Procurement of 2-deoxy-2-iodo-d-glucose (2-DIG)

Tracking the Biological Incorporation of Exogenous Molecules into Cellulose Fibers with Non‐Radioactive Iodinated Glucose

“…The observed fiber inhibition at higher concentrations of DIG and the yellow coloration observed at the core of the ovules incubated with 0.02 mg/mL DIG can be attributed to the presence of the free iodide slowly being released from DIG. The presence of iodine in the α position to an aldehyde in an open chain form makes elimination favorable [10b,32] …”

“…When combined with in-vitro ovules, these analogs yielded biologically fabricated fibers displaying properties such as fluorescence and superparamagnetism. [8] Radioactive halogenated glucose analogs, such as [ 18 F]-2fluoro-2-deoxy-glucose (FDG), [9] [ 18 F]-3-fluoro-3-deoxyglucose [9c] and I 123 and 125 I-labeled glucose analogs iodinated in positions 2, 3, 4 or 6, [10] have been used as positron emission tomography (PET) contrast agents in clinical oncology and neuroimaging. [11] Due to metabolic and structural (e. g., steric hindrance) considerations, only the glucose moiety halogenated at position C2 has been used for the in-vivo assessment of the glucose transport and uptake rate.…”

“…Radioactive halogenated glucose analogs, such as [ 18 F]‐2‐fluoro‐2‐deoxy‐glucose (FDG), [9] [ 18 F]‐3‐fluoro‐3‐deoxy‐glucose [9c] and I 123 and 125 I‐labeled glucose analogs iodinated in positions 2, 3, 4 or 6, [10] have been used as positron emission tomography (PET) contrast agents in clinical oncology and neuroimaging [11] . Due to metabolic and structural (e. g., steric hindrance) considerations, only the glucose moiety halogenated at position C2 has been used for the in‐vivo assessment of the glucose transport and uptake rate [10a,b, 12] . For example, FDG has been used in combination with PET to image plants, [13] explore the uptake and distribution of glucose in Sorghum bicolor (L.) Moench, [14] photoassimilate the translocation in Arabidopsis thaliana [15] and to biosynthesize glycosides [16] .…”

d-Glucose- and d-mannose-based antimetabolites. Part 2. Facile synthesis of 2-deoxy-2-halo-d-glucoses and -d-mannoses

“…Other reports described this method as difficult to repeat. 36 The most efficient method for the introduction of an iodine substituent at C-2 has been an addition reaction of N-iodosuccinimide to the double bond of D-glucal. Stereochemistry of the addition reaction to differentially protected D-glucal has been studied by several groups, and the 2-deoxy-2-iodo-D-manno isomer appeared to be the predominant product.…”

“…It has been shown that addition of N-iodosuccinimide to 3,4,6-tri-O-(tert-butyldiphenylsilyl)-D-glucal in the presence of acetic acid in toluene at 100°C led to mixture of 1-O-acetyl-2-deoxy-2-iodo-D-gluco-and D-manno isomers with a gluco to manno ratio of 9:1. This method was used by Morin 36 for synthesis of 2-deoxy-2-iodo-a,b-D-glucose. The initial mixture of 1-O-acetyl-2-deoxy-2-iodo-D-gluco and -D-manno isomers was separated by column chromatography, then the silyl ethers were removed by treatment with the HFÁEt 3 N complex at 65°C for 24 h. The last step, deacetylation at the anomeric center, was completed by the method described by Excoffier and co-workers 37 using hydrazine acetate in MeOH.…”