- Discovery of human Golgi β-galactosidase with no identified glycosidase using a QMC substrate design platform for exo-glycosidase
-
Post-translational modifications (PTMs) of proteins play important roles in the physiology of eukaryotes. In the PTMs, non-reversible glycosylations are classified as N-glycosylations and O-glycosylations, and are catalyzed by various glycosidases and glycosyltransferases. However, β-glycosidases are not known to play a role in N- and O-glycan processing, although both glycans provide partial structures as substrates for β-galactosidase and β-N-acetylglucosaminidase in the Golgi apparatus of human cells. We explored human Golgi β-galactosidase using fluorescent substrates based on a quinone methide cleavage (QMC) substrate design platform that was previously developed to image exo-type glycosidases in living cells. As a result, we discovered a novel Golgi β-galactosidase in human cells. It is possible to predict a novel and important function in glycan processing of this β-galactosidase, because various β-galactosyl linkages in N- and O-glycans exist in Golgi apparatus. In addition, these results show that the QMC platform is excellent for imaging exo-type glycosidases.
- Miura, Kazuki,Hakamata, Wataru,Tanaka, Ayako,Hirano, Takako,Nishio, Toshiyuki
-
-
Read Online
- Exploring the Condensation Reaction between Aromatic Nitriles and Amino Thiols To Optimize In Situ Nanoparticle Formation for the Imaging of Proteases and Glycosidases in Cells
-
The condensation reaction between 6-hydroxy-2-cyanobenzothiazole (CBT) and cysteine has been shown for various applications such as site-specific protein labelling and in vivo cancer imaging. This report further expands the substrate scope of this reaction by varying the substituents on aromatic nitriles and amino thiols and testing their reactivity and ability to form nanoparticles for cell imaging. The structure–activity relationship study leads to the identification of the minimum structural requirement for the macrocyclization and assembly process in forming nanoparticles. One of the scaffolds made of 2-pyrimidinecarbonitrile and cysteine joined by a benzyl linker was applied to design fluorescent probes for imaging caspase-3/7 and β-galactosidase activity in live cells. These results demonstrate the generality of this system for imaging hydrolytic enzymes.
- Chen, Min,Chen, Zixin,Cheng, Yunfeng,Kowada, Toshiyuki,Rao, Jianghong,Xie, Jinghang,Zheng, Xianchuang
-
-
Read Online
- Identification of a novel glycan processing enzyme with exo-acting β-allosidase activity in the Golgi apparatus using a new platform for the synthesis of fluorescent substrates
-
The majority of eukaryotic proteins undergo post-translational modifications (PTMs) involving the attachment of complex glycans, predominantly through N-glycosylation and O-glycosylation. PTMs play important roles in virtually all cellular processes, and aberrant regulation of protein glycosylation and glycan processing has been implicated in various diseases. However, glycan processing on proteins in various cellular contexts has not been visualized. We had previously developed a quinone methide cleavage (QMC) platform for enhanced substrate design. This platform was applied here to screen for novel glycan-processing enzymes. We designed and synthesized fluorescent substrates with β-allopyranoside residues using the QMC platform. When applied in cell-based assays, the fluorescent substrates allowed rapid and clear visualization of β-allosidase activity in the Golgi apparatus of human cultured cells. The QMC platform will likely find broad applications in visualizing the activities of glycan processing enzymes in living cells and in studying PTMs.
- Hakamata, Wataru,Miura, Kazuki,Hirano, Takako,Nishio, Toshiyuki
-
-
Read Online
- Highly chemoselective hydrogenation of active benzaldehydes to benzyl alcohols catalyzed by bimetallic nanoparticles
-
By using novel Pd/Ni bimetallic nanoparticles as a catalyst, the active benzaldehydes were hydrogenated to the corresponding benzyl alcohols as unique products in practical quantitative yields. The undesired catalytic hydrogenolysis of the benzyl alcohol was inhibited completely. By using this hydrogenation as a key step, the total synthesis of the natural product gastrodin was achieved with less total steps and a higher total yield.
