18968-05-3Relevant articles and documents
Disulfide dimannose-gold nanoprobe as well as preparation method and application thereof
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Paragraph 0030-0033, (2021/03/05)
The invention belongs to the field of carbohydrate chemistry biology, and particularly relates to a disulfide dimannose-gold nanoprobe, a preparation method and application of the disulfide dimannose-gold nanoprobe in the aspect of virus receptor DC-SIGN/R recognition. The disulfide dimannose-gold nanoprobe is characterized in that a ligand exchange method is adopted, and disulfide dimannose ligands are modified on the surfaces of gold nanoparticles. The method is based on click chemistry and ligand exchange, modifies the surface of the gold nanoparticle with a mannose ligand to construct a novel dithiodimannose-gold nanoprobe, a sugar binding mechanism of tetramer lectin DC-SIGN and DC-SIGNR is researched on the basis of a fluorescence quenching strategy, and a foundation is laid for establishing a rapid and sensitive method and researching binding affinity and thermodynamics between protein-sugar multivalent interactions.
Synthesis, photophysical properties, and photodynamic activity of positional isomers of TFPP-glucose conjugates
Fadlan, Arif,Tanimoto, Hiroki,Ito, Tatsuya,Aritomi, Yusuke,Ueno, Maho,Tokuda, Masaya,Hirohara, Shiho,Obata, Makoto,Morimoto, Tsumoru,Kakiuchi, Kiyomi
, p. 1848 - 1858 (2018/03/06)
The synthesis and characterization of a ‘complete set’ of positional isomers of tetrakis(perfluorophenyl)porphyrins (TFPP)-glucose conjugates (1OH, 2OH, 3OH, 4OH, and 6OH) are reported herein. The cellular uptake and photocytotoxicity of these conjugates were examined in order to investigate the influence of location of the TFPP moiety on the D-glucose molecule on the biological activity of the conjugates. An In vitro biological evaluation revealed that the certain of these isomers have a greater effect on cellular uptake and cytotoxicity than others. The TFPP-glucose conjugates 1OH, 3OH, and 4OH were found to exert exceptional photocytotoxicity in several types of cancer cells compared to 2OH and 6OH substituted isomers.
A process for the purification of three fluorine mannose intermediate
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Paragraph 0029, (2017/03/17)
The invention provides a method for purifying a 1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose intermediate. The method comprises the following steps: adding a crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product into mixed liquid containing n-butyl alcohol and 2-methoxyethanol; heating the crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product until the crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product is dissolved; cooling the crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product until the crude 1,3,4,6-tetraacetyl-beta-D-mannopyranose product is completely crystallized; performing filtering, washing and drying to obtain the 1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose intermediate, namely a 1,3,4,6-tetraacetyl-beta-D-mannopyranose crystal. The yield and purity of the 1,3,4,6-tetraacetyl-beta-D-mannopyranose are remarkably improved, so that the problems of low yield and low purity of the synthesized 1,3,4,6-tetra-O-acetyl-2-O-triflat-beta-D-mannopyranose intermediate namely 1,3,4,6-tetraacetyl-beta-D-mannopyranose in the prior art are solved.
A convenient and efficient synthetic approach to mono-, di-, and tri-O-mannosylated Fmoc amino acids
Chen, Liqun,Tan, Zhongping
, p. 2190 - 2193 (2013/04/24)
A convenient and highly efficient synthesis of mono-, di-, and tri-O-mannosylated Fmoc-Ser and Thr is described. The short synthetic route and high overall yield highlight the synthetic utility of this unified approach.
3,4,6-Tri-O-acetyl-1,2-O-[1-(exo-ethoxy)ethyl-idene]-Β-d-manno- pyranose 0.11-hydrate
Liu, Ya-Ling,Zou, Pei,Wu, Hao,Xie, Min-Hao,Luo, Shi-Neng
, p. o338-o340 (2012/11/13)
The title compound, C16H24O10·0. 11H2O, is a key inter-mediate in the synthesis of 2-de-oxy-2-[ 18F]fluoro-d-glucose (18F-FDG), which is the most widely used mol-ecular-imaging probe for positron emission tomography (PET). The crystal structure has two independent mol-ecules (A and B) in the asymmetric unit, with closely comparable geometries. The pyran-ose ring adopts a 4 C 1 conformation [Cremer-Pople puckering parameters: Q = 0.553 (2) A?, = 16.2 (2)° and = 290.4 (8)° for mol-ecule A, and Q = 0.529 (2) A?, =15.3 (3)° and = 268.2 (9)° for mol-ecule B], and the dioxolane ring adopts an envelope conformation. The chiral centre in the dioxolane ring, introduced during the synthesis of the compound, has an R configuration, with the eth-oxy group exo to the manno-pyran-ose ring. The asymmetric unit also contains one water mol-ecule with a refined site-occupancy factor of 0.222 (8), which bridges between mol-ecules A and B via O - H?O hydrogen bonds.
