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Synthesis of 3-aminolactams as X-Gly constrained pseudodipeptides and conformational study of a Trp-Gly surrogate

By Marta Ecija, Anna Diez, Mario Rubiralta, Nuria Casmitjana, Marcelo Kogan Bocian and Ernest Giralt

Abstract

Artículo de publicación ISI3-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} pseudo-dipeptides. Conformational analyses of tripeptide analogues Ac-{Trp-Gly}-Leu-NH2 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

Topics: DIELS-ALDER REACTIONS
Publisher: AMER CHEMICAL SOC
Year: 2003
DOI identifier: 10.1021/jo035151+
OAI identifier: oai:repositorio.uchile.cl:2250/121499
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