Size- and Structure-Selective Noncovalent Recognition of Saccharides by Tetraethyl and Tetraphenyl Resorcinarenes in the Gas Phase

Research output: Contribution to journalArticleScientificpeer-review

Researchers

  • Elina Kalenius
  • Timo Kekäläinen
  • Raisa Neitola
  • Ngong Kodiah Beyeh
  • Kari Rissanen
  • Pirjo Vainiotalo

Research units

  • University of Joensuu
  • University of Jyväskylä

Abstract

The noncovalent complexation of tetraethyl and tetraphenyl resorcinarenes with mono-, di-, and oligosaccharides was studied with negative-polarization electrospray ionization quadrupole ion trap and electrospray ionization Fourier-transform ion cyclotron resonance mass-spectrometric analysis. The saccharides formed 1:1 complexes with deprotonated resorcinarenes, which exhibited clear size and structure selectivity in their complexation. In the case of the monosaccharides, hexoses formed much more abundant and kinetically stable complexes than pentoses or deoxyhexoses. A comparison of the mono-, di-, and oligosaccharides revealed that both the relative abundance and stability of the complexes increase up to biose and triose, but start to decrease after that point, as the length of the oligosaccharide is increased. This behavior was rationalized by comparing the lowest-energy conformations of the complexes formed between the resorcinarene and oligosaccharides. This comparison was achieved by using theoretical calculations and X-ray crystal studies.

Details

Original languageEnglish
Pages (from-to)5220–5228
JournalCHEMISTRY: A EUROPEAN JOURNAL
Volume14
Issue number17
Publication statusPublished - Jun 2008
MoE publication typeA1 Journal article-refereed

ID: 11468509