A biosynthetic pathway for BE-7585A, a 2-thiosugar-containing angucycline-type natural product
Sasaki, Eita,Ogasawara, Yasushi,Liu, Hung-Wen
experimental part, p. 7405 - 7417 (2010/08/05)
Sulfur is an essential element found ubiquitously in living systems. However, there exist only a few sulfur-containing sugars in nature and their biosyntheses have not been studied. BE-7585A produced by Amycolatopsis orientalis subsp. vinearia BA-07585 has a 2-thiosugar and is a member of the angucycline class of compounds. We report herein the results of our initial efforts to study the biosynthesis of BE-7585A. Spectroscopic analyses verified the structure of BE-7585A, which is closely related to rhodonocardin A. Feeding experiments using 13C-labeled acetate were carried out to confirm that the angucycline core is indeed polyketide-derived. The results indicated an unusual manner of angular tetracyclic ring construction, perhaps via a Baeyer-Villiger type rearrangement. Subsequent cloning and sequencing led to the identification of the bex gene cluster spanning ~30 kbp. A total of 28 open reading frames, which are likely involved in BE-7585A formation, were identified in the cluster. In view of the presence of a homologue of a thiazole synthase gene (thiG), bexX, in the bex cluster, the mechanism of sulfur incorporation into the 2-thiosugar moiety could resemble that found in thiamin biosynthesis. A glycosyltransferase homologue, BexG2, was heterologously expressed in Escherichia coli. The purified enzyme successfully catalyzed the coupling of 2-thioglucose 6-phoshate and UDP-glucose to produce 2-thiotrehalose 6-phosphate, which is the precursor of the disaccharide unit in BE-7585A. On the basis of these genetic and biochemical experiments, a biosynthetic pathway for BE-7585A can now be proposed. The combined results set the stage for future biochemical studies of 2-thiosugar biosynthesis and BE-7585A assembly.
Synthesis and cytotoxic properties of new fluorodeoxyglucose-coupled chlorambucil derivatives
Reux, Bastien,Weber, Valerie,Galmier, Marie-Josephe,Borel, Michele,Madesclaire, Michel,Madelmont, Jean-Claude,Debiton, Eric,Coudert, Pascal
, p. 5004 - 5020 (2008/12/21)
Frequently used in the treatment of malignant cells, alkylating agents, like most anticancer substances, produce adverse side effects caused by the toxicity of the agents toward normal tissues and lose efficiency through poor distribution to target sites.
Immunogenic glycopeptides, screening, preparation and uses
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Page/Page column 11; sheet 7, (2008/06/13)
The invention relates to immunogenic glycopeptides derived from pathogenic microorganisms, which can be used for immunization and diagnosing infections dye to such pathogenic microorganisms and also to method for the selection and preparation thereof.
Sulfinyl hexose derivatives useful for glycosylation
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, (2008/06/13)
Hexose derivatives are described which facilitate control over the stereochemistry of the glycosyl bond formed in the course of a solid phase glycosylation reaction. Methods for their use are also described.
Carbohydrate Homologation by the Use of 2-(Trimethylsilyl)thiazole. Preparative Scale Synthesis of Rare Sugars: L-Gulose, L-Idose, and the Disaccharide Subunit of Bleomycin A2
Dondoni, Alessandro,Marra, Alberto,Massi, Alessandro
, p. 6261 - 6267 (2007/10/03)
The well established one-carbon homologation method of protected monosaccharides employing 2-(trimethylsilyl)thiazole (2-TST) as a formyl anion equivalent has been used for high yield and multigram scale synthesis of the title rare hexoses from L-xylose. Thus, L-gulose has been obtained by stereoselective anti-addition of 2-TST to aldehydo-L-xylose diacetonide followed by thiazole to formyl conversion of the resulting alcohol. The inversion of configuration at C-1 of this alcohol by an oxidation - reduction sequence prior to the aldehyde releasing from thiazole led to L-idose. The same alcohol was readily elaborated into 1,3,4,6-tetra-O-acetyl-L-gulopyranose whose highly stereoselective glycosidation coupling with 3-O-carbamoyl-2,4,6-tri-O-acetyl-α-D-mannosyl diethyl phosphate afforded the same peracetylated disaccharide subunit employed by Boger and Honda in the total synthesis of the antibiotic bleomycin A2.