1034473-19-2Relevant articles and documents
Rapid generation of macrocycles with natural-product-like side chains by multiple multicomponent macrocyclizations (MiBs)
Rivera, Daniel G.,Vercillo, Otilie E.,Wessjohann, Ludger A.
experimental part, p. 1787 - 1795 (2008/10/09)
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 α-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. The Royal Society of Chemistry.
