Stereochemical and regiochemical trends in the selective detection of saccharides.
Several discreet sugar-boronate complexes exist in solution. This is due to the complex equilibria between isomeric species of even the simplest monosaccharides. In the current investigation, we determine the regio- and stereochemical features of the various equilibrating sugar isomers that induce signal transduction in boronic acid chemosensors such as 1 as well as 2 and 3. We present a unique example of a chemosensor (1) that is selective for ribose, adenosine, nucleotides, nucleosides, and congeners. As a result of this study, we are able to predict and achieve selective fluorescence and colorimetric responses to specific disaccharides as a consequence of their terminal sugar residue linkage patterns and configurations. We also find that the combined use of chemosensors exhibiting complementary reactivities may be used cooperatively to obtain enhanced selectivity for ribose and rare saccharides.
Jiang
Shan
S
Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, USA.
Escobedo
Jorge O
JO
Kim
Kyu Kwang
KK
Alptürk
Onur
O
Samoei
George K
GK
Fakayode
Sayo O
SO
Warner
Isiah M
IM
Rusin
Oleksandr
O
Strongin
Robert M
RM
D000241:Adenosine / Q000032:analysis / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D002236:Carbohydrate Conformation; D003124:Colorimetry; D005632:Fructose / Q000032:analysis / Q000737:chemistry; D005947:Glucose / Q000032:analysis / Q000737:chemistry; D008958:Models, Molecular; D009005:Monosaccharides / Q000032:analysis* / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D009705:Nucleosides / Q000032:analysis / Q000737:chemistry; D009711:Nucleotides / Q000032:analysis / Q000737:chemistry; D009844:Oligosaccharides / Q000032:analysis* / Q000737:chemistry; D012266:Ribose / Q000032:analysis / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D001897:Boronic Acids; D009005:Monosaccharides; D009705:Nucleosides; D009711:Nucleotides; D009844:Oligosaccharides; C003243:psicose; D005632:Fructose; C002055:allose; D012266:Ribose; D005947:Glucose; D000241:Adenosine