- Effect of Photocaged Isopropyl β-d-1-thiogalactopyranoside Solubility on the Light Responsiveness of LacI-controlled Expression Systems in Different Bacteria
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Photolabile protecting groups play a significant role in controlling biological functions and cellular processes in living cells and tissues, as light offers high spatiotemporal control, is non-invasive as well as easily tuneable. In the recent past, photo-responsive inducer molecules such as 6-nitropiperonyl-caged IPTG (NP-cIPTG) have been used as optochemical tools for Lac repressor-controlled microbial expression systems. To further expand the applicability of the versatile optochemical on-switch, we have investigated whether the modulation of cIPTG water solubility can improve the light responsiveness of appropriate expression systems in bacteria. To this end, we developed two new cIPTG derivatives with different hydrophobicity and demonstrated both an easy applicability for the light-mediated control of gene expression and a simple transferability of this optochemical toolbox to the biotechnologically relevant bacteria Pseudomonas putida and Bacillus subtilis. Notably, the more water-soluble cIPTG derivative proved to be particularly suitable for light-mediated gene expression in these alternative expression hosts.
- Hogenkamp, Fabian,Hilgers, Fabienne,Knapp, Andreas,Klaus, Oliver,Bier, Claus,Binder, Dennis,Jaeger, Karl-Erich,Drepper, Thomas,Pietruszka, J?rg
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- One-Pot Relay Glycosylation
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A novel one-pot relay glycosylation has been established. The protocol is characterized by the construction of two glycosidic bonds with only one equivalent of triflic anhydride. This method capitalizes on the in situ generated cyclic-thiosulfonium ion as the relay activator, which directly activates the newly formed thioglycoside in one pot. A wide range of substrates are well-accommodated to furnish both linear and branched oligosaccharides. The synthetic utility and advantage of this method have been demonstrated by rapid access to naturally occurring phenylethanoid glycoside kankanoside F and resin glycoside merremoside D.
- Cai, Lei,Fang, Jing,Li, Ting,Song, Zejin,Sun, Jiuchang,Wan, Qian,Xiao, Xiong,Zeng, Jing
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supporting information
p. 5498 - 5503
(2020/04/09)
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- Photocatalysis Enables Visible-Light Uncaging of Bioactive Molecules in Live Cells
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The photo-manipulation of bioactive molecules provides unique advantages due to the high temporal and spatial precision of light. The first visible-light uncaging reaction by photocatalytic deboronative hydroxylation in live cells is now demonstrated. Using Fluorescein and Rhodamine derivatives as photocatalysts and ascorbates as reductants, transient hydrogen peroxides were generated from molecular oxygen to uncage phenol, alcohol, and amine functional groups on bioactive molecules in bacteria and mammalian cells, including neurons. This effective visible-light uncaging reaction enabled the light-inducible protein expression, the photo-manipulation of membrane potentials, and the subcellular-specific photo-release of small molecules.
- Wang, Haoyan,Li, Wei-Guang,Zeng, Kaixing,Wu, Yan-Jiao,Zhang, Yixin,Xu, Tian-Le,Chen, Yiyun
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supporting information
p. 561 - 565
(2019/01/04)
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- Isopropyl - β - D thio-galactopyranoside synthetic method (by machine translation)
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The present invention provides a kind of isopropyl - β - D thio-galactopyranoside synthetic method, namely the method for synthesis of IPTG. Comprises the following steps: five acetyl galactose as raw materials, with the thiourea reaction to obtain the acetyl S - galactose isothiourea fluoro salt, then with the pyrosulfites reaction to obtain the acetyl S - galactose, with isopropyl bromide reaction, the final deacetyl get the compound goal isopropyl - β - D thio-galactopyranoside. In the whole in the reaction process mainly selects the five acetyl galactose and isopropyl bromide as the raw material, not required to be selected smell, toxic isopropyl mercaptan, effectively avoiding harm to human health and the environment, in addition the invention has simple operation, high yield, purity and the like. Is suitable for industrial production. (by machine translation)
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Paragraph 0013; 0031; 0038-0039
(2018/03/26)
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- Method for synthesizing isopropyl-beta-D-thiogalactoside (IPTG)
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The invention provides a method for synthesizing isopropyl-beta-D-thiogalactoside (IPTG) and belongs to the technical field of organic synthesis. The method comprises the following steps: taking a compound beta-D-galactose pentaacetate as a raw material, and reacting with potassium ethyl xanthate in the presence of a catalyst so as to obtain tetraacetyl galactose ethyl xanthate; reacting with 2-bromopropane under an alkaline condition, so as to obtain the isopropyl-beta-D-thiogalactoside (IPTG). According to the synthetic method, the beta-D-galactose pentaacetate, potassium ethyl xanthate and2-bromopropane are taken as main raw materials, 2-mercaptopropane which is extremely unpleasant in smell, easy to diffuse and high in toxicity used in the original method is replaced, and the harm tothe environment is effectively avoided. The raw materials used in the method disclosed by the invention are readily available, the operating process is simple and convenient, the reaction condition ismild, and the method is safe, controllable and high in yield.
