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Issue 14, 2008

O-Allyl protection in the Fmoc-based synthesis of difficult PNA

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Abstract

The synthesis of homothymine PNA-oligomers can be plagued by the occurrence of a significant amount of truncation products, probably because on-resin aggregation hinders access during the coupling reactions. The use of low resin loading and the addition of the chaotropic salt KSCN in DMF allowed a partial remedy by conferring enhancements to the coupling yields. However, protection of the imide group by using O-allyl-protected thymine Fmoc-tAll provided the most significant improvements to the yields, even in cases where the use of non-protected thymine building blocks resulted in 70% truncation products. Deallylation occurs during the TFA cleavage step. Thus, O-allyl-protection can be applied in combination with standard protocols used in automated PNA synthesis.

Graphical abstract: O-Allyl protection in the Fmoc-based synthesis of difficult PNA

Article information


Submitted
27 Mar 2008
Accepted
31 Mar 2008
First published
15 May 2008

Org. Biomol. Chem., 2008,6, 2493-2498
Article type
Paper

O-Allyl protection in the Fmoc-based synthesis of difficult PNA

F. Altenbrunn and O. Seitz, Org. Biomol. Chem., 2008, 6, 2493 DOI: 10.1039/B805165H

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