Structural characterisation of trimethylsilyl-protected DNA bases

Gabriele Kociok-Kohn, Kieran C. Molloy, Gareth J. Price, Douglas R.G. Smith

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The structures of the silylated DNA bases, bis(trimethylsilyl)thymine (1), bis(trimethylsilyl)cytosine (2), bis(trimethylsilyl)adenine (3) and tris(trimethylsilyl)guanine (4), have been determined. 1 is O-silylated and displays no intermolecular interactions. 2 is silylated at both exocylic O, N positions and forms a chain structure through intermolecular NH⋯O and NH⋯N hydrogen bonds. 3 contains two SiMe3 groups, on the exocylic NH and endocyclic N9 position, respectively; of two independent molecules in the asymmetric unit, one dimerises through complementary NH⋯N hydrogen bonds, while the other forms a strained intramolecular hydrogen bond through the same pair of donor and acceptor centres. 4 incorporates N, N, O-SiMe3 moieties and forms chains via bifurcated CH⋯O/N hydrogen bonds, while the NH function remains unexploited. The effects of silylation on these pyrimidine and purine ring structures are also discussed in comparison with the native bases.

Original languageEnglish
Pages (from-to)697-707
Number of pages11
JournalSupramolecular Chemistry
Volume20
Issue number8
Early online date19 Nov 2008
DOIs
Publication statusPublished - Dec 2008

Keywords

  • Adenine
  • Cytosine
  • Guanine
  • Silylated DNA bases, thymine
  • X-ray structure determinations

ASJC Scopus subject areas

  • Chemistry(all)

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