Chemical Synthesis of 1′-Deoxy-1′-fluorosucrose

Ying, Weijiang; Gaddam, Vikram; Harmata, Michael

doi:10.1021/ol401044h

Cited by 10 publications

(9 citation statements)

References 12 publications

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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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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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“…Radioactively Labeled Sucrose Transport Assays 14 C-sucrose was purchased from PerkinElmer (USA), while 1 0 -18 F-sucrose was radiosynthesized as described (Ying et al, 2013;Rotsch et al, 2015). Radioactively labeled sucrose transport assays were performed as previously described on 4-to 5-week-old plants (Slewinski et al, 2009;.…”

Section: Photosynthesis Gas Exchange and Chlorophyll Content Measurementsmentioning

confidence: 99%

Maize Carbohydrate Partitioning Defective33 Encodes an MCTP Protein and Functions in Sucrose Export from Leaves

et al. 2019

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To sustain plant growth, development, and crop yield, sucrose must be transported from leaves to distant parts of the plant, such as seeds and roots. To identify genes that regulate sucrose accumulation and transport in maize (Zea mays), we isolated carbohydrate partitioning defective33 (cpd33), a recessive mutant that accumulated excess starch and soluble sugars in mature leaves. The cpd33 mutants also exhibited chlorosis in the leaf blades, greatly diminished plant growth, and reduced fertility. Cpd33 encodes a protein containing multiple C2 domains and transmembrane regions. Subcellular localization experiments showed the CPD33 protein localized to plasmodesmata (PD), the plasma membrane, and the endoplasmic reticulum. We also found that a loss-of-function mutant of the CPD33 homolog in Arabidopsis, QUIRKY, had a similar carbohydrate hyperaccumulation phenotype. Radioactively labeled sucrose transport assays showed that sucrose export was significantly lower in cpd33 mutant leaves relative to wild-type leaves. However, PD transport in the adaxial-abaxial direction was unaffected in cpd33 mutant leaves. Intriguingly, transmission electron microscopy revealed fewer PD at the companion cell-sieve element interface in mutant phloem tissue, providing a possible explanation for the reduced sucrose export in mutant leaves. Collectively, our results suggest that CPD33 functions to promote symplastic transport into sieve elements.

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“…In the context of our interest in examining sucrose transport in plants, we recently reported syntheses of both 6'-deoxy-6'-fluorosucrose 1 and 1'-deoxy-1'-fluorosucrose. 2 These compounds are currently being used in their "hot" ( 18 F) form in imaging studies concerning sucrose transport in maize. 3 In order to get more complete information on the nature of sucrose transport, we require a sucrose derivative that is functionalized in the glucose half of the molecule.…”

Section: Introductionmentioning

confidence: 99%

A synthesis of 6-deoxy-6-fluorosucrose suitable for PET applications

Gao

Gaddam

Harmata

2014

Carbohydrate Research

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Chemical Synthesis of 1′-Deoxy-1′-fluorosucrose

Abstract: The first chemical synthesis of 1'-deoxy-1'-fluorosucrose has been accomplished in eight steps from sucrose by an unlikely, but ultimately successful, SN2 displacement reaction.

Cited by 10 publications

References 12 publications

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

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

Maize Carbohydrate Partitioning Defective33 Encodes an MCTP Protein and Functions in Sucrose Export from Leaves

A synthesis of 6-deoxy-6-fluorosucrose suitable for PET applications

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