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Paragraph 0017; 0018; 0019; 0020
(2018/11/22)
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- A preparation of isopropyl-β-D-thio-galactopyranoside method (by machine translation)
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Field of the invention relates to sugar compounds, in particular relates to a preparation of isopropyl-β-D-thio-galactopyranoside method. By adding acetic anhydride and catalyst at room temperature, by adding galactose, after the completion of reaction, adding heteroploid propanethiol, after the reaction is finished after post-processed to obtain isopropylacrylamides thiophosphoro acetyl galactose. ? The isopropyl thio-acetyl galactose added to the methanol solution, adding sodium methoxide, ? After the reaction is finished adding acetic acid neutralization, after post-processed to obtain isopropyl-β-D-thio-galactopyranoside. The method of the invention by the two-step reaction process for synthesizing isopropyl-β-D-thio-galactopyranoside, the operation is simple, easy availability of raw materials, saving the operation cost and material. (by machine translation)
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Paragraph 0032; 0034; 0036
(2017/04/05)
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- Isopropyl-β-D-thio-galactopyranoside preparation method (by machine translation)
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Field of the invention relates to sugar compounds, in particular relates to a preparation of isopropyl? Β? D? Thio-galactopyranoside method. By adding acetic anhydride and catalyst at room temperature, by adding galactose, after the completion of reaction, adding heteroploid propanethiol, after the reaction is finished after post-processed to obtain isopropylacrylamides thiophosphoro acetyl galactose. The isopropyl thio-acetyl galactose added to the methanol solution, adding sodium methoxide, after the completion of reaction is neutralized by adding acetic acid, after post-processed to obtain isopropylacrylamides? Β? D? Thio-galactopyranoside. The method of the invention by the two-step reaction process for synthesizing isopropylacrylamides? Β? D? Thio-galactopyranoside, the operation is simple, easy availability of raw materials, saving the operation cost and material. (by machine translation)
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Paragraph 0021; 0023
(2017/04/11)
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- A isopropyl-β-D-thio-galactopyranoside process for preparing
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The invention relates to the field of saccharide compounds, particularly a preparation technique of isopropyl-beta-D-thiogalactoside. The technique comprises the following steps: adding acetic anhydride and a catalyst at room temperature, and adding galactose; after the reaction finishes, adding isopropyl mercaptan; after the reaction finishes, carrying out after-treatment to obtain isopropyl thioacetyl galactose; dissolving the isopropyl thioacetyl galactose in methanol, and adding sodium methoxide; and after the reaction finishes, adding acetic acid for neutralization, and carrying out after-treatment to obtain the isopropyl-beta-D-thiogalactoside. The method synthesizes the isopropyl-beta-D-thiogalactoside by a two-step reaction process, is simple to operate and accessible in raw materials, and saves the operating cost and materials.
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Paragraph 0020; 0022
(2017/03/14)
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- Isopropyl-β-D-thio-galactopyranoside process for preparing
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The invention relates to the field of sugar compounds, and concretely relates to an isopropyl-beta-D-thiogalactoside preparation technology. The technology comprises the following steps: adding acetic anhydride and a catalyst at room temperature, adding galactose, adding isopropyl mercaptan after the above reaction, and post-processing to obtain isopropyl thioacetylgalactosamine; and adding isopropyl thioacetylgalactosamine into methanol for dissolving, adding sodium methoxide, adding acetic acid after the above reaction to neutralize, and post-processing to obtain isopropyl-beta-D-thiogalactoside. The technology allows isopropyl-beta-D-thiogalactoside to be synthesized through a two-step reaction process, and has the advantages of simple operation, easily available raw materials, and saving of the operation cost and materials.
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Paragraph 0027-0029
(2017/04/27)
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- Preparation of isopropyl-β-D-thio-galactopyranoside method
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The invention relates to the field of saccharide compounds, particularly a method for preparing isopropyl-beta-D-thiogalactoside. The method comprises the following steps: adding acetic anhydride and a catalyst at room temperature, and adding galactose; after the reaction finishes, adding isopropyl mercaptan; after the reaction finishes, carrying out after-treatment to obtain isopropyl thioacetyl galactose; dissolving the isopropyl thioacetyl galactose in methanol, and adding sodium methoxide; and after the reaction finishes, adding acetic acid for neutralization, and carrying out after-treatment to obtain the isopropyl-beta-D-thiogalactoside. The method synthesizes the isopropyl-beta-D-thiogalactoside by a two-step reaction process, is simple to operate and accessible in raw materials, and saves the operating cost and materials.
