An improved method for the large scale preparation of α,α′-trehalose-6-phosphate

Liu, Chunliang; Mariano, Patrick S.

doi:10.1016/j.tetlet.2014.10.003

Cited by 6 publications

(7 citation statements)

References 14 publications

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“…The JH1, H2 values of Glc and Glc6P were 3.75 Hz and 3.85 Hz, respectively, which indicated that both pyranoses were in an α-anomeric configuration. The chemical shifts obtained from the 1 H-and 13 C-NMR matched those previously reported for Tre6P [11,12].…”

Section: Resultssupporting

confidence: 85%

“…The Tre6P yield of this enzymatic method was higher than that of the yeast fermentation method (11%) and lower than that of organic synthesis (55%) [10][11][12]. However, the primary advantage of the enzymatic synthesis method established here is the simple synthesis of Tre6P at gram-scale in one-pot reactions from abundantly available starting materials, i.e.…”

Section: Efficiency Improvement Of Tre6p Synthesis Using Yeastmentioning

confidence: 91%

“…To better understand the physiological functions of Tre6P, especially in plants, efficient synthetic methods are required to produce a sufficient amount of Tre6P for analyses. To date, Tre6P has been synthesized by yeast fermentation [10] and organic synthesis [11,12]. In the former system, D-glucose provided as the carbon source is converted into Tre6P with 11% yield.…”

Section: Introductionmentioning

confidence: 99%

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Efficient one-pot enzymatic synthesis of trehalose 6-phosphate using GH65 α-glucoside phosphorylases

Taguchi

Saburi

Imai

et al. 2020

Carbohydrate Research

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Section: Resultssupporting

confidence: 85%

Section: Efficiency Improvement Of Tre6p Synthesis Using Yeastmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Efficient one-pot enzymatic synthesis of trehalose 6-phosphate using GH65 α-glucoside phosphorylases

Taguchi

Saburi

Imai

et al. 2020

Carbohydrate Research

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“…GPC Analysis of CPDs 7 confirmed a very low polydispersity of PDI = 1.03 ± 0.04 and a relatively short length with n = 19 monomers per polymer, resulting in an M w = 9.5 ± 1.2 kDa . The alkynated d ‐glucose 11 was obtained from d ‐glucose 12 by acid catalyzed glycosidation with alkyne 13 following reported procedures . Temporary benzoyl protection was necessary to isolate pure α anomer 11 ( Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…CPDs 14 – 16 were prepared in similarly high yield following the same procedure ( Scheme ). The necessary alkyne substrates 15 – 19 were readily accessible following literature procedures ( Figure , Scheme ) . The original CPDs 2 were prepared for comparison, following the reported procedures optimized to obtain polymers of comparable properties (PDI = 1.22 ± 0.15, n = 19, M w = 9.3 ± 1.4 kDa) …”

Section: Resultsmentioning

confidence: 99%

Glycosylated Cell‐Penetrating Poly(disulfide)s: Multifunctional Cellular Uptake at High Solubility

Morelli

Bartolami

Sakai

et al. 2018

Helvetica Chimica Acta

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In memory of Ronald BreslowThe glycosylation of cell-penetrating poly(disulfide)s (CPDs) is introduced to increase the solubility of classical CPDs and to achieve multifunctional cellular uptake. With the recently developed sidechain engineering, CPDs decorated with a-D-glucose (Glu), b-D-galactose (Gal), D-trehalose (Tre), and triethyleneglycol (TEG) were readily accessible. Confocal laser scanning microscopy images of HeLa Kyoto cells incubated with the new CPDs at 2.5 lM revealed efficient uptake into cytosol and nucleoli of all glycosylated CPDs, whereas the original CPDs and TEGylated CPDs showed much precipitation into fluorescent aggregates at these high concentrations. Flow cytometry analysis identified Glu-CPDs as most active, closely followed by Gal-CPDs and Tre-CPDs, and all clearly more active than nonglycosylated CPDs. In the MTT assay, all glyco-CPDs were non-toxic at concentrations as high as 2.5 lM. Consistent with thiol-mediated uptake, glycosylated CPDs remained dependent on thiols on the cell surface for dynamic covalent exchange, their removal with Ellman's reagent DTNB efficiently inhibited uptake. Multifunctionality was demonstrated by inhibition of Glu-CPDs with D-glucose (IC 50 ca. 20 mM). Insensitivity toward L-glucose and D-galactose and insensitivity of conventional CPDs toward D-glucose supported that glucose-mediated uptake of the multifunctional Glu-CPDs involves selective recognition by glucose receptors at the cell surface. Weaker but significant sensitivity of Gal-CPDs toward D-galactose but not D-glucose was noted (IC 50 ca. 110 mM). Biotinylation of Glu-CPDs resulted in the efficient delivery of streptavidin together with a fluorescent model substrate. Protein delivery with Glu-CPDs was more efficient than with conventional CPDs and remained sensitive to DTNB and D-glucose, i.e., multifunctional.

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Protecting Groups at the Primary Position of Carbohydrates

2018

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An improved method for the large scale preparation of α,α′-trehalose-6-phosphate

Cited by 6 publications

References 14 publications

Efficient one-pot enzymatic synthesis of trehalose 6-phosphate using GH65 α-glucoside phosphorylases

Efficient one-pot enzymatic synthesis of trehalose 6-phosphate using GH65 α-glucoside phosphorylases

Glycosylated Cell‐Penetrating Poly(disulfide)s: Multifunctional Cellular Uptake at High Solubility

Protecting Groups at the Primary Position of Carbohydrates

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