31077-88-0Relevant articles and documents
Addressing the Structural Complexity of Fluorinated Glucose Analogues: Insight into Lipophilicities and Solvation Effects
St-Gelais, Jacob,C?té, émilie,Lainé, Danny,Johnson, Paul A.,Giguère, Denis
supporting information, p. 13499 - 13506 (2020/10/02)
In this work, we synthesized all mono-, di-, and trifluorinated glucopyranose analogues at positions C-2, C-3, C-4, and C-6. This systematic investigation allowed us to perform direct comparison of 19F resonances of fluorinated glucose analogues and also to determine their lipophilicities. Compounds with a fluorine atom at C-6 are usually the most hydrophilic, whereas those with vicinal polyfluorinated motifs are the most lipophilic. Finally, the solvation energies of fluorinated glucose analogues were assessed for the first time by using density functional theory. This method allowed the log P prediction of fluoroglucose analogues, which was comparable to the C log P values obtained from various web-based programs.
Solid-Phase Synthesis of Fluorinated Analogues of Glycosyl 1-Phosphate Repeating Structures from Leishmania using the Phosphoramidite Method
Hara, Rintaro Iwata,Yaoita, Aya,Takeda, Katsuya,Ueki, Hiroaki,Ishii, Ayumu,Imoto, Hideyuki,Kobayashi, Satoshi,Sano, Michi,Noro, Mihoko,Sato, Kazuki,Wada, Takeshi
, p. 439 - 446 (2018/05/04)
Bacterial and protozoan sugar chains contain glycosyl 1-phosphate repeating structures; these repeating structures have been studied for vaccine development. The fluorinated analogues of [β-Gal-(1→4)-α-Man-(1→6)-P-]n, which are glycosyl 1-phosphate repeating structures found in Leishmania, were synthesised using the solid-phase phosphoramidite method. This method has been less extensively studied for the synthesis of glycosyl 1-phosphate units than H-phosphonate chemistry. A stepwise synthesis of a compound containing five such repeating units has been conducted using the phosphoramidite method herein, which is the longest glycosyl 1-phosphate structures to be chemically constructed in a stepwise manner.
Solid-supported reagents composed of a copolymer possessing 2-O-sulfonyl mannosides and phase-transfer catalysts for the synthesis of 2-fluoroglucose
Takeuchi, Ryota,Sakai, Yuki,Tanaka, Hiroshi,Takahashi, Takashi
supporting information, p. 5500 - 5503 (2015/11/18)
We described the synthesis of a solid-supported co-polymer possessing mannosides and phase-transfer catalysts and synthesis of 2-fluoroglucoside from it. We first prepared a soluble copolymer from two allene monomers possessing a precursor for the synthesis of 2-fluoroglycose and a crown ether. The copolymerization of the monomers via the π-ally nickel-catalyst smoothly proceeded at room temperature to provide a desired copolymer without decomposition of the sulfonate esters. The copolymer exhibited high reactivity towards fluorination in comparison with a conventional precursor. We next synthesized the solid-supported copolymer by using the solid-supported initiator attached with TentaGel resins. TentaGel enabled polymerization under stirring with stirring bar without decomposition. The solid-supported copolymer exhibited comparable reactivity towards fluorination in comparison with the soluble copolymer. In addition, it can be easily separated from the reaction vessel by filtration.
METHOD FOR PRODUCING 18F-LABELED COMPOUND AND HIGH MOLECULAR COMPOUND TO BE USED IN THE METHOD
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Page/Page column 22, (2013/02/28)
The present invention aims at solving the problems of conventional methods for producing an 18F-labeled compound, that is, the problem of purification of a compound in a liquid phase synthesis method and the problem of an insufficient yield due
d-Glucose- and d-mannose-based antimetabolites. Part 2. Facile synthesis of 2-deoxy-2-halo-d-glucoses and -d-mannoses
Fokt, Izabela,Szymanski, Slawomir,Skora, Stanislaw,Cybulski, Marcin,Madden, Timothy,Priebe, Waldemar
experimental part, p. 1464 - 1473 (2009/12/09)
Modified d-glucose and d-mannose analogs are potentially clinically useful metabolic inhibitors. Biological evaluation of 2-deoxy-2-halo analogs has been impaired by limited availability and lack of efficient methods for their preparation. We have develop
Sialidase substrate specificity studies using chemoenzymatically synthesized sialosides containing C5-modified sialic acids
Cao, Hongzhi,Li, Yanhong,Lau, Kam,Muthana, Saddam,Yu, Hai,Cheng, Jiansong,Chokhawala, Harshal A.,Sugiarto, Go,Zhang, Lei,Chen, Xi
scheme or table, p. 5137 - 5145 (2010/04/03)
para-Nitrophenol-tagged sialyl galactosides containing sialic acid derivatives in which the C5 hydroxyl group of sialic acids was systematically substituted with a hydrogen, a fluorine, a methoxyl or an azido group were successfully synthesized using an efficient chemoenzymatic approach. These compounds were used as valuable probes in high-throughput screening assays to study the importance of the C5 hydroxyl group of sialic acid in the recognition and the cleavage of sialoside substrates by bacterial sialidases.
