Stereochemical and Regiochemical Trends in the Selective Detection of Saccharides
- 25 August 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (37), 12221-12228
- https://doi.org/10.1021/ja063651p
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.Keywords
This publication has 34 references indexed in Scilit:
- Ratio of Maltose to Maltulose and Furosine as Quality Parameters for Infant FormulaJournal of Agricultural and Food Chemistry, 2004
- Molecular Clips Form Isostructural Dimeric Aggregates from Benzene to WaterJournal of the American Chemical Society, 2004
- The role of ribose in human skeletal muscle metabolismMedical Hypotheses, 2004
- A novel inhibitory effect of d-allose on production of reactive oxygen species from neutrophilsJournal of Bioscience and Bioengineering, 2003
- Tetraarylboronic Acid Resorcinarene Stereoisomers. Versatile New Substrates for Divergent Polyfunctionalization and Molecular RecognitionThe Journal of Organic Chemistry, 1997
- A 5‘-(Trifluoromethyl)anthracycline Glycoside: Synthesis of Antitumor-Active 7-O-(2,6-Dideoxy-6,6,6-trifluoro-α-l-lyxo-hexopyranosyl)adriamycinoneJournal of Medicinal Chemistry, 1996
- Stabilization of Sugar-Boronic Esters of Indolylboronic Acid in Water via Sugar–Indole Interaction: A Notable Selectivity in OligosaccharidesBulletin of the Chemical Society of Japan, 1993
- Specific complexation of glucose with a diphenylmethane-3,3′-diboronic acid derivative: correlation between the absolute configuration of mono- and di-saccharides and the circular dichroic activity of the complexJournal of the Chemical Society, Perkin Transactions 1, 1993
- SCREENING OF CORD BLOOD LOW‐DENSITY‐LIPOPROTEIN CHOLESTEROL IN THE DIAGNOSIS OF FAMILIAL HYPERCHOLESTEROLAEMIA: A STUDY OF 2000 INFANTSActa Paediatrica, 1979
- The Preparation of l-Ribose1,2,3Journal of the American Chemical Society, 1934