Issue 3, 2011

Biomimetic protecting-group-free 2′, 3′-selective aminoacylation of nucleosides and nucleotides

Abstract

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.

Graphical abstract: Biomimetic protecting-group-free 2′, 3′-selective aminoacylation of nucleosides and nucleotides

Supplementary files

Article information

Article type
Communication
Submitted
28 Sep 2010
Accepted
18 Nov 2010
First published
19 Nov 2010

Org. Biomol. Chem., 2011,9, 676-678

Biomimetic protecting-group-free 2′, 3′-selective aminoacylation of nucleosides and nucleotides

S. Her and R. Kluger, Org. Biomol. Chem., 2011, 9, 676 DOI: 10.1039/C0OB00795A

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