A5085120673- Carbohydrate Chemistry and Synthesis
- Glycosylation and Glycoproteins Research
- Proteoglycans and glycosaminoglycans research
- Chemical Synthesis and Analysis
- Monoclonal and Polyclonal Antibodies Research
- vaccines and immunoinformatics approaches
- Synthesis of Organic Compounds
- Catalytic Cross-Coupling Reactions
- SARS-CoV-2 and COVID-19 Research
- Platelet Disorders and Treatments
- Enzyme Production and Characterization
- Bacteriophages and microbial interactions
- Phytochemical compounds biological activities
- Click Chemistry and Applications
- Fluorine in Organic Chemistry
- Catalytic C–H Functionalization Methods
- Bioactive Compounds and Antitumor Agents
- X-ray Diffraction in Crystallography
- Vanadium and Halogenation Chemistry
- Microbial Natural Products and Biosynthesis
- Crystallization and Solubility Studies
- Fibroblast Growth Factor Research
- Carbon dioxide utilization in catalysis
- Nanomaterials for catalytic reactions
Michigan State University
2014-2024
University of Chinese Academy of Sciences
2024
East China University of Science and Technology
2010-2012
Shanghai Institute of Organic Chemistry
2010-2012
Chinese Academy of Sciences
2010-2012
Kaempferol 3-O-(3'',6''-di-O-E-p-coumaroyl)-β-D-glucopyranoside (1), an optimal metabolite of Scots pine seedlings for protection deep-lying tissue against damaging UV-B, represents a typical acylated flavonol 3-O-glycoside. This compound was synthesized the first time via two approaches. The approach, starting with kaempferol, featured formation 3-O-glycosidic linkage glycosyl bromide under conventional PTC conditions. In second 5,7,4'-tri-O-benzyl-kaempferol readily prepared from...
Abstract Poly-β-(1–6)- N -acetylglucosamine (PNAG) is an important vaccine target, expressed on many pathogens. A critical hurdle in developing PNAG based that the impacts of number and position free amine vs -acetylation its antigenicity are not well understood. In this work, a divergent strategy developed to synthesize comprehensive library 32 pentasaccharides. This enables identification sequences with specific patterns amines as epitopes for vaccines against Staphylococcus aureus ( S. ),...
Due to the wide presence of carbohydrates in nature and their crucial roles numerous important biological processes, oligosaccharides have attracted a lot attention synthetic organic chemistry community. Many innovative methods been developed for oligosaccharide synthesis, among which pre‐activation‐based glycosylation is particularly noteworthy. Traditionally, reactions are carried out when glycosyl donor acceptor both present promoter added. In comparison, unique, where activated by...
Bikunin, a chondroitin sulfate (CS) proteoglycan clinically used to treat acute inflammation and sepsis, contains CS chain with more than 20 monosaccharide units. To understand the function of bikunin, synthesis long chains is needed. After exploring multiple glycosylation approaches protective group chemistry, we report herein successful generation longest date (24-mer) in an excellent overall yield on multi-mg scale. The anti-inflammatory activities both bikunin synthetic 24-mer were...
Abstract Despite the ubiquitous presence of proteoglycans in mammalian systems, methodologies to synthesize this class glycopeptides with homogeneous glycans are not well developed. Herein, we report first synthesis a glycosaminoglycan family glycopeptide containing two different heparan sulfate chains, namely extracellular domain syndecan‐3. With large size and tremendous structural complexity these molecules, multiple unexpected obstacles were encountered during synthesis, including high...
Attaching heparan sulfate glycan on a peptide backbone can modulate biological functions of the glycan.
Heparan sulfate (HS) plays important roles in many biological processes. The inherent complexity of naturally existing HS has severely hindered the thorough understanding their structure-activity relationship. To facilitate studies, a new strategy been developed to synthesize HS-like pseudo-hexasaccharide library, where disaccharides were linked "head-to-tail" fashion from reducing end disaccharide module non-reducing neighboring module. Combinatorial syntheses 27 pseudo-hexasaccharides...
