caa a22 4500 445326638 CHVBK 20180317142723.0 cr unu---uuuuu 170323e20110601xx s 000 0 eng 10.1007/s10989-011-9246-z doi (NATIONALLICENCE)springer-10.1007/s10989-011-9246-z On the Manner of Cyclization of N -Acylated Aspartic and Glutamic Acid Derivatives [Elektronische Daten] [Paweł Zajdel, Christine Enjalbal, Marek Żylewski, Gilles Subra] When synthesizing arylpiperazine library modified with N-acylated amino acid derivatives (e.g., cyclized aspartic acid, cyclized glutamic acid, proline) we wished to rapidly determine the way of cyclization of N-acylated glutamic acid derivatives. During concomitant cleavage and cyclization two alternative routes were possible—either formation of six-member imide (glutarimide) or five-member lactam. Application of MS/MS and 1H NMR method allowed us to establish that cyclization of N-acylated glutamic acid derivatives preceded to lactams—N-acylated pyroglutamic acid derivatives. Graphical Abstract: Under acidic treatment the Lantern bound N-acylated glutamic acid derivatives underwent concomitant cleavage and cyclization. Herein, we studied two alternative cyclization routes—imides, lactams. It was found that cyclization of N-acylated glutamic acid derivatives yielded pyroglutamic acid derivatives (Structure C). Springer Science+Business Media, LLC, 2011 Solid-phase synthesis nationallicence Aspartic acid cyclization nationallicence Glutamic acid cyclization nationallicence Pyroglutamic acid nationallicence Mass spectrometry nationallicence SynPhase Lanterns nationallicence Zajdel Paweł Department of Medicinal Chemistry, Jagiellonian University Medical College, 9 Medyczna Street, 30-688, Kraków, Poland aut Enjalbal Christine Équipe Aminoacides Peptides et Protéines, Institut des Biomolécules Max Mousseron IBMM, UMR CNRS 5247, Faculté de Pharmacie, Université Montpellier I et II, 15 avenue Charles Flahault, 34060, Montpellier, France aut Żylewski Marek Department of Organic Chemistry, Jagiellonian University Medical College, 9 Medyczna Street, 30-688, Kraków, Poland aut Subra Gilles Équipe Aminoacides Peptides et Protéines, Institut des Biomolécules Max Mousseron IBMM, UMR CNRS 5247, Faculté de Pharmacie, Université Montpellier I et II, 15 avenue Charles Flahault, 34060, Montpellier, France aut International Journal of Peptide Research and Therapeutics Springer Netherlands 17/2(2011-06-01), 93-100 1573-3149 17:2<93 2011 17 10989 https://doi.org/10.1007/s10989-011-9246-z text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10989-011-9246-z text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Zajdel Paweł Department of Medicinal Chemistry, Jagiellonian University Medical College, 9 Medyczna Street, 30-688, Kraków, Poland aut NATIONALLICENCE 700 1- Enjalbal Christine Équipe Aminoacides Peptides et Protéines, Institut des Biomolécules Max Mousseron IBMM, UMR CNRS 5247, Faculté de Pharmacie, Université Montpellier I et II, 15 avenue Charles Flahault, 34060, Montpellier, France aut NATIONALLICENCE 700 1- Żylewski Marek Department of Organic Chemistry, Jagiellonian University Medical College, 9 Medyczna Street, 30-688, Kraków, Poland aut NATIONALLICENCE 700 1- Subra Gilles Équipe Aminoacides Peptides et Protéines, Institut des Biomolécules Max Mousseron IBMM, UMR CNRS 5247, Faculté de Pharmacie, Université Montpellier I et II, 15 avenue Charles Flahault, 34060, Montpellier, France aut NATIONALLICENCE 773 0- International Journal of Peptide Research and Therapeutics Springer Netherlands 17/2(2011-06-01), 93-100 1573-3149 17:2<93 2011 17 10989 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer