502642-85-5Relevant articles and documents
Radiosynthesis of 18F-labeled D-allose
Yamamoto, Hiroyuki,Wada, Kenji,Toyohara, Jun,Tago, Tetsuro,Ibaraki, Masanobu,Kinoshita, Toshibumi,Yamamoto, Yuka,Nishiyama, Yoshihiro,Kudomi, Nobuyuki
, (2019)
Rare sugars are defined as monosaccharides that exist in nature but are only present in limited quantities. D-Allose is a rare sugar that has been reported to have some unique physiological effects. The present study describes suitable synthetic procedures for novel rare sugars of D-allose that are 18F-labeled at the C-3 and C-6 positions and the preparation of the appropriate labeling precursors. The goal is to facilitate in vivo, noninvasive positron emission tomography (PET) investigation of the behavior of rare sugar analogs of D-allose in organs. We found five precursors that were practical for labeling, three for 3-deoxy-3-[18F]fluoro-D-allose ([18F]3FDA) and two for 6-deoxy-6-[18F]fluoro-D-allose ([18F]6FDA). With manual operation synthesis, the highest radiochemical conversion rates were 75% for [18F]3FDA with a precursor of 1,2,4,6-tetra-O-acetyl-3-O-trifluoromethanesulfonyl-β-D-glucopyranose and 69% for [18F]6FDA with a precursor of 1,2,3,4-tetra-O-acetyl-6-O-trifluoromethanesulfonyl-β-D-allopyranose. Furthermore, the practical yields of [18F]3FDA and [18F]6FDA using an automated synthesizer were also investigated. Radiochemical yields of 67% and 49% were obtained for [18F]3FDA and [18F]6FDA, respectively, in an automated synthesizer. As basic assessment of stability for use in PET scanning, high performance liquid chromatography analysis showed no decomposition of [18F]3FDA and [18F]6FDA after up to 6 h in rabbit blood plasma.
Fluorinated Carbohydrates as Lectin Ligands: Simultaneous Screening of a Monosaccharide Library and Chemical Mapping by 19F NMR Spectroscopy
Martínez, J. Daniel,Manzano, Ana I.,Calvi?o, Eva,Diego, Ana De,Rodriguez De Francisco, Borja,Romanò, Cecilia,Oscarson, Stefan,Millet, Oscar,Gabius, Hans-Joachim,Jiménez-Barbero, Jesús,Ca?ada, Francisco J.
, p. 16072 - 16081 (2020/12/22)
Molecular recognition of carbohydrates is a key step in essential biological processes. Carbohydrate receptors can distinguish monosaccharides even if they only differ in a single aspect of the orientation of the hydroxyl groups or harbor subtle chemical
Anomeric Selectivity of Trehalose Transferase with Rare l -Sugars
Bento, Isabel,Hagedoorn, Peter-Leon,Hanefeld, Ulf,Jeffries, Cy M.,Laustsen, Jesper U.,Marsden, Stefan R.,Mestrom, Luuk,Svergun, Dmitri I.,Van Der Eijk, Hessel
, p. 8835 - 8839 (2020/09/18)
Retaining LeLoir glycosyltransferases catalyze the formation of glycosidic bonds between nucleotide sugar donors and carbohydrate acceptors. The anomeric selectivity of trehalose transferase from Thermoproteus uzoniensis was investigated for both d- and l-glycopyranose acceptors. The enzyme couples a wide range of carbohydrates, yielding trehalose analogues with conversion and enantioselectivity of >98%. The anomeric selectivity inverts from α,α-(1 → 1)-glycosidic bonds for d-glycopyranose acceptors to α,β-(1 → 1)-glycosidic bonds for l-glycopyranose acceptors, while (S)-selectivity was retained for both types of sugar acceptors. Comparison of protein crystal structures of trehalose transferase in complex with α,α-trehalose and an unnatural α,β-trehalose analogue highlighted the mechanistic rationale for the observed inversion of anomeric selectivity.
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.
