Synthesis of 6′-deoxy-6′-fluorosucrose

Gaddam, Vikram; Harmata, Michael

doi:10.1016/j.carres.2012.12.001

Cited by 7 publications

(8 citation statements)

References 32 publications

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“…To our knowledge, this report is the first fully automated, non-enzymatic approach for the radiofluorination of sucrose. The precursor was developed and labeled with cold fluorine as previously described [ 42 ]. Translation of this chemistry to automated radiosynthesis afforded a decay corrected yield ranging from 1.8 to 23.6% of 18 FS.…”

Section: Resultsmentioning

confidence: 99%

“…No differences in yields were observed whether using K222/K 2 CO 3 or tetraethylammonium bicarbonate (TEAB) in the synthesis. Literature yields for cold labeling of sucrose were reported as >90% [ 42 ]. A common observation when translating cold labeling to radiolabeling is a significant decrease in yield [ 66 – 75 ].…”

Section: Resultsmentioning

confidence: 99%

“…Solvents used for water-sensitive reactions (i.e., CH 3 CN) were anhydrous grade and were stored in Sure/Seal bottles prior to use. The labeling precursor, 6’- O -trifluoromethanesulfonyl-2,3,4,6,1’,3’,4’-hepta- O -benzoylsucrose was prepared according to [ 42 ] and stored under an argon atmosphere and over DrieRite prior to use. Cryptand 222 (cryptofix, K222, etc.)…”

Section: Methodsmentioning

confidence: 99%

“…The enzymatic approach was recently applied to obtain the first 18 F fluorinated derivative, 1’-[ 18 F]fluoro-1’-deoxysucrose, in 26% yield [ 39 ]. We have recently reported the first purely synthetic approaches for the syntheses of 6’-deoxy-6’-fluorosucrose, 1’-deoxy-1’-fluorosucrose, and 6-deoxy-6-fluorosucrose [ 42 – 44 ]. Here, we report the first radiolabeling of sucrose with 18 F at the 6’ position, and the utility of 6’-deoxy-6’[ 18 F]fluorosucrose ( 18 FS) in studying sucrose phloem transport in maize ( Zea mays ) leaves and specifically with sucrose transporter (SUT) proteins.…”

Section: Introductionmentioning

confidence: 99%

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Radiosynthesis of 6’-Deoxy-6’[18F]Fluorosucrose via Automated Synthesis and Its Utility to Study In Vivo Sucrose Transport in Maize (Zea mays) Leaves

et al. 2015

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Sugars produced from photosynthesis in leaves are transported through the phloem tissues within veins and delivered to non-photosynthetic organs, such as roots, stems, flowers, and seeds, to support their growth and/or storage of carbohydrates. However, because the phloem is located internally within the veins, it is difficult to access and to study the dynamics of sugar transport. Radioactive tracers have been extensively used to study vascular transport in plants and have provided great insights into transport dynamics. To better study sucrose partitioning in vivo, a novel radioactive analog of sucrose was synthesized through a completely chemical synthesis route by substituting fluorine-18 (half-life 110 min) at the 6’ position to generate 6’-deoxy-6’[18F]fluorosucrose (18FS). This radiotracer was then used to compare sucrose transport between wild-type maize plants and mutant plants lacking the Sucrose transporter1 (Sut1) gene, which has been shown to function in sucrose phloem loading. Our results demonstrate that 18FS is transported in vivo, with the wild-type plants showing a greater rate of transport down the leaf blade than the sut1 mutant plants. A similar transport pattern was also observed for universally labeled [U-14C]sucrose ([U-14C]suc). Our findings support the proposed sucrose phloem loading function of the Sut1 gene in maize, and additionally demonstrate that the 18FS analog is a valuable, new tool that offers imaging advantages over [U-14C]suc for studying phloem transport in plants.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Radiosynthesis of 6’-Deoxy-6’[18F]Fluorosucrose via Automated Synthesis and Its Utility to Study In Vivo Sucrose Transport in Maize (Zea mays) Leaves

et al. 2015

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“…18 F was produced by the nuclear reaction 18 O(p,n) 18 F using a GE PET Trace cyclotron as described (Rotsch et al, 2015). The precursors (6'-O-Trifluoromethanesulfonyl-2,3,4,6,1',3',4'hepta-O-benzoylsucrose for 6'-[ 18 F]FDS; 1'-O-Trifluoromethanesulfonyl-2,3,4,6,3',4',6'-hepta-O-benzoylsucrose for 1'-[ 18 F]FDS; and 6-O-Trifluoromethanesulfonyl-2,3,4,1',3',4',6'-hepta-Obenzoylsucrose for 6-[ 18 F]FDS ) were prepared as described (Gaddam and Harmata, 2013;Ying et al, 2013;Gao et al, 2014).…”

Section: Radiosynthesis Of [ 18 F]fds Analogsmentioning

confidence: 99%

In vivo transport of three radioactive [18F]-fluorinated deoxysucrose analogs by the maize sucrose transporter ZmSUT1

Trần

Hampton

Brossard

et al. 2017

Plant Physiology and Biochemistry

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Sucrose transporter (SUT) proteins translocate sucrose across cell membranes; however, mechanistic aspects of sucrose binding by SUTs are not well resolved. Specific hydroxyl groups in sucrose participate in hydrogen bonding with SUT proteins. We previously reported that substituting a radioactive fluorine-18 [F] at the C-6' position within the fructosyl moiety of sucrose did not affect sucrose transport by the maize (Zea mays) ZmSUT1 protein. To determine how F substitution of hydroxyl groups at two other positions within sucrose, the C-1' in the fructosyl moiety or the C-6 in the glucosyl moiety, impact sucrose transport, we synthesized 1'-[F]fluoro-1'-deoxysucrose and 6-[F]fluoro-6-deoxysucrose ([F]FDS) analogs. Each [F]FDS derivative was independently introduced into wild-type or sut1 mutant plants, which are defective in sucrose phloem loading. All three (1'-, 6'-, and 6-) [F]FDS derivatives were efficiently and equally translocated, similarly to carbon-14 [C]-labeled sucrose. Hence, individually replacing the hydroxyl groups at these positions within sucrose does not interfere with substrate recognition, binding, or membrane transport processes, and hydroxyl groups at these three positions are not essential for hydrogen bonding between sucrose and ZmSUT1. [F]FDS imaging afforded several advantages compared to [C]-sucrose detection. We calculated that 1'-[F]FDS was transported at approximately a rate of 0.90 ± 0.15 m.h-1 in wild-type leaves, and at 0.68 ± 0.25 m.h-1 in sut1 mutant leaves. Collectively, our data indicated that [F]FDS analogs are valuable tools to probe sucrose-SUT interactions and to monitor sucrose transport in plants.

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