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

• Matthew B. Plutschack,
• D. Tyler McQuade,
• Giulio Valenti and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2013, 9, 2022–2027, doi:10.3762/bjoc.9.238

• 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

• NBDM, enabling us to measure key photophysical properties that will facilitate future uptake studies. Keywords: flow chemistry; fructose mimic; gluts; NBDM; Introduction The impact of dietary fructose on human health is not well-understood. A growing body of work suggests that those eating diets high

• fewer tissues [2]. We are developing probes that are selectively transported by Glut5. Using design principles gleaned from the Holman group [13][14][15] as well as other fructose analogue research [16], we synthesized NBDM [17] and demonstrated that this probe is transported into cancer cells known to