- Liu, Chulong,Bao, Hailin,Wang, Dingsheng,Wang, Xinyan,Li, Yadong,Hu, Yuefei
-
-
Read Online
- Fluorescent probe for rapidly detecting β - galactosidase and preparation method and application thereof
-
The invention relates to a fluorescent probe for rapidly detecting β - galactosidase and a preparation method and application thereof. The fluorescent probe for rapidly detecting β - galactosidase has a chemical structural formula as shown in (I). The nea
- -
-
Paragraph 0047; 0051-0052; 0054
(2021/10/27)
-
- A General Approach to Enzyme-Responsive Liposomes
-
Liposomes are effective nanocarriers due to their ability to deliver encapsulated drugs to diseased cells. Nevertheless, liposome delivery would be improved by enhancing the ability to control the release of contents at the target site. While various stimuli have been explored for triggering liposome release, enzymes provide excellent targets due to their common overexpression in diseased cells. We present a general approach to enzyme-responsive liposomes exploiting targets that are commonly aberrant in disease, including esterases, phosphatases, and β-galactosidases. Responsive lipids correlating with each enzyme family were designed and synthesized bearing an enzyme substrate moiety attached via a self-immolating linker to a non-bilayer lipid scaffold, such that enzymatic hydrolysis triggers lipid decomposition to disrupt membrane integrity and release contents. Liposome dye leakage assays demonstrated that each enzyme-responsive liposome yielded significant content release upon enzymatic treatment compared to minimal release in controls. Results also showed that fine-tuning liposome composition was critical for controlling release. DLS analysis showed particle size increases in the cases of esterase- and β-galactosidase-responsive lipids, supporting alterations to membrane properties. These results showcase an effective modular strategy that can be tailored to target different enzymes, providing a promising new avenue for advancing liposomal drug delivery.
- Lou, Jinchao,Best, Michael D.
-
p. 8597 - 8607
(2020/07/04)
-
- COMPOUNDS COMPRISING CLEAVABLE LINKER AND USES THEREOF
-
Provided are a compound including a cleavable linker, a use thereof, and an intermediate compound for preparing the same, and more particularly, the compound including a cleavable linker of the present invention may include an active agent (for example, a drug, a toxin, a ligand, a probe for detection, etc.) having a specific function or activity, a SO2 functional group which is capable of selectively releasing the active agent, and a functional group which triggers a chemical reaction, a physicochemical reaction and/or a biological reaction by external stimulation, and may further include a ligand (for example, oligopeptide, polypeptide, antibody, etc.) having binding specificity for a desired target receptor.
- -
-
Page/Page column 189
(2020/07/21)
-
- Neuroprotective activity of different monosaccharide-modified gastrodin analogs
-
Gastrodin is a very important and well-known bioactive glycoside compound in Chinese medicine. It is also known as a drug with neuroprotective function. Here, a practical diversified synthesis of a series of gastrodin analogs was reported, which involved four-step procedures consisting of bromination, oxidation, etherification, and reduction. Various gastrodin analogs were obtained in good yields. The compound 4c in this study has a good neuroprotective function: it can significantly downregulate tumor necrosis factor-α and inducible nitric oxide synthase protein levels. The results of this study can provide a research basis for the development of neuroprotective drugs.
- Xu, Kun-Lun,Yu, Lan
-
p. 1263 - 1269
(2020/01/21)
-
- CASPASE-3-TRIGGERED MOLECULAR SELF-ASSEMBLING PET PROBES AND USES THEREOF
-
Embodiments of the synthesis, radiolabeling and biological applications of an activatable tracer that undergoes intramolecular cyclization and aggregation upon activation by cleavage of a blocking moiety are provided. The probes of the disclosure allow for target-controlled self-assembly of small molecules in living subjects for imaging and drug delivery. The aggregated nanoprobes of the disclosure may be detectable optically, by PET detection, magnetic resonance imaging, and the like depending on the detectable reporter attached to the nanoprobe.
