Thiophosphate and thiophosphonate analogues of glucose-1-phosphate: synthesis and enzymatic activity with a thymidylyltransferase

Loranger, Matthew W.; Beaton, Stephen A.; Lines, Katie L.; Jakeman, David L.

doi:10.1016/j.carres.2013.06.007

Cited by 15 publications

(5 citation statements)

References 30 publications

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“…The group also reported the first synthesis of a dTDP-Glc-1-thiophosphonate again using Cps2L. 28 A non-scissile glycosyl thiophosphonate analogue (Scheme 10) was evaluated as a Cps2L substrate, forming the desired dTDP-glycosyl thiophosphonate with a 15% conversion rate (ESI-MS confirmed that an O-pyrophosphate had formed). Only one peak was observed by HPLC for the thiophosphonate product, which inferred that Cps2L may distinguish between pro-R and pro-S thiophosphonate oxygen atoms; a similar observation having been made for pro-R and pro-S -monofluorinated phosphonate (Scheme 9).…”

Section: Scheme 8 Synthesis Of Dtdp and Udp Glc And Gal Phosphonate mentioning

confidence: 99%

Recent advances in the enzymatic synthesis of sugar-nucleotides using nucleotidylyltransferases and glycosyltransferases

Ahmadipour

Beswick

Miller

2018

Carbohydrate Research

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Section: Scheme 8 Synthesis Of Dtdp and Udp Glc And Gal Phosphonate mentioning

confidence: 99%

Recent advances in the enzymatic synthesis of sugar-nucleotides using nucleotidylyltransferases and glycosyltransferases

Ahmadipour

Beswick

Miller

2018

Carbohydrate Research

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“…Previous studies have shown that APS is particularly prominent in the treatment of diabetes mellitus, and it is a candidate for insulin resistance therapy [45,46]. Glucose-1-phosphate is the substrate of glycosyl derivatives [47], and it is also an important glycogen synthesized by liver and muscle in adrenal dysfunction [48]. β-aminoisobutyric acid, also known as DL-3-aminoisobutyric acid, is produced in skeletal muscle during exercise.…”

Section: Discussionmentioning

confidence: 99%

Analysis of Astragalus Polysaccharide Intervention in Heat-Stressed Dairy Cows’ Serum Metabolomics

Zeng

et al. 2020

Animals

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This experiment was conducted to investigate the effects of astragalus polysaccharides (APS) on serum metabolism of dairy cows under heat stress. Thirty healthy Holstein dairy cows were randomly divided into three groups (10 cows in each group). In the experimental group, 30 mL/d (Treatment I) and 50 mL/d (Treatment II) of APS injection were injected into the neck muscle respectively. Each stage was injected with APS for 4 days (8:00 a.m. every day) and stopped for 3 days. Serum hormone and antioxidant indexes of dairy cows were investigated. Through repeated measurement analysis of variance, the results have shown that cortisol (COR) (F = 6.982, p = 0.026), triiodothyronine (T3) (F = 10.005, p = 0.012) and thyroxine (T4) (F = 22.530, p = 0.002) at different time points were significantly different. COR showed a downward trend, T3 and T4 showed an upward trend. At each time point, different concentrations of APS have significant effects on COR (F = 30.298, p = 0.000 < 0.05), T3 (F = 18.122, p = 0.001), and T4 (F = 44.067, p = 0.000 < 0.05). However, there were no significant differences in serum insulin (INS), glucagon (GC) and heat shock protein 70 (HSP70) between different time points (p > 0.05) and at each time point (p > 0.05). Additionally, the results have also shown that there were also no significant differences in serum Superoxide dismutase (SOD), malondialdehyde (MDA) and lactate dehydrogenase (LDH) between different time points (p > 0.05) and at each time point (p > 0.05). However, the injection of APS had a significant impact on glutathione peroxidase (GSH-Px) (F = 9.421, p = 0.014) at different times, and showed a trend of rising first and then falling. At each time point, APS of different concentrations had no significant effect on GSH-Px (p > 0.05). Furthermore, we used gas chromatography–mass spectrometry (GC-MS) non-targeted metabolomics to determine the potential markers of APS for heat-stressed dairy cows. Twenty metabolites were identified as potential biomarkers for the diagnosis of APS in heat-stressed dairy cows. These substances are involved in protein digestion and absorption, glutathione metabolism, prolactin signaling pathway, aminoacyl-tRNA biosynthesis, pentose and glucuronate interconversions, and so on. Our findings suggest that APS have an effect on the serum hormones of heat-stressed dairy cows, and regulate the metabolism of heat-stressed dairy cows through glucose metabolism and amino acid metabolism pathways.

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“…Thiophosphinates are important building blocks used not only as synthetic intermediates, but also for the synthesis of biologically active molecules. 1,29 Thus, several synthetic methods for thiophosphinates have been reported recently, 30 and a number of synthetic routes to selenophosphinates have also been developed. 31 Nevertheless, the present reaction is considered advantageous in terms of easy operation.…”

Section: Methodsmentioning

confidence: 99%

Photoinduced Coupling Reaction of Diphenyl(2,4,6-trimethylbenzoyl)phosphine Oxide with Interelement Compounds: Application to the Synthesis of Thio- or Selenophosphinates

2017

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Diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TMDPO) is a radical initiator widely used in the field of macromolecular chemistry, but not often applied in synthetic organic chemistry. We have focused on the use of TMDPO as a phosphorus source in reactions with different E – E compounds, where E – E represents a heteroatom–heteroatom bond, under photoirradiation. Interestingly, the cross-coupling reaction between TMDPO and disulfides or diselenides successfully affords thio- or selenophosphinates and thio- or selenoesters, respectively. The synthesis of series of thio- and selenophosphinates by this photoinduced cross-coupling reaction is demonstrated.

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Thiophosphate and thiophosphonate analogues of glucose-1-phosphate: synthesis and enzymatic activity with a thymidylyltransferase

Cited by 15 publications

References 30 publications

Recent advances in the enzymatic synthesis of sugar-nucleotides using nucleotidylyltransferases and glycosyltransferases

Recent advances in the enzymatic synthesis of sugar-nucleotides using nucleotidylyltransferases and glycosyltransferases

Analysis of Astragalus Polysaccharide Intervention in Heat-Stressed Dairy Cows’ Serum Metabolomics

Photoinduced Coupling Reaction of Diphenyl(2,4,6-trimethylbenzoyl)phosphine Oxide with Interelement Compounds: Application to the Synthesis of Thio- or Selenophosphinates

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