Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
Org Biomol Chem. 2011 Feb 7;9(3):676-8. doi: 10.1039/c0ob00795a. Epub 2010 Dec 3.
Aminoacyl phosphate monoesters can be prepared free of an amino-protecting group and used directly in lanthanum-promoted selective monoacylation of either the 2' or 3'-hydroxyl of nucleosides and nucleotides. For example, phenylalanyl ethyl phosphate rapidly forms esters with either of the 2' or 3'-hydroxyls of ribonucleosides and nucleotides in the presence of lanthanum ions in aqueous buffer. Oligomerization of the aminoacyl phosphate is much slower than ester formation and is not a competitive process. Competing hydrolysis of the reagent is slow. By extension, this route should provide a simplified general route to synthetically aminoacylated derivatives of tRNA.
氨酰磷酸单酯可以在没有氨基保护基团的情况下制备，并直接用于镧促进的核苷和核苷酸的 2'或 3'-羟基选择性单酰化。例如，苯丙氨酰乙基磷酸酯在水缓冲液中存在镧离子时，迅速与核糖核苷和核苷酸的 2'或 3'-羟基形成酯。氨酰磷酸的聚合比酯的形成慢得多，并且不是一个竞争过程。试剂的竞争性水解很慢。由此推断，这条路线应该为 tRNA 的合成氨酰化衍生物提供一种简化的通用途径。