- -
-
Page/Page column 0126; 0355
(2020/03/28)
-
- Cyano vinylene derivative fluorescent dye as well as preparation method and application thereof
-
The invention relates to a cyanovinylene derivative fluorescent dye as well as a preparation method and application thereof, and discloses a compound represented by a structural general formula (I), and the compound R1 is independently selected from H, NH2, OH, CN, CH3, COOH, SO3H, F, Cl, Br or NO2; R2 is a group described in the specification. The compound probe molecule provided by the inventioncan realize quantitative detection of beta-Gal in a buffer solution test system, is not interfered by other proteases, biological mercaptan, active oxygen and common cations, and is successfully applied to in-situ detection of beta-Gal in biological cells of SKOV3 cells.
- -
-
Paragraph 0015; 0017
(2020/05/05)
-
- A Novel Ratiometric Fluorescent Probe for Highly Sensitive and Selective Detection of β-Galactosidase in Living Cells
-
β-Galactosidase, a glycoside hydrolase enzyme, has been proved to be an important biomarker of cell senescence and primary ovarian cancer. Effective detection of β-galactosidase has attracted wide attention. Herein, one ratiometric fluorescent probe has been successfully synthesized for detecting the β-galactosidase in living cells. The as-prepared probe exhibits two emission peaks at 490 nm and 530 nm, respectively, and the ratio of fluorescence intensities from the two emission peaks could be utilized to monitor the β-galactosidase. This present ratiometric fluorescent probe is, therefore, very promising for effective, sensitive, and selective detection of the β-galactosidase in living cells.
- Chen, Min,Mu, Lixuan,Cao, Xingxing,She, Guangwei,Shi, Wensheng
-
p. 330 - 336
(2019/03/07)
-
- DUAL PROTECTED PRO-COELENTERAZINE SUBSTRATES
-
Described are coelenterazine analogues, methods for making the analogues, kits comprising the analogues, and methods of using the compounds for the detection of luminescence in luciferase-based assays.
- -
-
-
- Gastrodine drug and its composition and use thereof
-
The invention relates to a gastrodin medicine, and a composition and a use thereof, and also relates to a gastrodin derivative, and a preparation method and a use thereof. The gastrodin derivative has good storage stability, and is suitable for preparing medicines for increasing the cerebral blood flow, alleviating the cerebral vasospasm, calming, sleeping, easing pains, and treating or preventing Alzheimer's syndrome.
- -
-
Paragraph 0072; 0073; 0074
(2018/09/20)
-
- ANTIMICROBIAL COMPOUNDS AND USES THEREOF
-
The present invention generally relates to a class of antimicrobial compounds, to compositions containing said compounds and to the use of said compounds for medical and non-medical purposes. More specifically, the present invention relates to antimicrobial compounds capable of changing microbiota composition and function by selectively inhibiting distinct microbial species.
- -
-
Paragraph 00158; 00159
(2018/08/12)
-
- Combretastatin A4-β-Galactosyl Conjugates for Ovarian Cancer Prodrug Monotherapy
-
Chemotherapy for ovarian cancer often causes severe side effects. As candidates for combretastatin A4 (CA4) prodrug for ovarian cancer prodrug monotherapy (PMT), we designed and synthesized two β-galactose-conjugated CA4s (CA4-βGals), CA4-βGal-1 and CA4-βGal-2. CA4 was liberated from CA4-βGals by β-galactosidase, an enzyme more strongly expressed in ovarian cancer cells than normal cells. CA4-βGal-2, which has a self-immolative benzyl linker between CA4 and the β-galactose moiety, was more cytotoxic to ovarian cancer cell lines than CA4-βGal-1 without a linker. Therefore, CA4-βGal-2 can serve as a platform for the design and manufacture of prodrugs for ovarian cancer PMT.
