Rivera Daniel G, Vercillo Otilie E, Wessjohann Ludger A
Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120, Halle/Saale, Germany.
Org Biomol Chem. 2008 May 21;6(10):1787-95. doi: 10.1039/b715393g. Epub 2008 Mar 28.
A small parallel library of peptoid macrocycles with natural-product-derived side chains of biological importance was produced by Ugi-type multiple multicomponent macrocyclizations including bifunctional building blocks (Ugi-MiBs). Diverse exocyclic elements of high relevance in natural recognition processes, i.e., all functional amino acid residues (e.g., Cys, Arg, His, Trp) and even sugar moieties, can be introduced in a one-pot process into different types of peptoid-containing macrocyclic skeletons. This is exemplified by the use of a diamine/diisocyanide combination of Ugi-MiBs and N-protected alpha-amino acids or carboxy-functionalized carbohydrates as source for the natural-product-like exocyclic elements. Employed as the acid components of the multiple Ugi reactions, they appear as N-amide substituents on the macrocyclic cores. The use of different diamines and diisocyanides allows an easy variation of the N- to C-directionality and therefore of the position of the exocyclic elements.
通过包括双功能构件（Ugi-MiBs）的Ugi型多组分大环化反应，构建了一个小型的类肽大环平行文库，其侧链源自具有生物学重要性的天然产物。在天然识别过程中具有高度相关性的各种外环元素，即所有功能性氨基酸残基（如半胱氨酸、精氨酸、组氨酸、色氨酸）甚至糖部分，都可以通过一锅法引入到不同类型的含类肽大环骨架中。以使用Ugi-MiBs的二胺/二异氰化物组合以及N-保护的α-氨基酸或羧基官能化碳水化合物作为类天然产物外环元素的来源为例。它们作为多个Ugi反应的酸组分，以大环核心上的N-酰胺取代基形式出现。使用不同的二胺和二异氰化物可以轻松改变N到C的方向性，从而改变外环元素的位置。
