Solid‐Phase Synthesis of Acid‐Sensitive N‐(2‐Aminoethyl)glycine‐PNA Oligomers by the Fmoc/Bhoc Strategy

Abstract

AbstractIn the context of investigation of nucleic acid‐mediated excess electron transfer, a bis‐functionalized (2‐aminoethyl)glycine‐PNA modified with a flavin and an oxetane moiety was synthesized. The solid‐phase synthesis of the required PNA oligomer was especially intriguing because of the high acid sensitivity of the oxetane moiety, so the Fmoc/Bhoc strategy was adapted to the mild cleavage conditions of the Sieberamide resin. Along with smooth oligomerization conditions, the syntheses of oxetane‐ and flavin‐functionalized Fmoc‐protected (2‐aminoethyl)glycine building blocks are reported. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)