Molecular recognition in the P2Y14 receptor: Probing the structurally permissive terminal sugar moiety of uridine-5′-diphosphoglucose
Ko, Hyojin,Das, Arijit,Carter, Rhonda L.,Fricks, Ingrid P.,Zhou, Yixing,Ivanov, Andrei A.,Melman, Artem,Joshi, Bhalchandra V.,Kovac, Pavol,Hajduch, Jan,Kirk, Kenneth L.,Harden, T. Kendall,Jacobson, Kenneth A.
experimental part, p. 5298 - 5311 (2009/12/04)
The P2Y14 receptor, a nucleotide signaling protein, is activated by uridine-5′-diphosphoglucose 1 and other uracil nucleotides. We have determined that the glucose moiety of 1 is the most structurally permissive region for designing analogues of this P2Y14 agonist. For example, the carboxylate group of uridine-5′-diphosphoglucuronic acid proved to be suitable for flexible substitution by chain extension through an amide linkage. Functionalized congeners containing terminal 2-acylaminoethylamides prepared by this strategy retained P2Y14 activity, and molecular modeling predicted close proximity of this chain to the second extracellular loop of the receptor. In addition, replacement of glucose with other sugars did not diminish P2Y14 potency. For example, the [5′′]ribose derivative had an EC50 of 0.24 μM. Selective monofluorination of the glucose moiety indicated a role for the 2′′- and 6′′-hydroxyl groups of 1 in receptor recognition. The β-glucoside was twofold less potent than the native α-isomer, but methylene replacement of the 1′′-oxygen abolished activity. Replacement of the ribose ring system with cyclopentyl or rigid bicyclo[3.1.0]hexane groups abolished activity. Uridine-5′-diphosphoglucose also activates the P2Y2 receptor, but the 2-thio analogue and several of the potent modified-glucose analogues were P2Y14-selective.
Studies on the reaction of D-glucal and its derivatives with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]Octane salts
Ortner,Albert,Weber,Dax
, p. 297 - 316 (2007/10/03)
The reaction of D-glucal and its derivatives with the electrophilic N-F-fluorination reagents F-TEDA tetrafluoroborate and triflate was studied by means of 19F NMR spectroscopy. In all cases mixtures of 2-deoxy-2-fluoro-D-gluco- and -D-mannopyranose derivatives were formed, the ratio of which was dependent on the nature of the O-protecting groups. Concerning the products arising from the direct addition of reagents across the double bond, the D-gluco-configured compounds (13-20) generally showed higher hydrolysis rates than their D-manno-counterparts (21-28). Product separation was only achieved when single anomers (e.g., 2,4-dinitrophenyl glycosides 29e/37e and disaccharidic fluorides 35d/43d) or per-O-acetates (e.g. 29f/37f) were formed.
A new method for the synthesis of fluoro-carbohydrates and glycosides using selectfluor
Burkart, Michael D.,Zhang, Zhiyuan,Hung, Shang-Cheng,Wong, Chi-Huey
, p. 11743 - 11746 (2007/10/03)
This paper describes a high-yield, one-step synthesis of 2-deoxy-2-fluoro sugars and their glycosides from glycals using the available electrophilic fluorination reagent 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2] octane bis(tetrafluoroborate) (Sel
Chemoenzymatic synthesis of fluorinated carbohydrates: 2-deoxy-2-fluoro-D-glucose and 5-deoxy-5-fluoro-manno-γ-lactol
Yan, Fengyang,Nguyen, Ba V.,York, Chentao,Hudlicky, Tomas
, p. 11541 - 11548 (2007/10/03)
Two fluorinated hexoses were prepared from optically active cis-diols 1, which were obtained by microbial oxidation of the corresponding halobenzenes with E. coli JM109 (pDTG 601). The stereochemistry of the products was controlled by careful introduction of fluorine onto the periphery of the cis-diols via opening of epoxides with tetrabutylphosphoniumfluoride dihydrofluoride (TBPF-DF). Oxidative cleavage of the cyclohexene skeleton followed by reductive cyclization led to the fluorinated hexoses.
