy, László G. Puskás, Gábor K. Tóth
Format: Article
Language:English
Published: Frontiers Media S.A. 2018-04-01
Series:Frontiers in Chemistry
Subjects:
Online Access:http://journal.frontiersin.org/article/10.3389/fchem.2018.00120/full
_version_ 1818558658607316992
author 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
author_facet 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
author_sort Anita K. Kovács
collection DOAJ
description 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.
first_indexed 2024-12-14T00:15:10Z
format Article
id doaj.art-4a64002744cc4ede98484c6aac365ebf
institution Directory Open Access Journal
issn 2296-2646
language English
last_indexed 2024-12-14T00:15:10Z
publishDate 2018-04-01
publisher Frontiers Media S.A.
record_format Article
series Frontiers in Chemistry
spelling doaj.art-4a64002744cc4ede98484c6aac365ebf2022-12-21T23:25:34ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462018-04-01610.3389/fchem.2018.00120333161Synthesis of N-peptide-6-amino-D-luciferin ConjugatesAnita K. Kovács0Anita K. Kovács1Péter Hegyes2Gábor J. Szebeni3Gábor J. Szebeni4Lajos I. Nagy5László G. Puskás6László G. Puskás7Gábor K. Tóth8Department of Medical Chemistry, University of Szeged, Szeged, HungaryAvidin Ltd., Szeged, HungaryAvidin Ltd., Szeged, HungaryAvidin Ltd., Szeged, HungaryDepartment of Genetics, Biological Research Center, Hungarian Academy of Sciences, Szeged, HungaryAvidin Ltd., Szeged, HungaryAvidin Ltd., Szeged, HungaryDepartment of Genetics, Biological Research Center, Hungarian Academy of Sciences, Szeged, HungaryDepartment of Medical Chemistry, University of Szeged, Szeged, HungaryA 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.http://journal.frontiersin.org/article/10.3389/fchem.2018.00120/fullbioluminescenceaminoluciferinconjugateprotease activitysolid-phase peptide synthesis
spellingShingle 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
Synthesis of N-peptide-6-amino-D-luciferin Conjugates
Frontiers in Chemistry
bioluminescence
aminoluciferin
conjugate
protease activity
solid-phase peptide synthesis
title Synthesis of N-peptide-6-amino-D-luciferin Conjugates
title_full Synthesis of N-peptide-6-amino-D-luciferin Conjugates
title_fullStr Synthesis of N-peptide-6-amino-D-luciferin Conjugates
title_full_unstemmed Synthesis of N-peptide-6-amino-D-luciferin Conjugates
title_short Synthesis of N-peptide-6-amino-D-luciferin Conjugates
title_sort synthesis of n peptide 6 amino d luciferin conjugates
topic bioluminescence
aminoluciferin
conjugate
protease activity
solid-phase peptide synthesis
url http://journal.frontiersin.org/article/10.3389/fchem.2018.00120/full
work_keys_str_mv AT anitakkovacs synthesisofnpeptide6aminodluciferinconjugates
AT anitakkovacs synthesisofnpeptide6aminodluciferinconjugates
AT peterhegyes synthesisofnpeptide6aminodluciferinconjugates
AT gaborjszebeni synthesisofnpeptide6aminodluciferinconjugates
AT gaborjszebeni synthesisofnpeptide6aminodluciferinconjugates
AT lajosinagy synthesisofnpeptide6aminodluciferinconjugates
AT laszlogpuskas synthesisofnpeptide6aminodluciferinconjugates
AT laszlogpuskas synthesisofnpeptide6aminodluciferinconjugates
AT gaborktoth synthesisofnpeptide6aminodluciferinconjugates