Synthesis of 3-aminolactams as X-Gly constrained pseudodipeptides and conformational study of a Trp-Gly surrogate |
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| Authors: | Ecija Marta Diez Anna Rubiralta Mario Casamitjana Núria Kogan Marcelo J Giralt Ernest |
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| Institution: | Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain, and Parc Científic de Barcelona, c/ Josep Samitier, 1-5, 08028-Barcelona, Spain. |
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| Abstract: | 3-Amino-delta-valerolactams trans-11a-c were synthesized through conjugate addition and Curtius rearrangement and converted into Fmoc-Trp-Gly], Fmoc-Ile-Gly], and Fmoc-Phe-Gly] pseudodipeptides. Conformational analyses of tripeptide analogues Ac-Trp-Gly]-Leu-NH(2) 17a and 17b by NMR experiments and molecular modeling calculations showed that diastereomer 17a adopted a gamma-turn/distorted type II beta-turn structure, whereas diastereomer 17b adopted mainly a gamma-turn structure. |
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