Premium
Solid‐Phase Synthesis of Acid‐Sensitive N ‐(2‐Aminoethyl)glycine‐PNA Oligomers by the Fmoc/Bhoc Strategy
Author(s) -
Stafforst Thorsten,
Diederichsen Ulf
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600747
Subject(s) - chemistry , oxetane , moiety , oligomer , glycine , solid phase synthesis , nucleic acid , combinatorial chemistry , stereochemistry , polymer chemistry , amino acid , peptide , biochemistry
In 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)