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Paragraph 0041; 0043-0045
(2017/03/17)
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- Preparation method for isopropyl-beta-D-thiogalactopyranoside
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The invention discloses a preparation method for isopropyl-beta-D-thiogalactopyranoside. The preparation method comprises the following steps: putting acetic anhydride in a reaction furnace, adding D-galactose, then adding potassium acetate and isopropyl mercaptan, and reacting at 75 to 85 DEG C for 24 to 48 hours; distilling; adding methylene dichloride and water after temperature is cooled to 35 to 45 DEG C, performing stirring reaction, standing, and cooling to room temperature; then adding water and stirring, standing, repeating three times and ensuring a pH (potential of hydrogen) value of a material to be about 7; putting the material in the reaction furnace, adding sodium carbonate, diluting by water and stirring; drying, refluxing and distilling; adding ethyl alcohol, performing stirring reaction at 65 to 75 DEG C, refluxing for 20 to 28 hours to obtain a crystalline solid; crystallizing, filtering and drying to obtain the isopropyl-beta-D-thiogalactopyranoside. The preparation method disclosed by the invention has a simple preparation process; by taking the acetic anhydride, the D-galactose and the isopropyl mercaptan as raw materials, under catalytic action of potassium acetate, the prepared isopropyl-beta-D-thiogalactopyranoside is high in yield and very stable in quality, and has a broad application prospect.
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Paragraph 0031; 0032; 0033; 0034; 0035; 0036; 0037; 0038
(2016/12/01)
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- Concise syntheses of arabinogalactans with β-(1→6)-linked galactopyranose backbones and α-(1→3)- and α-(1→2)-linked arabinofuranose side chains
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4-Methoxyphenyl glycosides of 2,3″-bis-α-l-arabinofuranosyl branched β-d-(1→6)-linked galactopyranosyl tetraose (16), 3′,2″″-bis-α-l-arabinofuranosyl branched β-d-(1→6)-linked galactopyranosyl hexaose (27), and a twentyose (42) consisting of β-(1→6)-linked d-galactopyranosyl pentadecaoligosaccharide backbone with α-l-arabinofuranosyl side chains alternately attached at C-2 and C-3 of the middle galactose residue of each consecutive β-(1→6)-linked galactotriose unit of the backbone, were synthesized with isopropyl 3-O-allyl-2,4-di-O-benzoyl-1-thio-β-d- galactopyranoside (6), 2,3,4,6-tetra-O-benzoyl-α-d-galactopyranosyl trichloroacetimidate (7), 2,3,5-tri-O-benzoyl-α-l-arabinofuranosyl trichloroacetimidate (12), 6-O-acetyl-2,3,4-tri-O-benzoyl-α-d- galactopyranosyl trichloroacetimidate (17), 4-methoxyphenyl 2,3,4-tri-O-benzoyl- β-d-galactopyranoside (19), and 2,6-di-O-acetyl-3,4-di-O-benzoyl-α-d- galactopyranosyl trichloroacetimidate (28) as the key synthons. Condensation of 6 with 7 gave the disaccharide donor 8, and subsequent condensation of 8 with 4-methoxyphenyl 2,3,4-tri-O-benzoyl-β-d-galactopyranosyl-(1→6)-2-O- acetyl-3,4-di-O-benzoyl-β-d-galactopyranoside (9) followed by selective deacetylation afforded the tetrasaccharide acceptor 11. Coupling of 11 with 12 gave the pentasaccharide 13, its deallylation followed by coupling with 12, and debenzoylation gave the hexasaccharide 16 with β-(1→6)-linked galactopyranose backbone and 2- and 3″-linked α-l-arabinofuranose side chains. The octasaccharide 27 was similarly synthesized, while the twentyoside 42 was synthesized with tetrasaccharides 33 or 24 as the donors and 23, 36, 38, and 40 as the acceptors by consecutive couplings followed by deacylation.
- Li, Aixiao,Kong, Fanzuo
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p. 839 - 853
(2007/10/03)
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- Preparations and reactions of acylated and partially acylated glycosyl fluorides
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Partial acylation of glycosyl fluorides in the galacto (2 and 3) and gluco series (8-10) is readily achieved. Attempts to further alkylate these acyl derivatives failed. Treatment of 2 with Lewis acid, however, provided a facile route to the 1,4-anhydro derivative 5. Lewis acid-mediated glycosylation of 2-acetamido-3,4,6-tri-O-acetyl-α-D-glucopyranosyl fluoride 11 led to the simple glycosides and thioglycosides 12-16. Similarly, in the galacto series (17) an advantageous route to the β-galactosidase inhibitor 19 could be elaborated.
- Thiem, Joachim,Wiesner, Matthias
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p. 197 - 206
(2007/10/02)
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- Glycosylimidates, 8. - Synthesis of 1-Thioglycosides
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As expected, the reactive acetyl-protected O-(α-D-glucopyranosyl) trichloroacetimidate 3 reacts with S-nucleophiles and trifluoroborane-ether as catalyst to yield exclusively 1-thio-β-D-glucopyranosides with inversion of the configuration.The corresponding benzyl-protected α-trichloroacetimidate 4 affords with retention of the configuration alkyl 1-thio-α-D-glucopyranosides.The importance of alkyl 1-thio-β-D-galactopyranosides in enzyme induction was reason to apply this convenient and efficient glycosyl-transfer reaction to the synthesis of isopropyl 1-thio-β-D-galactopyranoside (12a) and the sodium salt of 1-thio-β-D-galactopyranose (12b), respectively.
- Schmidt, Richard R.,Stumpp, Michael
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p. 1249 - 1256
(2007/10/02)
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