Ten Brink Hefziba T, Meijer Joris T, Geel Remon V, Damen Mark, Löwik Dennis W P M, van Hest Jan C M
Organic Chemistry Department, IMM Institute, Radboud University Nijmegen, Toernooiveld 1, 6525 ED, Nijmegen, The Netherlands.
J Pept Sci. 2006 Nov;12(11):686-92. doi: 10.1002/psc.780.
In this paper, a straightforward and generic protocol is presented to label the C-terminus of a peptide with any desired moiety that is functionalized with a primary amine. Amine-functional molecules included are polymers (useful for hybrid polymers), long alkyl chains (used in peptide amphiphiles and stabilization of peptides), propargyl amine and azido propyl-amine (desirable for 'click' chemistry), dansyl amine (fluorescent labeling of peptides) and crown ethers (peptide switches/hybrids). In the first part of the procedure, the primary amine is attached to an aldehyde-functional resin via reductive amination. To the secondary amine that is produced, an amino acid sequence is coupled via a standard solid-phase peptide synthesis protocol. Since one procedure can be applied for any given amine-functional moiety, a robust method for C-terminal peptide labeling is obtained.
本文提出了一种直接且通用的方案，用于用任何带有伯胺官能团的所需部分标记肽的C末端。所包含的胺官能分子有聚合物（对杂化聚合物有用）、长烷基链（用于肽两亲物和肽的稳定化）、炔丙胺和叠氮丙胺（适用于“点击”化学）、丹磺酰胺（用于肽的荧光标记）和冠醚（肽开关/杂化物）。在该过程的第一部分，通过还原胺化将伯胺连接到醛官能树脂上。对于生成的仲胺，通过标准的固相肽合成方案偶联氨基酸序列。由于一种方案可应用于任何给定的胺官能部分，因此获得了一种可靠的C末端肽标记方法。