CARRIER-FREE RADIOACTIVE HALOGEN LABELED DEOXYHALOGENO-D-ALLOSE, NON-RADIOACTIVE DEOXYFLUORO-D-ALLOSE, THEIR PRECURSOR, AND THEIR PRODUCTION METHOD
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Paragraph 0080-0082, (2018/04/03)
PROBLEM TO BE SOLVED: To provide new radioactive halogen labeled substances with a D-allose skeleton, a production method thereof, and the like. SOLUTION: A radioactive halogen labeled deoxyhalogeno-D-allose derivative is a compound represented by the general formula (1) or general formula (2) in the figure or a salt thereof. In the formulas (1) and (2), X is a halogen radioisotope such as 18F. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT
Synthesis method and application of sialylated TF antigen and its fluorination derivatives
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, (2018/07/07)
The invention discloses a synthesis method and an application of a sialylated TF antigen and its fluorination derivatives. The method includes the following steps: (1) chemically synthesizing fluorogalactose and fluorogalactosamine analogues; (2) chemically synthesizing a fluorinated TF antigen; and (3) synthesizing the sialylated TF antigen and its fluorination derivatives through an enzyme technology. The flexibility of a chemical synthesis technology is combined with the high regioselectivity and the high efficiency of the enzyme synthesis technology, so the enzymatic synthesis of the fluorosialylated TF antigen is achieved for the first time, and the disadvantages of many synthesis steps, poor stereoselectivity, low yield and use of a heavy metal salt in existing chemical synthesis ofthe fluorosialylated TF antigen are overcome. A fluorotumor-associated carbohydrate antigen has a higher stability than natural carbohydrate antigen, so the sialylated TF antigen and its fluorinationderivatives have a broad application prospect in the development of novel antitumor vaccines.
Probe sialidase substrate specificity using chemoenzymatically synthesized sialosides containing C9-modified sialic acid
Khedri, Zahra,Muthana, Musleh M.,Li, Yanhong,Muthana, Saddam M.,Yu, Hai,Cao, Hongzhi,Chen, Xi
supporting information; experimental part, p. 3357 - 3359 (2012/05/04)
A library of α2-3- and α2-6-linked sialyl galactosides containing C9-modified sialic acids was synthesized from C6-modified mannose derivatives using an efficient one-pot three-enzyme system. These sialosides were used in a high-throughput sialidase substrate specificity assay to elucidate the importance of C9-OH in sialidase recognition. The Royal Society of Chemistry 2012.
Fluorinated glycosyl amino acids for mucin-like glycopeptide antigen analogues
Wagner, Sarah,Mersch, Christian,Hoffmann-Roeder, Anja
supporting information; experimental part, p. 7319 - 7330 (2010/09/16)
The aberrant glycosylation profiles of mucin glycoproteins on epithelial tumour cells represent attractive target structures for the development of immunotherapy against cancer. Mucin-type glycopeptides have been successfully investigated as molecularly defined vaccine prototypes for triggering humoral immunity but are susceptible to rapid in vivo degradation. As a potential means to enhance the bioavailabilities of the antigenic structures, hydrolysis-resistant carbohydrate analogues with fluorine substituents at positions C6, C2′ and C6′ were synthesised and incorporated into the tandem repeat sequence of the mucin MUC1. The resulting pseudo-glycopeptides can be used to elucidate the effects of chemically modified antibody determinants on metabolic and immunological properties.
Developing an asymmetric, stereodivergent route to selected 6-deoxy-6-fluoro-hexoses
Caravano, Audrey,Field, Robert A.,Percy, Jonathan M.,Rinaudo, Giuseppe,Roig, Ricard,Singh, Kuldip
experimental part, p. 996 - 1008 (2009/05/30)
Free radical bromination and nucleophilic fluorination allows the conversion of methyl sorbate into the 6-fluoro analogue which undergoes sequential asymmetric dihydroxylation reactions. A range of 6-deoxy-6- fluorosugars were prepared by using different
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.
