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Molecules 2014, 19(3), 3135-3148;

Synthesis of PNA Oligoether Conjugates

Department of Biosciences and Nutrition, Karolinska Institutet, Novum, Hälsovägen Huddinge 7, 14183, Sweden
ICL-IP Terneuzen, Frankrijkweg BJ, Terneuzen 6 4538, The Netherlands
Department of Chemistry, University of Turku, Turku 20014, Finland
Author to whom correspondence should be addressed.
Received: 21 January 2014 / Revised: 1 March 2014 / Accepted: 4 March 2014 / Published: 13 March 2014
(This article belongs to the Special Issue Bioconjugations)
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Several different approaches have been explored for conjugation of oligoethers to PNA with internally or N-terminal placed diaminopropionic acid residues. Single and double conjugation of 2-(2-(2-aminoethoxy)ethoxy)ethanol was obtained using carbonyldimidazole. Using a post PNA-assembly coupling procedure the building block 2-(2-(2-(benzoyloxy)ethoxy)ethoxy)acetic acid multiple attachment of 2-(2-(2-hydroxyethoxy)ethoxy)acetyl groups to both N-terminal and β-amino groups of inserted diaminopropionic acids residues was achieved. Use of a new oligoether functionalized amino acid allows inclusion of oligoether conjugates during on-line machine assisted synthesis which also allowed combination of methods for attachment of different oligoethers and co-conjugation of neocuproine as well as conjugation of an aminosugar. View Full-Text
Keywords: peptide nucleic acid; polyethyleneglycol; aminosugar; neocuproine peptide nucleic acid; polyethyleneglycol; aminosugar; neocuproine

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Ghidini, A.; Steunenberg, P.; Murtola, M.; Strömberg, R. Synthesis of PNA Oligoether Conjugates. Molecules 2014, 19, 3135-3148.

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