Gharakhanian Eric G, Deming Timothy J
Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095, USA.
Chem Commun (Camb). 2016 Apr 18;52(30):5336-9. doi: 10.1039/c6cc01253a. Epub 2016 Mar 23.
A methodology was developed for efficient, chemoselective transformation of methionine residues into stable, functional homocysteine derivatives. Methionine residues can undergo highly chemoselective alkylation reactions at low pH to yield stable sulfonium ions, which could then be selectively demethylated to give stable alkyl homocysteine residues. This mild, two-step process is chemoselective, efficient, tolerates many functional groups, and provides a means for creation of new functional biopolymers, site-specific peptide tagging, and synthesis of biomimetic and structural analogs of peptides.
已开发出一种方法，可将甲硫氨酸残基高效、化学选择性地转化为稳定的、功能性高半胱氨酸衍生物。甲硫氨酸残基在低pH值下可发生高度化学选择性的烷基化反应，生成稳定的锍离子，然后可将其选择性脱甲基，得到稳定的烷基高半胱氨酸残基。这种温和的两步法具有化学选择性、高效，能耐受许多官能团，并为新型功能性生物聚合物的制备、位点特异性肽标记以及肽的仿生和结构类似物的合成提供了一种手段。
