Fmoc/Acyl protecting groups in the synthesis of polyamide (peptide) nucleic acid monomers

Zoltán Timár, L. Kovács, Györgyi Kovács, Zoltán Schmél

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The chemical synthesis of polyamide (peptide) nucleic acid (PNA) monomers 22-25 has been accomplished using Fmoc [N-(2-aminoethyl)glycine backbone], anisoyl (adenine), 4-tert-butylbenzoyl (cytosine) and isobutyryl/ diphenylcarbamoyl (guanine) protecting-group combinations, thus allowing oligomer synthesis on both peptide and oligonucleotide synthesizers. An alternative method for the preparation of (N6-anisoyladenin-9-yl)acetic acid 7 is described using partial hydrolysis of a dianisoylated derivative. Different methods were studied for guanine alkylation including (a) Mitsunobu reaction; (b) low-temperature, sodium hydride- and (c) N,N-diisopropylethylaminemediated alkylation reactions to give preferentially N9-substituted derivatives. Empirical rules are proposed for differentiating N 9/N7-substituted guanines based on their 13C NMR chemical-shift differences.

Original languageEnglish
Pages (from-to)19-26
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number1
Publication statusPublished - 2001

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Peptide Nucleic Acids
Nylons
Guanine
Monomers
Alkylation
Derivatives
Cytosine
Chemical shift
Adenine
Oligomers
Oligonucleotides
Acetic Acid
Hydrolysis
Nuclear magnetic resonance
Peptides
Temperature

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Fmoc/Acyl protecting groups in the synthesis of polyamide (peptide) nucleic acid monomers. / Timár, Zoltán; Kovács, L.; Kovács, Györgyi; Schmél, Zoltán.

In: Journal of the Chemical Society, Perkin Transactions 1, No. 1, 2001, p. 19-26.

Research output: Contribution to journalArticle

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