化学
拟肽
位阻效应
光延反应
内酰胺
酰化
戒指(化学)
丝氨酸
组合化学
立体化学
有机化学
催化作用
肽
生物化学
酶
作者
Robert L. Broadrup,Bei Wang,William P. Malachowski
出处
期刊:Tetrahedron
[Elsevier]
日期:2005-10-01
卷期号:61 (43): 10277-10284
被引量:21
标识
DOI:10.1016/j.tet.2005.08.029
摘要
A selection of azapeptidomimetics containing constraining lactam rings have been prepared by Mitsunobu cyclization of serine/homologated serine-azaalanine derivatives. These include sterically-congested β-lactams, as well as γ-butyrolactam and δ-valerolactam analogs. A novel azaamino acid acylation method was developed to prepare the sterically demanding α-benzyl-serine-azaalanine precursor. In all cases, the Mitsunobu conditions were highly efficient in forming the desired azapeptidomimetic lactams. The reported process represents a general strategy for the synthesis of peptidomimetic structures with a constraining lactam ring.
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