School of Chemistry, The University of Sydney, 2006 NSW, Australia.
Org Lett. 2010 Jul 16;12(14):3136-9. doi: 10.1021/ol101018w.
Cyclic tetrapeptides have generated great interest because of their broad-ranging biological properties. In order to synthesize these highly strained 12-membered cyclic compounds, a cyclization strategy using pseudoprolines as removable turn inducers has been developed. The pseudoproline derivatives induce a cisoid amide bond in the linear peptide backbone which facilitates cyclization. After cyclization, the turn inducers can be readily removed to afford cyclic tetrapeptides containing serine or threonine residues.
由于具有广泛的生物学特性，环状四肽引起了极大的兴趣。为了合成这些高度应变的 12 元环化合物，开发了一种使用伪脯氨酸作为可去除的环化诱导物的环化策略。伪脯氨酸衍生物在直链肽骨架中诱导顺式酰胺键，从而有利于环化。环化后，可轻易去除环化诱导物，得到含有丝氨酸或苏氨酸残基的环状四肽。
