Sun Haizhou, Martin Connor, Kesselring David, Keller Rebecca, Moeller Kevin D
Department of Chemistry, Washington University, St. Louis, Missouri 63130, USA.
J Am Chem Soc. 2006 Oct 25;128(42):13761-71. doi: 10.1021/ja064737l.
A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.
一系列硅烷基取代的氨基酸已被合成，插入到肽中，然后用作氧化生成反应性N-酰基亚胺离子的前体。电化学和化学氧化程序均已采用。已证明在固相底物中生成N-酰基亚胺离子以及将其应用于一个官能化二肽的小文库。定义了硅烷基的富电子程度以及较长肽中多个硅烷基的兼容性方面的限制。
