Kaczmarek, K.; Pacholczyk-Sienicka, B.; Albrecht, Ł.; Zabrocki, J.; Nachman, R.J. Solid-Phase Synthesis of an Insect Pyrokinin Analog Incorporating an Imidazoline Ring as Isosteric Replacement of a Trans Peptide Bond. Molecules 2021, 26, 3271, doi:10.3390/molecules26113271.
Kaczmarek, K.; Pacholczyk-Sienicka, B.; Albrecht, Ł.; Zabrocki, J.; Nachman, R.J. Solid-Phase Synthesis of an Insect Pyrokinin Analog Incorporating an Imidazoline Ring as Isosteric Replacement of a Trans Peptide Bond. Molecules 2021, 26, 3271, doi:10.3390/molecules26113271.
Kaczmarek, K.; Pacholczyk-Sienicka, B.; Albrecht, Ł.; Zabrocki, J.; Nachman, R.J. Solid-Phase Synthesis of an Insect Pyrokinin Analog Incorporating an Imidazoline Ring as Isosteric Replacement of a Trans Peptide Bond. Molecules 2021, 26, 3271, doi:10.3390/molecules26113271.
Kaczmarek, K.; Pacholczyk-Sienicka, B.; Albrecht, Ł.; Zabrocki, J.; Nachman, R.J. Solid-Phase Synthesis of an Insect Pyrokinin Analog Incorporating an Imidazoline Ring as Isosteric Replacement of a Trans Peptide Bond. Molecules 2021, 26, 3271, doi:10.3390/molecules26113271.
Abstract
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).
Keywords
insect neuropeptides; pyrokinins; trans peptide bond; imidazoline ring; SPOS;
Subject
Chemistry and Materials Science, Medicinal Chemistry
Copyright:
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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