The Chair of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Ljubljana, Aškerčeva 7, 1000 Ljubljana, Slovenia.
Molecules. 2019 Apr 1;24(7):1261. doi: 10.3390/molecules24071261.
Despite the great importance of β-lactam antibiotics, there is still a limited number of synthetic approaches for the formation of β-lactam⁻containing dipeptides. In this study, we report upon the stereoselective preparation of β-lactam⁻containing pseudopeptides, where different reaction conditions and NH₂ protective groups were tested to obtain compounds that contain 3-amino-azetidin-2-one. We demonstrate that the protective group is essential for the outcome of the reaction. Successful implementation of dibenzyl-protected serine-containing dipeptides through the Mitsunobu reaction can provide the desired products at high yields and stereoselectivity.
尽管β-内酰胺抗生素非常重要，但形成含β-内酰胺的二肽的合成方法仍然有限。在这项研究中，我们报告了立体选择性制备含β-内酰胺的假肽，其中测试了不同的反应条件和 NH2 保护基，以获得含有 3-氨基-氮杂环丁-2-酮的化合物。我们证明保护基对于反应的结果是必不可少的。通过 Mitsunobu 反应成功实施二苄基保护的丝氨酸二肽可以以高产率和立体选择性提供所需产物。