Syndecan-1 chondroitin sulfate glycopeptide was synthesized for the first time using cassette approach. The sequence of glycosylation to form octasaccharide serine critical. successfully assembled via a 2+ (3 + 3) strategy followed by peptide chain elongation.
A glycopeptide bearing a bisecting glucosamine, rare N-glycan branch, and two Lewis<sup>X</sup>trisaccharides was synthesized for the first time.
The formation of an unprecedented 12-membered macrocyclic ketal through the long-range participation a levulinoyl group across glycosidic linkage was observed in glycosylation reactions. This finding indicated that stereodirecting is not limited to groups within glycan ring being activated, thus broadening scope remote glycosylation.
The immune system produces a diverse collection of antiglycan antibodies that are critical for host defense. At present, however, we know very little about the binding properties, origins, and sequences these because lack access to variety defined individual antibodies. To address this challenge, used glycan microarray with over 800 different components screen panel 516 human monoclonal had been randomly cloned from B-cell subsets originating healthy subjects. We obtained 26 antibodies, most...
Abstract Despite the ubiquitous presence of proteoglycans in mammalian systems, methodologies to synthesize this class glycopeptides with homogeneous glycans are not well developed. Herein, we report first synthesis a glycosaminoglycan family glycopeptide containing two different heparan sulfate chains, namely extracellular domain syndecan‐3. With large size and tremendous structural complexity these molecules, multiple unexpected obstacles were encountered during synthesis, including high...
Kaempferol 3-O-[2′′,3′′- and 2′′,4′′-di-O-(E)-p-coumaroyl]-α-l-rhamnopyranoside, two acylated flavonol 3-O-glycosides with potent inhibitory activity against methicillin-resistant Staphylococcus aureus, were synthesized for the first time, employing glycosyl o-cyclopropylethynylbenzoates as donors Ph3PAuNTf2 a catalyst construction of glycosidic linkages.
A successful synthesis of O-sulfated syndecan-1-like (Q23–E120) glyco-polypeptide was accomplished. The features the integration an carbohydrate-bearing glycopeptide cassette with efficient protein ligation strategies, overcoming acid lability carbohydrate sulfates as a major hurdle in solid-phase peptide synthesis. Crucial to is microwave-assisted Ag(I) ligation, which afforded product improved overall yield. This syndecan-1 longest prepared date.
Among many hurdles in synthesizing proteoglycan glycopeptides, one challenge is the incorporation of aspartic acid peptide backbone and sensitive O-sulfated glycan chains. To overcome this, a new strategy was developed utilizing homoserine as an precursor. The conversion to glycopeptide successfully accomplished by late stage oxidation using (2,2,6,6-tetramethyl-piperidin-1-yl)oxyl (TEMPO) bis(acetoxy)iodobenzene (BAIB). This first time that containing synthesized.
Kaempferol-5-O-α-L-rhamnopyranoside (1) and kaempferol-3,5-di-O-α-L-rhamnopyranoside (2) are representative flavonol 5-O-rhamnopyranoside.Because of the strong intramolecular H-bond, 5-O-glucosidic linkage could not be efficiently constructed via conventional glycosylation method.In this paper, a novel method was used which is gold(I)-catalyzed with glycosyl ortho-alkynylbenzoates as donor to achieve formation challenging kaempferol-5-O-glycosidic linkages, finally leading naturally...
More than 3 years into the global pandemic, severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) remains a significant threat to public health. Immunities acquired from infection or current vaccines fail provide long term protection against subsequent infections, mainly due their fast-waning nature and emergence of variants concerns (VOCs) such as Omicron. To overcome these limitations, SARS-CoV-2 Spike protein receptor binding domain (RBD)-based epitopes are investigated conjugates...
In the presence of Et3N and n-BuOH, efficient alkoxycarbonylation (hetero)aromatic bromides was achieved under atmospheric pressure carbon monoxide with in situ generated palladium/rac-BINAP as catalyst.
Abstract PdCl 2 /BINAP as the catalyst system allows efficient esterification of p‐substituted aromatic and heteroaromatic bromides with low CO pressure.