20880-92-6Relevant articles and documents
Preparation of enantiomerically pure fructose-derived 1,3-oxazin-2-one by INIR methodology and its application as a chiral auxiliary in some model asymmetric reactions
Banks, Malcolm R.,Cadogan,Gosney, Ian,Gould, Robert O.,Hodgson, Philip K. G.,McDougall, Douglas
, p. 9765 - 9784 (1998)
A newly developed fructose-based homochiral 1,3-oxazin-2-one reagent prepared via a regioselective and stereoselective intramolecular nitrene insertion reaction (INIR) exerts smooth stereocontrol resulting in high levels of asymmetric induction and chemical yield in various synthetic transformations including aldol, Diels-Alder cycloaddition and α-bromination reactions.
Structure-sweetness relationships for fructose analogs. Part I. Synthesis and evaluation of sweetness of 5-deoxy-D-threo-hexulose
Martin, Olivier R.,Korppi-Tommola, Sirkka-Liisa,Szarek, Walter A.
, p. 1857 - 1862 (1982)
5-Deoxy-D-threo-hexulose ("5-deoxyfructose", "5-deoxysorbose") has been prepared in six steps from D-fructose.The reaction of 2,3-O-isopropylidene-β-D-fructopyranose with sulfuryl chloride afforded exclusively 5-chloro-5-deoxy-2,3-O-isopropylidene-α-L-sorbopyranose in the key step. "5-Deoxyfructose" exists only in the 2C5(D) pyranoid form in solution, and was found to be much sweeter than L-sorbose and nearly as sweet as D-fructose.Comments on this unexpected sweetness result are given.
Synthesis and sensory characterization of novel umami-tasting glutamate glycoconjugates
Beksan, Ersan,Schieberle, Peter,Robert, Fabien,Blank, Imre,Fay, Laurent Bernard,Schlichtherle-Cerny, Hedwig,Hofmann, Homas
, p. 5428 - 5436 (2003)
Two glycoconjugates of glutamic acid, namely, the N-glycoside dipotassium N-(D-glucos-1-yl)-L-glutamate (1) and the corresponding Amadori compound N-(1-deoxy-D-fructos-1-yl)-L-glutamic acid (2), have been synthesized in yields of 35 and 52%, respectively, using new Maillard-mimetic approaches, and their chemical structures have unequivocally been elucidated by 1D- and 2D-NMR and MS experiments. Systematic sensory studies revealed that both glycoconjugates exhibit pronounced umami-like taste with recognition taste thresholds of 1-2 mmol/L, close to that of monosodium glutamate (MSG). Contrary to an aqueous solution of MSG, 1 does not show the sweetish and slightly soapy by-note, but evokes an intense umami taste. Aqueous solutions of 2 were described by the descriptors umami, seasoning, and bouillon-like. Added to a bouillon base, which did not contain any taste enhancers, both glycoconjugates imparted a distinct umami character similar to the control sample containing the same amount of MSG on a molar basis. To the best of our knowledge, these types of glycoconjugates in general and, in particular, N-glucosyl glutamate and N-deoxyfructosyl glutamate have never been reported as taste active compounds having umami-like properties. Therefore, 1 and 2 represent a new class of umami-type taste compounds showing properties similar to the umami reference compound MSG. Systematic 13C NMR measurements revealed that 1 was fairly stable in aqueous solutions under alkaline conditions (pH 8-10) as well as in dry form. However, it rapidly hydrolyzes in neutral and acidic solutions, giving rise to glucose and glutamate. In contrast, glycoconjugate 2 was observed to be rather stable in aqueous solution as well as in the presence of human saliva.
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Brady
, p. 35,39 (1970)
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Lipase-catalyzed esterification of steric hindered fructose derivative by continuous flow and batch conditions
Sutili, Felipe K.,Ruela, Halliny S.,Leite, Selma G.F.,Miranda, Leandro S. De M.,Leal, Ivana C.R.,De Souza, Rodrigo O.M.A.
, p. 37 - 42 (2013)
The lipase catalyzed sugar ester synthesis is an interesting strategy for producing biodegradable, non-ionic surfactants. The main disadvantage of this protocol is the long reaction time required for achieving moderated to good yields. Here, we report the esterification of steric hindered fructose derivative where important variables for batch conditions were identified by the use of a RSM protocol and then translated to the continuous flow regime with high conversions and short residence times.
A mild acetolysis procedure for the regioselective removal of isopropylidene in di-O-isopropylidene-protected pyranoside systems
Zhang, Pengfei,Ling, Chang-Chun
, p. 7 - 13 (2017)
A mild acetolysis method for the regioselective removal of isopropylidene group from di-O-isopropylidene-protected hexopyranosides is reported. O-Isopropylidene-protected intermediates play an important role in carbohydrate chemistry, as they are often found in commercially available furanosyl and pyranosyl materials, and some of them contain more than one O-isopropylidene groups. Methods that permit regioselective removal of O-isopropylidene groups are extremely valuable, as the number of steps in the total synthesis of complex oligosaccharides could be significantly decreased. Here we report that trifluoroacetic acid (TFA)/acetic anhydride (Ac2O) can be used to regioselectively convert one of the two O-isopropylidene groups to vicinal di-O-acetates in the di-O-isopropylidene-protected galacto- and fructo-pyranosyl systems, and the reagent is compatible with some common functionalities such as sulfonate esters, bromide, azide etc.
