title: Stereochemical and regiochemical trends in the selective detection of saccharides.
abstract: 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.
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, USA.
authors.forename: Shan
authors.initials: S
authors.lastname: Jiang
authors.forename: Jorge O
authors.initials: JO
authors.lastname: Escobedo
authors.forename: Kyu Kwang
authors.initials: KK
authors.lastname: Kim
authors.forename: Onur
authors.initials: O
authors.lastname: Alptürk
authors.forename: George K
authors.initials: GK
authors.lastname: Samoei
authors.forename: Sayo O
authors.initials: SO
authors.lastname: Fakayode
authors.forename: Isiah M
authors.initials: IM
authors.lastname: Warner
authors.forename: Oleksandr
authors.initials: O
authors.lastname: Rusin
authors.forename: Robert M
authors.initials: RM
authors.lastname: Strongin
mesh_terms: 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
chemical_list: D001897:Boronic Acids; D009005:Monosaccharides; D009705:Nucleosides; D009711:Nucleotides; D009844:Oligosaccharides; C003243:psicose; D005632:Fructose; C002055:allose; D012266:Ribose; D005947:Glucose; D000241:Adenosine