Boronic acid-based bipyridinium salts as tunable receptors for monosaccharides and alpha-hydroxycarboxylates.
Several novel diboronic acid-substituted bipyridinium salts were prepared and, using a fluorescent reporter dye, were tested for their ability to selectively bind various monosaccharides and alpha-hydroxycarboxylates in an aqueous medium. The fluorescence sensing mechanism relies on the formation of a ground-state charge-transfer complex between the dye and bipyridinium. An X-ray crystal structure of this complex is described herein. Glucose selectivity over fructose and galactose was achieved by designing the bipyridinium-based receptors to be capable of attaining a 1:1 receptor/substrate stoichiometry via cooperative diboronic acid binding.
Gamsey
Soya
S
Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, USA.
Miller
Aaron
A
Olmstead
Marilyn M
MM
Beavers
Christine M
CM
Hirayama
Lacie C
LC
Pradhan
Sulolit
S
Wessling
Ritchie A
RA
Singaram
Bakthan
B
D015374:Biosensing Techniques / Q000379:methods*; D001897:Boronic Acids / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000737:chemistry; D005632:Fructose / Q000737:chemistry; D005690:Galactose / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D009005:Monosaccharides / Q000737:chemistry*; D011726:Pyridinium Compounds / Q000737:chemistry*; D012492:Salts / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D014867:Water / Q000737:chemistry
D001897:Boronic Acids; D002264:Carboxylic Acids; D005456:Fluorescent Dyes; D009005:Monosaccharides; D011726:Pyridinium Compounds; D012492:Salts; D014867:Water; D005632:Fructose; D005947:Glucose; D005690:Galactose