- Doura, Tomohiro,Takahashi, Kazuaki,Ogra, Yasumitsu,Suzuki, Noriyuki
-
supporting information
p. 211 - 214
(2017/03/08)
-
- Ratiometric electrochemical detection of β-galactosidase
-
A novel ferrocene-based substrate for the ratiometric electrochemical detection of β-galactosidase was designed and synthesised. It was demonstrated to be an excellent electrochemical substrate for β-Gal detection with sensitivity as low as 0.1 U mL-1.
- Spring, Sam A.,Goggins, Sean,Frost, Christopher G.
-
supporting information
p. 7122 - 7126
(2017/09/07)
-
- Synthesis method of gastrodin
-
The invention discloses a synthesis method of gastrodin. The synthesis method of the gastrodin comprises the following steps: putting 4-formylphenyl-2,3,4,6-tetra-0-acetyl-beta-D-glucopyranoside and a reducing agent into a solvent, and conducting reaction at 0 to 30 DEG C for 0 to 3 hours; after complete reaction, adding water and performing quenching reaction; separating and taking an organic phase, concentrating the organic phase under the vacuum condition, and adding methanol in amount which is 2 to 5 times that of the organic phase; adding organic amine, performing refluxing reaction and performing alcoholysis; after complete reaction, adding activated carbon to decolor, filtering, concentrating, crystallizing and drying. By adoption of the synthesis method provided by the invention, the processes of the production process are reduced, and the method is safe, simple and convenient in operation, low in cost, low in pollution and suitable for large-scale production; furthermore, the prepared gastrodin product has stable quality and the purity is 99.9 percent or higher.
- -
-
Paragraph 0031; 0032; 0033; 0034
(2017/07/19)
-
- A high-purity, high-stability Gastrodin semi-synthetic method
-
The invention discloses a semi-synthesis method for high-purity and high-stability gastrodin. The semi-synthesis method comprises the following steps: carrying out a reduction reaction by taking tetraacethyl as a raw material; concentrating and adding a suitable amount of water into concentrated liquid; filtering and drying to obtain acethyl gastrodin; recycling a filtering solution which is used as a mother solution a; adding an alcohol solvent into the acethyl gastrodin to carry out a reflowing reaction, and concentrating; repeatedly reflowing and concentrating to obtain a concentrated solution; adding a non-polar solvent and filtering; drying solids to obtain a gastrodin rough product; recycling a filtering solution which is used as a mother solution b; adding alcohol and/or an ester solvent into the rough product of gastrodin; heating and completely dissolving; filtering and separating out crystals to obtain a refined product of gastrodin; recycling a filtering solution which is used as a mother solution c; mixing the mother solution b and the mother solution c; filtering and drying to obtain the rough product of gastrodin; and refining to obtain the refined product of gastrodin. The acethyl gastrodin prepared by the semi-synthesis method disclosed by the invention is stable, can be directly used as a crude drug, and can also be used as an intermediate to synthesize the high-purity gastrodin; the semi-synthesis method for the high-purity and high-stability gastrodin is very good for meeting the clinical demands on gastrodin and acethyl gastrodin.
- -
-
Page/Page column 8; 12
(2017/05/13)
-
- Gastrodin Gastrodin and method for the preparation of intermediates for the synthesis of
-
The invention discloses a method for preparing a gastrodin intermediate compound III. The method comprises the following steps: (1) reducing an initial raw material compound I through hydrogen, and obtaining a compound II; (2) reacting the compound II with an acetylation reagent, and obtaining a crude product of a compound III; and (3) recrystallizing the compound III obtained in the step (2), and obtaining a crude product of the compound III. In addition, the invention also provides a method for synthesizing gastrodin. The compound III prepared by the method provided in the invention is easy to recrystallize and high in purity, and a high-purity gastrodin finished product can be obtained.
