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- Title
Hydrophilic modifications in peptide nucleic acid — Synthesis and properties of PNA possessing 5-hydroxymethyluracil and 5-hydroxymethylcytosine.
- Authors
Yuhong Liu; Filip Wojciechowski; Hudson, Robert H. E.
- Abstract
We have investigated the chemistry for the incorporation of C5-hydroxymethyl-uracil and -cytosine in peptide nucleic acid (PNA) and the subsequent effect of this modification on PNA hybridization behavior. Largely based on literature precedent, we prepared a peptide nucleic acid monomer, possessing 5-hydroxymethyuracil, which was compatible with Fmoc-based oligopeptide synthesis. An improved, large-scale synthesis of 5-hydroxymethylcytosine was developed, as a starting point for the synthesis of a monomer containing this nucleobase. In each case, the hydroxyl group was blocked as a t-butyldiphenylsilyl ether, and the exocyclic amino group of cytosine was additionally blocked with the benzoyl-group. The modified monomers were incorporated into isolated positions in the oligomer sequence using standard protocols. The modified oligomers showed that the 5-hydroxymethyl group is compatible with triplex and duplex formation.Key words: peptide nucleic acid, hydroxymethyluracil, hydroxymethylcytosine, modified nucleobase, hybridization.
- Subjects
NUCLEIC acids; NUCLEIC acid hybridization; MONOMERS; OLIGOMERS; ENZYMES
- Publication
Canadian Journal of Chemistry, 2007, Vol 85, Issue 4, p302
- ISSN
0008-4042
- Publication type
Article
- DOI
10.1139/V07-030