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

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

A facile solid-phase synthetic method for incorporating the imidazoline ring motif, a surrogate for a <i>trans</i> 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 c...

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Bibliographic Details
Main Authors: Krzysztof Kaczmarek, Barbara Pacholczyk-Sienicka, Łukasz Albrecht, Janusz Zabrocki, Ronald J. Nachman
Format: Article
Language:English
Published: MDPI AG 2021-05-01
Series:Molecules
Subjects:
insect neuropeptides
pyrokinins
<i>trans</i> peptide bond
imidazoline ring
SPOS
Online Access:https://www.mdpi.com/1420-3049/26/11/3271
Description
Summary:A facile solid-phase synthetic method for incorporating the imidazoline ring motif, a surrogate for a <i>trans</i> 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).
ISSN:1420-3049

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