- Synthesis of glycosylamines: Identification and quantification of side products
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The synthesis of some glycosylamines (1-amino-1-deoxy-D-glucose, 1-amino-1-deoxy- D-galactose and 1-amino-1-deoxylactose) was carried out by treatment of the corresponding reducing sugars with ammonium hydrogencarbonate in concentrated ammonia. The reaction mixture was first analyzed by capillary electrophoresis with indirect absorbance detection and high performance anion-exchange chromatography with pulsed amperometric detection. Beside glycosylcarbamate, a known reaction by-product, fructose and lactulose were detected during the synthesis of 1-amino-1-deoxyglucose and 1-amino-1-deoxylactose, respectively. Quantification of glycosylamines was carried out by micellar electrokinetic chromatography with UV detection of their 9-fluorenylmethyloxycarbonyl (Fmoc) derivatives; lactulosylamine was thus detected in the synthesis mixture of 1-amino-1-deoxylactose. The Fmoc-glycosylamines were easily purified from the other components of the crude synthesis mixtures.
- Campa, Cristiana,Donati, Ivan,Vetere, Amedeo,Gamini, Amelia,Paoletti, Sergio
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- Synthesis and immunostimulatory activity of sugar-conjugated TLR7 ligands
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Toll-like receptors (TLRs) are a type of pattern recognition receptors (PRRs), which are activated by recognizing pathogen-associated molecular patterns (PAMPs). The activation of TLRs initiates innate immune responses and subsequently leads to adaptive immune responses. TLR agonists are effective immuomodulators in vaccine adjuvants for infectious diseases and cancer immunotherapy. In exploring hydrophilic small molecules of TLR7 ligands using the cell-targeted property of a vaccine adjuvant, we conjugated 1V209, a small TLR7 ligand molecule, with various low or middle molecular weight sugar molecules that work as carriers. The sugar-conjugated 1V209 derivatives showed increased water solubility and higher immunostimulatory activity in both mouse and human cells compared to unmodified 1V209. The improved immunostimulatory potency of sugar-conjugates was attenuated by an inhibitor of endocytic process, cytochalasin D, suggesting that conjugation of sugar moieties may enhance the uptake of TLR7 ligand into the endosomal compartment. Collectively our results support that sugar-conjugated TLR7 ligands are applicable to novel drugs for cancer and vaccine therapy.
- Baba, Akihito,Wakao, Masahiro,Shinchi, Hiroyuki,Chan, Michael,Hayashi, Tomoko,Yao, Shiyin,Cottam, Howard B.,Carson, Dennis A.,Suda, Yasuo
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supporting information
(2019/12/27)
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- 7-nitrobenzo-2-oxa-1, 3-diazole deoxyglucosamine as well as preparation method and application of 7-nitrobenzo-2-oxa-1, 3-diazole deoxyglucosamine
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The invention discloses following three 7-nitrobenzo-2-oxa-1, 3-diazole (NBD) deoxyglucosamine (NBDG) compounds as well as pharmaceutically acceptable salts, a preparation method and an application thereof. The key point of the invention is that the following compounds are deoxyglucose analogues with fluorescein, are used for monitoring glucose uptake of living cell tissues, are one of indexes forjudging cell viability, are used for monitoring local tumor formation, and can also be used as high-sensitivity fluorescent markers in a glucose transport detection method.
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Paragraph 0030; 0032-0034
(2020/07/06)
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- Glycosyl dithiocarbamate as well as preparation method and application thereof
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The invention discloses glycosyl dithiocarbamate as well as a preparation method and an application thereof. The glycosyl dithiocarbamate is of the structure of formula I as shown in the specification, in the formula I, R is glycosyl; M is selected from an alkali metal ion and an ammonium ion. The glycosyl dithiocarbamate provided by the invention is applied to a surface glycosylated material obtained through self-assembly program modification, is good in sugar biological activity at a protein level and is capable of achieving specific recognition. As natural sugar is adopted as a glycosylation substrate, the preparation method of the material is simple, gentle in condition, high in operability, good in reproducibility and wide applicability.
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Paragraph 0048; 0049
(2017/01/17)
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