Solid-Phase Synthesis of an Insect Pyrokinin Analog Incorporating an Imidazoline Ring as Isosteric Replacement of a trans Peptide Bond

A facile solid-phase synthetic method for incorporating the imidazoline ring motif, a surrogate for a trans peptide bond, into bioactive peptides is reported. The example described is the synthesis of an imidazoline peptidomimetic analog of an insect pyrokinin neuropeptide via a cyclization reaction...

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Autores principales: Kaczmarek, Krzysztof, Pacholczyk-Sienicka, Barbara, Albrecht, Łukasz, Zabrocki, Janusz, Nachman, Ronald J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8198379/
https://www.ncbi.nlm.nih.gov/pubmed/34071640
http://dx.doi.org/10.3390/molecules26113271
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author Kaczmarek, Krzysztof
Pacholczyk-Sienicka, Barbara
Albrecht, Łukasz
Zabrocki, Janusz
Nachman, Ronald J.
author_facet Kaczmarek, Krzysztof
Pacholczyk-Sienicka, Barbara
Albrecht, Łukasz
Zabrocki, Janusz
Nachman, Ronald J.
author_sort Kaczmarek, Krzysztof
collection PubMed
description A facile solid-phase synthetic method for incorporating the imidazoline ring motif, a surrogate for a trans peptide bond, into bioactive peptides is reported. The example described is the synthesis of an imidazoline peptidomimetic analog of an insect pyrokinin neuropeptide via a cyclization reaction of an iminium salt generated from the preceding amino acid and 2,4-diaminopropanoic acid (Dap).
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spelling pubmed-81983792021-06-14 Solid-Phase Synthesis of an Insect Pyrokinin Analog Incorporating an Imidazoline Ring as Isosteric Replacement of a trans Peptide Bond Kaczmarek, Krzysztof Pacholczyk-Sienicka, Barbara Albrecht, Łukasz Zabrocki, Janusz Nachman, Ronald J. Molecules Communication A facile solid-phase synthetic method for incorporating the imidazoline ring motif, a surrogate for a trans peptide bond, into bioactive peptides is reported. The example described is the synthesis of an imidazoline peptidomimetic analog of an insect pyrokinin neuropeptide via a cyclization reaction of an iminium salt generated from the preceding amino acid and 2,4-diaminopropanoic acid (Dap). MDPI 2021-05-28 /pmc/articles/PMC8198379/ /pubmed/34071640 http://dx.doi.org/10.3390/molecules26113271 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Kaczmarek, Krzysztof
Pacholczyk-Sienicka, Barbara
Albrecht, Łukasz
Zabrocki, Janusz
Nachman, Ronald J.
Solid-Phase Synthesis of an Insect Pyrokinin Analog Incorporating an Imidazoline Ring as Isosteric Replacement of a trans Peptide Bond
title Solid-Phase Synthesis of an Insect Pyrokinin Analog Incorporating an Imidazoline Ring as Isosteric Replacement of a trans Peptide Bond
title_full Solid-Phase Synthesis of an Insect Pyrokinin Analog Incorporating an Imidazoline Ring as Isosteric Replacement of a trans Peptide Bond
title_fullStr Solid-Phase Synthesis of an Insect Pyrokinin Analog Incorporating an Imidazoline Ring as Isosteric Replacement of a trans Peptide Bond
title_full_unstemmed Solid-Phase Synthesis of an Insect Pyrokinin Analog Incorporating an Imidazoline Ring as Isosteric Replacement of a trans Peptide Bond
title_short Solid-Phase Synthesis of an Insect Pyrokinin Analog Incorporating an Imidazoline Ring as Isosteric Replacement of a trans Peptide Bond
title_sort solid-phase synthesis of an insect pyrokinin analog incorporating an imidazoline ring as isosteric replacement of a trans peptide bond
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8198379/
https://www.ncbi.nlm.nih.gov/pubmed/34071640
http://dx.doi.org/10.3390/molecules26113271
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