- -
-
Paragraph 0079-0080
(2017/05/23)
-
- Helicid analogues for treating depression
-
The invention discloses helicid analogues for treating depression and relates to helicid derivatives such as 4-hydroxymethyl-beta-D-allopyranoside and 4-carboxylphenyl-beta-D-allopyranoside and their medicinal salts, esters and solvates. The helicid deriv
- -
-
Paragraph 0016; 0018
(2016/10/10)
-
- First and efficient synthesis of 4-[((3,4-dihydroxybenzoyl)-oxy)methyl]phenyl β-D-glucopyranoside, an antioxidant from Origanum vulgare
-
4-[((3,4-Dihydroxybenzoyl)oxy)methyl]phenyl β-D-glucopyranoside (DBPG, 1), a polyphenolic glycoside previously isolated from oregano (Origanum vulgare L.) in 0.08 % isolated yield, was synthesized in five chemical steps with 41.4 % overall yield. First, 4-(hydroxymethyl)phenyl ?-D-glucopyranoside 2,3,4,6-tetraacetate (4) was obtained in 53.2 % yield by selective glycosylation of 4-hydroxybenzyl alcohol (3) with 2,3,4,6-tetra-O-acetyl-a-D- -glucopyranosyl bromide (2) in a mixture of chlorobenzene and aqueous CsOH using triethylbenzylammonium chloride (TEBAC) as a phase transfer catalyst. Then, this product was esterified with 3,4-diacetoxybenzoyl chloride (7) to generate 4-[((3,4-diacetoxybenzoyl)oxy)methyl]phenyl ?-D-glucopyranoside 2,3,4,6-tetraacetate (8) in 95 % yield. Finally, selectively global deacetylation of 8 was performed in a mixture of dibutyltin oxide and methanol under reflux to afford 1 in 94.8 % yield.
- Li, Yu-Wen,Ma, Cui-Li
-
-
- Improved synthesis of gastrodin, a bioactive component of a traditional chinese medicine
-
Highly practical, four-step synthesis of gastrodin was developed using penta- O-acetyl-β-D-glucopyranose and p-cresol as glycosyl donor and glycosyl acceptor, respectively, in 58.1% overall yield. As the initial step, the penta-O-acetyl-β-D-glucopyranose was treated with p-cresol in the presence of BF3 ?Et2O as catalyst to generate 4-methylphenyl 2,3,4,6-tetra-O-acetyl-β-D- -glucopyranoside in 76.3% yield. Further, this product was subjected to radical bromination with N-bromosuccinimide (NBS) to provide 4-(bromomethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside in 91% yield. Subsequently, reaction of 4-(bromomethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside with a solution of acetone and saturated aqueous sodium bicarbonate led to 4-(hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside in 93% yield. Finally, global deprotection of 4-(hydroxymethyl)phenyl 2,3,4,6-tetra-O- -acetyl-β- D-glucopyranoside under Zemplen conditions furnished gastrodin in 90% yield. Compared to the previously reported methods, this protocol has the advantages of operational simplicity, chromatography-free separation, high overall yield, inexpensive and common reagents as well as less waste pollutants, rendering it an alternative suitable for industrial production.
- Li, Yu-Wen,Ma, Cui-Li
-
p. 1205 - 1212
(2015/01/30)
-
- ELECTROCHEMICAL METHODS AND COMPOUNDS FOR THE DETECTION OF ENZYMES
-
Disclosed are compositions and methods for the electrochemical detection of enzymes, such as enzymes that are indicative of disease, disorders, or pathogens, such as viruses, bacteria, and fungi, or other disorders. These methods can be used in point-of- care diagnostic assays for the detection of disease, disorder, or pathogen (e.g., to identify the strain of pathogen infecting a patient in a healthcare setting). The electrochemical methods described herein can also be used to assess the susceptibility of a pathogen to an antipathogen drug. Also provided are probes suitable for use in conjunction with the methods described herein.
