A5033959946- Carbohydrate Chemistry and Synthesis
- Glycosylation and Glycoproteins Research
- Chemical Synthesis and Analysis
- Monoclonal and Polyclonal Antibodies Research
- Fluorine in Organic Chemistry
- Enzyme Production and Characterization
- Sulfur-Based Synthesis Techniques
- Click Chemistry and Applications
- Synthetic Organic Chemistry Methods
- Natural product bioactivities and synthesis
- Galectins and Cancer Biology
- Immunotherapy and Immune Responses
- Chemical Synthesis and Reactions
- RNA and protein synthesis mechanisms
- Peptidase Inhibition and Analysis
- HIV Research and Treatment
- Legume Nitrogen Fixing Symbiosis
- Proteoglycans and glycosaminoglycans research
- Enzyme Catalysis and Immobilization
- Catalytic Cross-Coupling Reactions
- Pneumocystis jirovecii pneumonia detection and treatment
- Inorganic Fluorides and Related Compounds
- Polysaccharides and Plant Cell Walls
- Catalytic C–H Functionalization Methods
- Radical Photochemical Reactions
Peking University
2016-2025
Jiangxi Normal University
2015-2024
State Key Laboratory of Natural and Biomimetic Drugs
2010-2024
Nanjing University
2021
Lanzhou University
2015-2016
Center for Translational Molecular Medicine
2015-2016
University of Oxford
2009
University of Toledo
2004
Scripps Research Institute
1998-2001
Chinese University of Hong Kong
1996-1997
In an effort to develop a broadly applicable approach the facile one-pot synthesis of oligosaccharides, reactivity number p-methylphenyl thioglycoside (STol) donors which are either fully protected or have one hydroxyl group exposed has been quantitatively determined by HPLC. We characterized and quantified influence on structural effects different monosaccharide cores protecting groups each glycoside donor. addition, we established correlation between glycosyl donor chemical shift anomeric...
Abstract Carbohydrates are diverse bio-macromolecules with highly complex structures that involved in numerous biological processes. Well-defined carbohydrates obtained by chemical synthesis essential to the understanding of their functions. However, is greatly hampered its insufficient efficiency. So far, assembly long carbohydrate chains remains one most challenging tasks for synthetic chemists. Here we describe a efficient 92-mer polysaccharide preactivation-based one-pot glycosylation...
Straight to the point! Preactivation of a p-tolyl thioglycoside donor, followed by sequential addition thioglycosyl acceptors in one reaction flask allowed rapid syntheses oligosaccharides independent anomeric reactivities donors and (see scheme). This strategy greatly streamlines assembly oligosaccharides. Supporting information for this article is available on WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z460176_s.pdf or from author. Please note: The publisher not responsible...
Entry inhibitors are of particular importance in current efforts to develop a new generation anti-influenza virus drugs. Here we report certain pentacyclic triterpenes exhibiting conserved structure features and with vitro activity comparable even higher than that oseltamivir. Mechanistic studies indicated these lead triterpenoids bind tightly the viral envelope hemagglutinin (HA), disrupting interaction HA sialic acid receptor thus attachment viruses host cells. Docking suggest binding...
A stereoselective Koenigs-Knorr glycosylation reaction under the catalysis of urea is described. This method characterized by urea-mediated hydrogen-bond activation and subsequent with glycosyl chlorides or bromides. Excellent yields high anomeric selectivity can be achieved in most cases. Moreover, low α-stereoselectivity glycosylations observed when using perbenzylated glucosyl donors greatly improved addition tri-(2,4,6-trimethoxyphenyl)phosphine (TTMPP).
The assembly of an oligosaccharide library has been achieved in a practical and efficient manner employing one-pot sequential approach. With the help anomeric reactivity values thioglycosides, using thioglycoside (mono- or disaccharide) with one free hydroxyl group as acceptor donor coupled another fully protected thioglycoside, di- trisaccharide is selectively formed without self-condensation subsequently reacted situ anomerically inactive glycoside to form tri- tetrasaccharide high overall...
ADVERTISEMENT RETURN TO ISSUEPREVCommunicationNEXTAssembly of Oligosaccharide Libraries with a Designed Building Block and an Efficient Orthogonal Protection−Deprotection StrategyChi-Huey Wong, Xin-Shan Ye, Zhiyuan ZhangView Author Information Department Chemistry The Skaggs Institute for Chemical Biology Scripps Research 10550 North Torrey Pines Road, La Jolla, California 92037 Cite this: J. Am. Chem. Soc. 1998, 120, 28, 7137–7138Publication Date (Web):July 3, 1998Publication History...
