Superiority of secondary hydroxy side modification in cyclodextrin complexation for hghly hydrophilic adenine nucleotides

Iwao Suzuki, Taku Miura, Jun Ichi Anzai

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Monoamino derivatives of β-cyclodextrin (β-CD) having an amino group either at the primary (1) or secondary hydroxy group side (2) were employed for investigating the superiority of the secondary hydroxy side modification to the guest binding of adenine nucleotides. Both 1 and 2 could form more stable host-guest complexes with AMP, ADP, and ATP than β-CD due to the electrostatic interaction between the ammonium group of the hosts and the phosphate groups of the guests. The effectiveness of the electrostatic interaction was supported by destabilization exerted by the presence of Mg2+. The guest binding constants of 2 for AMP, ADP, and ATP were 79, 140, and 160 dm3 mol-1, respectively, the values being larger than those of 1 by a factor of ∼2. On the other hand, comparable binding abilities between 1 and 2 were observed for adenosine incapable of interacting with a cationic ammonium group. These results demonstrate that 2 is a better host for the adenine nucleotides than 1, and, combining our previous results on crown ether-modified β-CDs, indicate the superiority of the secondary hydroxy side modification upon molecular recognition for hydrophilic guest compounds by CDs.

Original languageEnglish
Pages (from-to)283-288
Number of pages6
JournalJournal of Supramolecular Chemistry
Volume1
Issue number4-6
DOIs
Publication statusPublished - 2001 Jan 1

Keywords

  • Amino-cyclodextrin
  • Electrostatic interaction
  • Mg ion
  • Nucleotides
  • Secondary side modification

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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