Solid Phase versus Solution Phase Synthesis ofHeterocyclic Macrocycles

Molecules

Seong Jong Kim¹ 

[1] School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia

关键词: urukthapelstatin A;    cytotoxic;    macrocycle;    peptides;    heterocycle;    thiazole;    oxazole;    telomestatin;    solid phase peptide synthesis;   

DOI  :  10.3390/molecules18011111

来源: mdpi

【 摘 要 】

Comparing a solution phase route to a solid phase route in the synthesis of the cytotoxic natural product urukthapelstatin A (Ustat A) confirmed that a solid phase method is superior. The solution phase approach was tedious and involved cyclization of a ridged heterocyclic precursor, while solid phase allowed the rapid generation of a flexible linear peptide. Cyclization of the linear peptide was facile and subsequent generation of three oxazoles located within the structure of Ustat A proved relatively straightforward. Given the ease with which the oxazole Ustat A precursor is formed via our solid phase approach, this route is amenable to rapid analog synthesis.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.