Short and Efficient Synthesis of Alkyne‐Modified Amino Glycoside Building Blocks

Abstract

AbstractIn the light of recent progress in RNA biology, the need for molecules that bind to RNA and thus may be suited to manipulating RNA‐mediated processes is steadily increasing. We present a very short and efficient synthetic route to alkyne‐modified neamine and 2‐deoxystreptamine derivatives on a half‐gram scale. These derivatives are suitable for constructing a library of potential divalent RNA binders by copper‐catalysed 1,3‐dipolar cycloaddition to diazides (“click chemistry”). The conjugate dimers thus formed inhibitedDicer‐mediated micro‐RNA maturation with IC50 values between 0.6 and 15 μM.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)