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
PDF
Graphical Abstract
Scheme 1:
Batch synthesis of NBDM. a) NaNO2, Amberlite IR-120 H+ (100 mL), 0 °C, water, 4 h. b) NH2OH·HCl, Na...