title: Flow synthesis of a versatile fructosamine mimic and quenching studies of a fructose transport probe.
abstract: We describe the synthesis of 1-amino-2,5-anhydro-D-mannose ("mannitolamine"), a key intermediate to the 7-nitro-1,2,3-benzadiazole conjugate (NBDM), using commercially available fluidic devices to increase the throughput. The approach is the first example of a flow-based Tiffeneau-Demjanov rearrangement. Performing this step in flow enables a ~64-fold throughput enhancement relative to batch. The flow process enables the synthesis to be accomplished three times faster than the comparable batch route. The high throughput enabled the production of larger quantities of the fluorescent fructose transport probe NBDM, enabling us to measure key photophysical properties that will facilitate future uptake studies.
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306, USA ; Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany.
authors.forename: Matthew B
authors.initials: MB
authors.lastname: Plutschack
authors.forename: D Tyler
authors.initials: DT
authors.lastname: McQuade
authors.forename: Giulio
authors.initials: G
authors.lastname: Valenti
authors.forename: Peter H
authors.initials: PH
authors.lastname: Seeberger
keywords: NBDM; flow chemistry; fructose mimic; gluts