- -
-
Page/Page column 53; 54
(2016/04/26)
-
- Molecular interactions between Barley and Oat β-glucans and phenolic derivatives
-
Equilibrium dialysis, molecular modeling, and multivariate data analysis were used to investigate the nature of the molecular interactions between 21 vanillin-inspired phenolic derivatives, 4 bile salts, and 2 commercially available β-glucan preparations, Glucagel and PromOat, from barley and oats. The two β-glucan products showed very similar binding properties. It was demonstrated that the two β-glucan products are able to absorb most phenolic derivatives at a level corresponding to the absorption of bile salts. Glucosides of the phenolic compounds showed poor or no absorption. The four phenolic derivatives that showed strongest retention in the dialysis assay shared the presence of a hydroxyl group in para-position to a CHO group. However, other compounds with the same structural feature but possessing a different set of additional functional groups showed less retention. Principal component analysis (PCA) and partial least-squares regression (PLS) calculations using a multitude of diverse descriptors related to electronic, geometrical, constitutional, hybrid, and topological features of the phenolic compounds showed a marked distinction between aglycon, glucosides, and bile salt retention. These analyses did not offer additional information with respect to the mode of interaction of the individual phenolics with the β-glucans. When the barley β-glucan was subjected to enzyme degradation, the ability to bind some but not all of the phenolic derivatives was lost. It is concluded that the binding must be dependent on multiple characteristics that are not captured by a single molecular descriptor.
- Simonsen, Henrik Toft,Nielsen, Mette S.,Christensen, Niels J.,Christensen, Ulla,Cour, Thomas V. La,Motawia, Mohammed Saddik,Jespersen, Birthe P.M.,Engelsen, Soren B.,Moller, Birger Lindberg
-
experimental part
p. 2056 - 2064
(2010/07/02)
-
- Detection of enzymatic activity by PARACEST MRI: A general approach to target a large variety of enzymes
-
(Chemical Equation Presented) Perfect timing: A "smart" pro-PARACEST agent has been designed to detect β-galactosidase activity. Upon enzymatic attack, the self-immolative benzyloxycarbamate linker bearing the enzyme-specific substrate is cleaved and yiel
- Chauvin, Thomas,Durand, Philippe,Bernier, Michele,Meudal, Herve,Doan, Bich-Thuy,Noury, Fanny,Badet, Bernard,Beloeil, Jean-Claude,Toth, Eva
-
supporting information; scheme or table
p. 4370 - 4372
(2009/02/08)
-
- FEEDBACK PRODRUG
-
Compounds and methods for use in selectively inhibiting a lytic enzyme based on feedback inhibition. The conjugated compound serves as a substrate for a lytic enzyme. Cleavage of the conjugated compound by the lytic enzyme releases an inhibitor of the enz
- -
-
Page/Page column 20
(2008/06/13)
-
- Selective inhibition of glycosidases by feedback prodrugs
-
(Figure Presented) In the loop: A novel concept for the selective inhibition of glycosidases has been developed whereby a glycosidase inhibitor is released by glycosidase-mediated hydrolysis of a prodrug, which subsequently inhibits the glycosidase that i
- Guo, Jun,Asong, Jinkeng,Boons, Geert-Jan
-
p. 5345 - 5348
(2007/10/03)
-
- Studies on the synthesis and antiproliferative activities of 13-cis-retinoyl sugar derivatives
-
New retinoyl sugar derivatives of 13-cis-retinoic acid were synthesized in three ways in this paper in order to enhance pharmacal effects, especially antiproliferative activities of 13-cis-retinoic acid. Their structures were confirmed by IR, 1H-NMR, 13C-NMR, and MS spectra and their antiproliferative activities were determined in vitro using human cancer lines. Results showed that some compounds possessed potential antitumor activities. Copyright Taylor & Francis Group, LLC.