Oxidative Heck-type C-glycosylations of glycals with various arylboronic acids using Pd(OAc)2 as catalyst in the presence oxidant were developed. The corresponding ketone, enol ether, and enone types C-glycosides predictably obtained benzoquinone (BQ), Cu(OAc)2/O2, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidants, respectively. This method provides a simple, mild, stereoselective synthesis aryl 2-deoxy-C-glycosides.
A monoselective synthesis of aryl-C-Δ1,2-glycosides from 1-iodoglycals via palladium-catalyzed ortho-C–H activation N-quinolyl benzamides has been developed. An amino acid derivative was used as a crucial ligand to improve the yield and monoselectivity coupling reaction. The utility this protocol demonstrated by concise key moieties some natural products.
We report a novel and highly stereoselective electro-2-deoxyglycosylation from glycals. This method features excellent stereoselectivity, scope, functional-group tolerance. process can also be applied to the modification of wide range natural products drugs. Furthermore, scalable synthesis glycosylated podophyllotoxin one-pot trisaccharide through iterative electroglycosylations were achieved.
The abnormal glycans expressed on the surface of tumor cells, known as tumor-associated carbohydrate antigens, increase chance to develop carbohydrate-based anticancer vaccines. However, antigens pose certain difficulties, and major drawback is their weak immunogenicity. To tackle this problem, numerous structurally modified STn were designed synthesized in work. These synthetic screened vitro by using competitive ELISA method, with positive response conjugated protein carrier for...
The Heck coupling of aryl iodides with pyranoid glycals using a catalytic amount Pd(OAc)2 to form C-glycosides has been achieved. reaction takes place smoothly in the presence Ag2CO3 and Cu(OAc)2 (or DMSO) acetonitrile. This arylation process, which occurs highly regio- stereo-selective manner, provides simple, mild, efficient approach synthesis 2-deoxy-C-glycopyranosides.
A glycosyl coupling reaction via photoinduced direct activation of thioglycosides and subsequent O-glycosylation in the absence photosensitizer was developed for first time. This underwent a selectively homolytic cleavage C–S bond to generate radical, which oxidized an oxacarbenium ion by Cu(OTf)2, sequential O-glycosylation. wide range glycosides were synthesized moderate excellent yield using sugars, amino acids, or cholesterol as acceptors.
A mild, efficient, and practical transformation for the direct C–H trifluoromethylation of glycals under visible light has been reported first time. This reaction employed fac-Ir3+(ppy)3 as photocatalyst, Umemoto’s reagent CF3 source, a household blue LED or sunlight source. Glycals bearing both electron-withdrawing -donating protective groups performed this smoothly. light-mediated was highlighted by biologically important Neu2en moiety.
A general approach to the synthesis of diverse heteroaryl-C-Δ1,2-glycosides has been developed by employing Pd(OAc)2/CuI cocatalyzed direct cross-coupling five-membered nitrogen heterocycles with 1-iodoglycals in a C–H activation manner. Using this method, 27 examples heteroaryl-C-Δ1,2-glycosides, containing indoles, thiazoles, benzothiazoles, imidazoles, benzimidazoles, and benzoxazoles as aglycones were obtained 43–99% yield.
Antibiotic resistance is one of the biggest threats to public health, and new antibacterial agents hence are in an urgent need combat infectious diseases caused by multidrug-resistant (MDR) pathogens. Utilizing dimerization strategy, we rationally designed efficiently synthesized a series small molecule dimeric lysine alkylamides as mimics AMPs. Evaluation these against panel Gram-positive Gram-negative bacteria including MDR strains was performed, broad-spectrum potent compound 3d...
A novel and efficient light-driven glycosylation strategy was developed with wide substrate scope/generality.
Abstract The photoinitiated intramolecular hydroetherification of alkenols has been used to form C−O bonds, but the intermolecular alkenes with alcohols remains an unsolved challenge. We herein report visible‐light‐promoted 2‐deoxyglycosylation glycals. glycosylation reaction was completed within 2 min in a high quantum yield ( ϕ =28.6). This method suitable for wide array substrates and displayed good yields excellent stereoselectivity. value this protocol further demonstrated by iterative...
Photochemical glycosylation has attracted considerable attention in carbohydrate chemistry. However, to the best of our knowledge, visible-light-promoted via photoactive glycosyl donor not been reported. In study, we report a photosensitizer-free visible-light-mediated approach using 2-glycosyloxy tropone as donor. This reaction proceeds at ambient temperature give wide range O-glycosides or oligosaccharides with yields up 99%. method is further applied stereoselective preparation various...