Department of Chemistry, Harvard University, Cambridge, Massachusetts 02138, USA.
Org Lett. 2010 Jul 2;12(13):3046-9. doi: 10.1021/ol1010449.
The introduction of all-hydrocarbon i,i+3 staples into alpha-helical peptide scaffolds via ring-closing olefin metathesis (RCM) between two alpha-methyl,alpha-pentenylglycine residues incorporated at i and i+3 positions, which lie on the same face of the helix, has been investigated. The reactions were found to be highly dependent upon the side-chain stereochemistry of the amino acids undergoing RCM. The i,i+3 stapling system established here provides a potentially useful alternative to the well-established i,i+4 stapling system now in widespread use.
通过在位于同一螺旋面的 i 位和 i+3 位的两个α-甲基、α-戊烯基甘氨酸残基之间进行闭环烯烃复分解（RCM），将全碳氢 i,i+3 键引入α-螺旋肽支架中。反应高度依赖于经历 RCM 的氨基酸的侧链立体化学。此处建立的 i,i+3 键合系统为目前广泛使用的成熟的 i,i+4 键合系统提供了一种潜在的有用替代方案。