- Xiang, Jian-Nan,Jiang, Li-Hui,Chen, Chao-Yue,Fu, Zhi-Ying,Duan, Jun-Fei,He, Xiao-Xiao,Wang, Ke-Min
-
p. 595 - 614
(2007/10/03)
-
- Structure and reactivity of glycosides: IV. Koenigs-Knorr synthesis of aryl β-D-glucopyranosides using phase-transfer catalysts
-
A series of acetylated aryl β-D-glucopyranosides were prepared in 12-63% yields from tetra-O-acetyl-α-D-glycopyranosyl bromide and phenols containing acyl, formyl, and hydroxy substituents, and also from sterically hindered phenols in the two-phase system chloroform-aqueous alkali in the presence of triethylbenzylammonium chloride. Hydroxyethylated sucrose and dibenzo-18-crown-6 do not behave as phase-transfer catalysts in glycosylation of phenols. 2001 MAIK "Nauka/Interperiodica".
- Pavlov,Sokolov,Zakharov
-
p. 1811 - 1814
(2007/10/03)
-
- A β-galactoside phosphoramide mustard prodrug for use in conjunction with gene-directed enzyme prodrug therapy
-
4-(β-D-Galactopyranosyl)benzyl N,N,N',N'-tetrakis(2- chloroethyl)phosphorodiamidate 1 was facilely biotransformed to the alkylating antitumor agent, N,N,N',N'-tetrakis(2-chloroethyl) phosphorodiamidic acid, 4, when incubated with E. coli β-galactosidase, and therefore has potential for use in conjunction with gene-directed enzyme prodrug therapy.
- Ghosh, Ajit K.,Khan, Saeed,Farquhar, David
-
p. 2527 - 2528
(2007/10/03)
-
- Glycosylated prodrugs, their method of preparation and their uses
-
Glycosylated prodrugs, a preparation method therefor, and their use with tumor-specific immunoenzymatic conjugates for the treatment of cancer, are described. These anthracycline prodrugs have formula (I). STR1
- -
-
-
- SYNTHESIS OF FLUORINE-CONTAINING NATURAL GASTRODIN AND ITS ANALOGUES
-
Reactions of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (2) with p-hydroxybenzaldehyde, trifluoromethyl and fluoro substituted aniline and 2-amino-6-fluorobenzoic acid gave 1-O-(p-formylphenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (3), 1-N-(m-trifluoromethylphenylamino)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4a), 1-N-(2-carboxyl-3-fluorophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4b) and 1-N-(p-fluorophenyl)-N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4c) respectively. 1-O-(perfluoro-2-propoxypropionyl)-O-benzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (7) and 1-O-(m-trifluoromethylphenylaminobenzylidene)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (8) were also prepared in subsequent reactions.Conversion of the acetyl group to the hydroxyl group yielded the corresponding deprotected product.The compounds formed have been characterized by analysis, IR, 1H and 19F NMR and mass spectroscopy.The influence of phase-transfer catalysts on the reactions is discussed.
- Lin, Yong-Da,Liang, Yu-Da,Liang, Shi-Gin,Zhang, Shi-Xiang,Chi, Ching-Sung
-
p. 367 - 374
(2007/10/02)
-
- Glycosidation catalust and process for preparing glycoside derivatives
-
Disclosed are a glycosidation catalyst comprising at least one of heteropoly acids represented by the formula wherein X is P, As, Si or Ge, M is at least one species selected from the group consisting of Mo, W and V, a is 3 4 or 6, b is an integer of
- -
-
-
- A New Antioxidative Glucoside Isolated from Oregano (Origanum vulgare L.)
-
A new antioxidative glucoside (1a) was isolated from the leaves of oregano (Origanum vulgare L.), one of the herbal species belonging to the Family Labiatae.The structure of 1a was determined as 4-(3,4-dihydroxybenzoyloxymethyl)phenyl-β-D-glucopyranoside, on the basis of chemical and spectroscopic evidence.In addition, the structure was confirmed by synthesizing its acetyl derivative (1b).
- Nakatani, Nobuji,Kikuzaki, Hiroe
-
p. 2727 - 2732
(2007/10/02)
-