Synthesis of 3-aminolactams as X-Gly constrained pseudodipeptides and conformational study of a Trp-Gly surrogate.
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.
Ecija
Marta
M
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.
Diez
Anna
A
Rubiralta
Mario
M
Casamitjana
Núria
N
Kogan
Marcelo J
MJ
Giralt
Ernest
E
D000588:Amines / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis*; D007769:Lactams / Q000138:chemical synthesis*; D007930:Leucine / Q000737:chemistry; D008956:Models, Chemical; D008968:Molecular Conformation; D009842:Oligopeptides / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D004151:Dipeptides; D007769:Lactams; D009842:Oligopeptides; C016810:tryptophylglycine; D007930:Leucine