Chiral discrimination of monosaccharides using a fluorescent molecular sensor

Tony D. James, K. R.A. Samankumara Sandanayake, Seiji Shinkai

Research output: Contribution to journalArticle

529 Citations (Scopus)

Abstract

MEANS of distinguishing between enantiomers of a chiral molecule are of critical importance in many areas of analytical chemistry and biotechnology, particularly in drug design and synthesis. In particular, solution-based sensor systems capable of chiral recognition would be of tremendous pharmaceutical value. Here we report the chiral discrimination of D- and L -monosaccharides using a designed receptor molecule that acts as a sensor by virtue of its fluorescent response to binding of the guest species. Our receptor contains boronic acid groups that bind saccharides by covalent interactions; such receptor systems have been much studied previously1−6 for complexation of saccharides, and have an advantage over others based on hydrogen-bonding interactions7−11, for which polar protic solvents such as water can compete with guest binding. Our molecular sensor also incorporates a fluorescent naphthyl moiety; binding of each enantiomer of the monosaccharides alters the fluorescence intensity to differing degrees, enabling them to be distinguished. These water-soluble molecular sensors might form the basis of a quantitative and selective analytical method for saccharides.

Original languageEnglish
Pages (from-to)345-347
Number of pages3
JournalNature
Volume374
Issue number6520
DOIs
Publication statusPublished - Mar 23 1995
Externally publishedYes

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Monosaccharides
Enantiomers
Sensors
Boronic Acids
Molecules
Water
Biotechnology
Complexation
Pharmaceutical Preparations
Hydrogen bonds
Fluorescence
Chemical analysis

All Science Journal Classification (ASJC) codes

  • General

Cite this

James, T. D., Samankumara Sandanayake, K. R. A., & Shinkai, S. (1995). Chiral discrimination of monosaccharides using a fluorescent molecular sensor. Nature, 374(6520), 345-347. https://doi.org/10.1038/374345a0

Chiral discrimination of monosaccharides using a fluorescent molecular sensor. / James, Tony D.; Samankumara Sandanayake, K. R.A.; Shinkai, Seiji.

In: Nature, Vol. 374, No. 6520, 23.03.1995, p. 345-347.

Research output: Contribution to journalArticle

James, TD, Samankumara Sandanayake, KRA & Shinkai, S 1995, 'Chiral discrimination of monosaccharides using a fluorescent molecular sensor', Nature, vol. 374, no. 6520, pp. 345-347. https://doi.org/10.1038/374345a0
James TD, Samankumara Sandanayake KRA, Shinkai S. Chiral discrimination of monosaccharides using a fluorescent molecular sensor. Nature. 1995 Mar 23;374(6520):345-347. https://doi.org/10.1038/374345a0
James, Tony D. ; Samankumara Sandanayake, K. R.A. ; Shinkai, Seiji. / Chiral discrimination of monosaccharides using a fluorescent molecular sensor. In: Nature. 1995 ; Vol. 374, No. 6520. pp. 345-347.
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