Work

Flow synthesis of a versatile fructosamine mimic and quenching studies of a fructose transport probe

Year: 2013

Type: article

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.

Source: Beilstein Journal of Organic Chemistry

DOI: 10.3762/bjoc.9.238

Authors: Matthew B Plutschack, D Tyler McQuade, Giulio Valenti, Peter H Seeberger

Institutions: Florida State University, Max Planck Society, Max Planck Institute of Colloids and Interfaces

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: National Science Foundation, Max-Planck-Gesellschaft, Division of Chemistry

Awards: G1162950679, Efficient Reactions - Selective Cu(I) Catalysts