Kaniraj Prathap Jeya, Maayan G
Schulich Faculty of Chemistry, Technion - Israel Institute of Technology, Haifa, 32000, Israel.
Org Lett. 2015 May 1;17(9):2110-3. doi: 10.1021/acs.orglett.5b00696. Epub 2015 Apr 13.
We describe a fast and efficient side chain-to-tail cyclization of N-substituted glycine oligomers, peptoids, on a solid support and under microwave irradiation. We demonstrate that cyclic peptoids varied in their ring size and side chains can be synthesized by a bond formation between a chloropropyl group placed anywhere along the sequence and the secondary amine at the N-terminus. This SN2 reaction leads to the formation of a new C-N bond using only one reagent (a base).
我们描述了一种在固体支持物上并在微波辐射下，对N-取代甘氨酸低聚物（类肽）进行快速高效的侧链到尾环化反应。我们证明，通过沿着序列任意位置放置的氯丙基与N端的仲胺之间形成键，可以合成环大小和侧链各异的环肽。这种SN2反应仅使用一种试剂（碱）即可形成新的C-N键。
