Molecular design of boronic acid-based dye receptors for nucleosides

Masayuki Takeuchi, Masahiro Taguchi, Hideyuki Shinmori, Seiji Shinkai

Research output: Contribution to journalArticlepeer-review

43 Citations (Scopus)


Chromophric receptors for nucleosides were designed utilizing the boronic acid-diol interaction which effectively operates in aqueous solution. Receptors consist of a boronic acid moiety and a dimethylaminophenylazo moiety. The boronic acid moiety forms a covalently-bonded ester linkage with the 2,3-diol group in nucleosides in a reversible manner and the anionic charge generated on the boron atom is stabilized intramolecularly by the pyridinium cation. The azo moiety can overlap with the heteroaromatic ring moiety in nucleosides to stabilize the complex. The complexation constants could be conveniently determined by the absorption spectral change. Comparison of the complexation constants with those of 2-deoxyadenosine without 2-OH and 1,4-anhydroerythritol without the heteroaromatic ring established that the complex formation is primarily due to the boronic acid-diol (2,3-diol) interaction and secondarily facilitated by the hydrophobic and/or π-π stacking interactions.

Original languageEnglish
Pages (from-to)2613-2618
Number of pages6
JournalBulletin of the Chemical Society of Japan
Issue number9
Publication statusPublished - Sept 1996
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • General Chemistry


Dive into the research topics of 'Molecular design of boronic acid-based dye receptors for nucleosides'. Together they form a unique fingerprint.

Cite this