Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2007, Issue 4, Pages 681-688Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200600747
Keywords
peptide nucleic acids; solid-phase synthesis; flavin; oxetane; electron transfer
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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. (C) Wiley-VCH Verlag GmbH & Co.
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