Synthesis and in?vitro Bioactivity Evaluation of New Galactose and Fructose Ester Derivatives of 5-Aminosalicylic Acid
Yousefi, Samira,Bayat, Saadi,Rahman, Mohd Basyaruddin Abdul,Ibrahim, Zalikha,Abdulmalek, Emilia
, (2017)
Inflammatory bowel disease (IBD) is the main risk factor for developing colorectal cancer which is common in patients of all ages. 5-Aminosalicylic acid (5-ASA), structurally related to the salicylates, is highly active in the treatment of IBD with minor side effects. In this study, the synthesis of galactose and fructose esters of 5-ASA was planned to evaluate the role of glycoconjugation on the bioactivity of the parent drug. The antibacterial activity of the new compounds were evaluated against two Gram-negative and two Gram-positive species of bacteria, with a notable effect observed against Staphylococcus aureus and Escherichia coli in comparisons with the 5-ASA. Cytotoxicity testing over HT-29 and 3T3 cell lines indicated that the toxicity of the new products against normal cells was significantly reduced compared with the original drug, whereas their activity against cancerous cells was slightly decreased. The anti-inflammatory activity test in RAW264.7 macrophage cells indicated that the inhibition of nitric oxide by both of the monosaccharide conjugated derivatives was slightly improved in comparison with the non-conjugated drug.
The first general protocol for N-monoalkylation of sulfamate esters: Benign synthesis of N-alkyl Topiramate (anticonvulsant drug) derivatives
Saeidian, Hamid,Abdoli, Morteza
, p. 463 - 470 (2015)
A novel protocol for the highly selective N-monoalkylation of the sulfamate ester moiety has been developed. This reaction proceeded efficiently using alkyl halides, benzyl halides and -halo ketones as the electrophile in the presence of KF-Al2O3 as a cost-effective and robust catalyst. This approach provides new access to N-monoalkylated Topiramate (anticonvulsant drug) derivatives which are potentially of great importance in medicinal chemistry.
Hydrate of 2,3:4,5-di-O-isopropylidene-β-D-arabino-hexos-2-ulo-2,6-pyranose as new crystalline reagent in the preparation of Amadori derived peptides
Stefanowicz, Piotr,Batorska, Joanna,Kijewska, Monika,Bartosz-Bechowski, Hubert,Szewczuk, Zbigniew,Lis, Tadeusz
, p. 28 - 33 (2010)
We established, that crystalline hydrate of 2,3:4,5-di-O-isopropylidene-β-D-arabino-hexos-2-ulo-2,6-pyranose is a new, convenient and stable reagent for solid phase synthesis of peptide derived Amadori products. The structure of the title compound was studied by X-ray analysis, NMR spectroscopy, and high resolution ESI-MS. The crystal structure indicated the existence of two symmetry-independent molecules that were not connected with hydrogen bonds. A comparison with previously reported 2,3:4,5-di-O-isopropylidene-β-D-fructopyranose revealed, that these two compounds are isostructural. Versita Warsaw and Springer-Verlag Berlin Heidelberg.
Crystal form of 2,3:4,5-di-O-(1-methylethylidene)-beta-D-fructopyranose chlorosulphate
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Paragraph 0073-0075, (2020/01/25)
The invention belongs to the technical field of pharmaceuticals, and particularly relates to a crystal form A of 2,3:4,5-di-O-(1-methylethylidene)-beta-D-fructopyranose chlorosulphate. The invention further relates to a preparation method of the 2,3:4,5-di-O-(1-methylethylidene)-beta-D-fructopyranose chlorosulphate and the purpose of the 2,3:4,5-di-O-(1-methylethylidene)-beta-D-fructopyranose chlorosulphate to preparation of Topiramate. The crystal form A of the prepared 2,3:4,5-di-O-(1-methylethylidene)-beta-D-fructopyranose chlorosulphate is high in purity, single-impurity 2,3:4,5-di-O-(1-methylethylidene)-beta-D-fructopyranose is smaller than 0.11%, the yield of the Topiramate prepared from the crystal form A of the 2,3:4,5-di-O-(1-methylethylidene)-beta-D-fructopyranose chlorosulphateis 92% or above, the HPLC purity is greater than 99.90%, the single-impurity 2,3:4,5-di-O-(1-methylethylidene)-beta-D-fructopyranose is smaller than 0.03%, and single impurities of a condensation compound are smaller than 0.05%.
Fructose modified breast cancer targeting lipid material, and preparation method and applications thereof
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Paragraph 0018, (2019/08/20)
The invention discloses a novel lipid material used for realizing breast cancer targeting medicine delivery and prolonging medicine acting time. According to the novel lipid material, endogenous cholesterol is subjected to modification, a joining chain is adopted, and connection with fructose with breast cancer targeting function is carried out, so that ligand molecules with breast cancer targeting function are prepared; the ligand molecules are adopted for modification of a lipid material, so that the affinity of the novel lipid material with acceptors is increased, better tumor targeting performance is achieved, and better breast cancer treatment effect is achieved. The novel lipid material can be used in different dosage forms including liposome, nanoparticle, and micelle, prepared Paclitaxel loaded liposome possesses obvious breast cancer targeting performance; and the application prospect is promising.