PNA-Directed Triple-Helix Formation by N7-Xanthine

PNA-Directed Triple-Helix Formation by N7-Xanthine

Abstract We report the first example of alkylation of underivatized xanthine with chloroacetic acid to yield a separable mixture of N 7 - and N 9 -(methylenecarboxyl)xanthine and its conversion to a peptide nucleic acid monomer compatible with Fmoc-based oligomerization chemistry. Additionally, we h...

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Veröffentlicht in:Synlett 2005-06, Vol.2005 (9), p.1442-1446
Hauptverfasser: Hudson, Robert H., Goncharenko, Mykhaylo, Wallman, Andrew P., Wojciechowski, Filip
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container_issue 9
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container_title Synlett
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creator Hudson, Robert H.
Goncharenko, Mykhaylo
Wallman, Andrew P.
Wojciechowski, Filip
description Abstract We report the first example of alkylation of underivatized xanthine with chloroacetic acid to yield a separable mixture of N 7 - and N 9 -(methylenecarboxyl)xanthine and its conversion to a peptide nucleic acid monomer compatible with Fmoc-based oligomerization chemistry. Additionally, we have simultaneously prepared the N 7 - and N 9 -PNA monomers of guanine by alkylation of 2-N-isobutyrylguanine which were subsequently separated. Molecular modeling of the nucleobase base triplets indicates that N 7 -xanthine and N 7 -guanine form isomorphous triplets with adenine and guanine, respectively. We also show that polyamides containing N 7 -xanthine are compatible with triple-helix formation.
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title PNA-Directed Triple-Helix Formation by N7-Xanthine
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