Macías Alberto, Ramallal Antonio Morán, Alonso Eduardo, del Pozo Carlos, González Javier
Departamento de Química Organica e Inorganica, Universidad de Oviedo, Julian Clavería 8, 33006 Oviedo, Spain.
J Org Chem. 2006 Sep 29;71(20):7721-30. doi: 10.1021/jo061189l.
The synthesis of the two enantiomers of pyrrolidine-derived spiro beta-lactams by resolution with D- and L-Boc phenylalanine is described. The potential of these optically active spiro beta-lactams on the synthesis of peptidomimetics as analogues of melanostatin is evaluated. Theoretical studies of several models, at the Becke3LYP/6-31+G* level of theory, together with previous experimental evidences from our group, gathered by NMR, allow us to design structures that can efficiently mimic some biologically active peptide-type molecules. On the other hand, the spiro beta-lactams have shown their utility in the preparation of beta-peptides. As an example, a homo-tetra-beta-peptide was synthesized. This research will continue in the future in order to obtain higher peptides with potential biological activity.
描述了通过用D-和L-Boc苯丙氨酸拆分来合成吡咯烷衍生的螺环β-内酰胺的两种对映体。评估了这些光学活性螺环β-内酰胺在合成作为黑素抑制素类似物的拟肽方面的潜力。在Becke3LYP/6-31+G*理论水平上对几种模型进行的理论研究，以及我们小组以前通过核磁共振收集的实验证据，使我们能够设计出可以有效模拟一些生物活性肽型分子的结构。另一方面，螺环β-内酰胺已显示出它们在制备β-肽方面的效用。例如，合成了一种同型四-β-肽。未来将继续这项研究，以获得具有潜在生物活性的更高肽段。
