title: Synthesis and structural analysis of a series of D-glucose derivatives as low molecular weight gelators.
abstract: Low molecular weight gelators are an interesting new type of compounds that are important in supramolecular chemistry and advanced materials. Previously, we had synthesized several acyl derivatives of methyl 4,6-O-benzylidene-alpha-D-glucopyranoside and found that a number of terminal acetylene-containing esters are good gelators. To understand the structure requirement of the acyl chains, we synthesized a series of analogs containing different functional groups including aryl, alkenyl, and halogen derivatives. X-ray crystal structures of a monoester and a diester derivative were also obtained to help understand the relationship between structure and gelation. For good gelation properties, the carboxyl derivatives should possess alkyl groups containing a terminal acetylene group and aryl derivatives.
authors.affiliation: Department of Chemistry, University of New Orleans, New Orleans, LA 70148, USA.
authors.forename: Sherwin
authors.initials: S
authors.lastname: Cheuk
authors.forename: Edwin D
authors.initials: ED
authors.lastname: Stevens
authors.forename: Guijun
authors.initials: G
authors.lastname: Wang
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005947:Glucose / Q000031:analogs & derivatives* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D008970:Molecular Weight; D013329:Structure-Activity Relationship
chemical_list: D002241:Carbohydrates; D005947:Glucose