A5057100738- Carbohydrate Chemistry and Synthesis
- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Glycosylation and Glycoproteins Research
- Crystallography and molecular interactions
- Chemical Synthesis and Analysis
- Chemical Synthesis and Reactions
- Sulfur-Based Synthesis Techniques
- N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
- Oxidative Organic Chemistry Reactions
- Synthesis and Catalytic Reactions
- Catalytic C–H Functionalization Methods
- Synthetic Organic Chemistry Methods
- Catalytic Cross-Coupling Reactions
- Polyamine Metabolism and Applications
- Enzyme Production and Characterization
- Immune Cell Function and Interaction
- Legume Nitrogen Fixing Symbiosis
- Biochemical and Molecular Research
- Click Chemistry and Applications
- Enzyme Catalysis and Immobilization
- Bioactive Compounds and Antitumor Agents
- Natural product bioactivities and synthesis
- Catalytic Alkyne Reactions
- T-cell and B-cell Immunology
University College Dublin
2013-2024
East China Normal University
2024
Chemical Synthesis Lab
2014-2023
22q11 Ireland
2020
Chongqing University
2014-2016
Chinese Academy of Sciences
2000-2015
Zhejiang Normal University
2008-2015
Shanghai Institute of Organic Chemistry
1992-2015
Jinhua Academy of Agricultural Sciences
2014
Johns Hopkins University
2013
Increased understanding of the important roles that oligosaccharides and glycoconjugates play in biological processes has led to a demand for significant amounts these materials biological, medicinal, pharmacological studies. Therefore, tremendous effort been made develop new procedures synthesis glycosides, whereby main focus is often formation glycosidic bonds. Accordingly, quite few review articles have published over past years on glycoside synthesis; however, most are confined either...
Abstract Die wichtige Rolle , die Oligosaccharide und Glycokonjugate in biologischen Systemen spielen, erfordert immer neue vor allem größere Mengen dieser Moleküle. Wegen ihrer Heterogenität natürlichen Vorkommen wurden werden große Anstrengungen unternommen, um entscheidende glycosidische Bindung sowohl zwischen einzelnen Kohlenhydratresten als auch zu Aglyconen stereoselektiv hoher Ausbeute erzeugen. Es existieren nun verschiedene Methoden, effiziente Synthesen von strukturell definierten...
The synthesis, characterization, and biological evaluation of novel Ru(II)- Au(I)-N-heterocyclic carbenes is reported. NHC-ruthenium(II) complexes (1–6) were synthesized by reacting the appropriately substituted imidazolium bromides with Ag2O, forming NHC-silver bromide in situ followed transmetalation dimeric p-cymene ruthenium(II) dichloride. In an analogous manner NHC-gold(I) chloride (NHC-Au(I)Cl) 7–9 synthesized, utilizing dimethylsulfido gold(I) as transmetalating agent. ligand...
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Abstract In naturally occurring glycopeptides and glycoproteins the glycan residues generally possess N‐ O‐linkages to peptide backbone. Here we report synthesis of corresponding S ‐ linked by a convergent strategy provide compounds which should be quite stable glycosidases. To this end, peptides that contain β‐bromoalanine γ‐bromohomoalanine were generated either directly bromination serine homoserine residues, respectively, or standard ligation amino acids. 1‐Thiosugars O‐acetyl protected...
The first total synthesis of a thioglycoside analogue KRN7000, potential immunostimulant, is described. Two key intermediates are α-galactosyl thiol 4 and phytosphingosine derivative 5, which were both prepared from d-galactose.
Treatment of 1,6-anhydrosugars with commercially available bis(trimethylsilyl) sulfide in the presence trimethylsilyl triflate led to formation α-glycosyl thiols. All reactions were highly stereoselective and afforded thiols good excellent yields. By this procedure, a variety 1,6-anhydrosugars, differing their sugar units, glycosidic linkages, protecting group pattern, converted smoothly into corresponding thiols, which could be great utility thioglycoside chemistry. It is noteworthy that...
The anticancer drug candidate 1,3-dibenzyl-4,5-diphenyl-imidazol-2-ylidene gold(I) chloride (NHC-AuCl) and its 2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-1'-thiolate derivative (NHC-AuSR), which is a potential ligand for glucose transporters, were tested on the NCI 60 cancer cell panel in vitro. NHC-AuCl NHC-AuSR showed very good activity against wide range of human lines inclusive renal with similar average GI50 values 1.78 1.95 μM, respectively. This encouraged maximum tolerable dose...
Reaction of glycosylthiomethyl azides with amino acid and peptide derivatives containing aspartate glutamate thio acids gave the corresponding amides in excellent yields. Another type neoglycopeptides was obtained via reaction bromide cysteine homocysteine derivatives, thus affording S-(glycosylthiomethyl) peptides.
A new simple method for the synthesis of α-glycosyl thiols is described. Ring-opening 1,6-anhydrosugars with commercially available bis(trimethylsilyl)sulfide under action catalytic amounts TMSOTf smoothly afforded in very high yields and a stereospecific way.
The acid-catalyzed reaction of 1,2-anhydro-3,4,6-tri-O-benzyl-α-d-glucopyranose (7) as glycosyl donor with bis-trimethylsilyl sulfide acceptor affords the α-thiol. Hence, this sterically hindered S-nucleophile should provide O-glycosyl trichloroacetimidates donors that have nonparticipating groups at C-2, glycosylthiols thiol group in axial position. This was confirmed for various (4, 16–19) exception corresponding mannosyl (20). However, powerful participating C-2 (23–28) governed anomeric...
The influence of anomeric configuration upon thioglycoside donors remains relatively unexplored. Utilizing methodology developed for the stereoselective and high-yielding synthesis α-glycosyl thiols, a series α-thioglycosides were synthesized, their reactivity was compared to that β-counterparts. highly selective activation observed pairs containing 2-O-acyl moiety additional findings are reported. Application pair "superarmed" thioglycosides one-pot oligosaccharide system is also described,...
Investigation of direct S-glycosylation homocysteine and cysteine containing peptides with O-acetyl protected glycosyl halides led under two-phase conditions in the presence sodium carbonate as base to excellent results. Thus, from glucosyl bromide, galactosyl lactosyl sialyl chloride, N-Troc 2-amino-2-deoxyglucosyl bromide S-glycosylated dipeptides 15, 18−21, 23, 24, 26−29, respectively, were obtained yields. Alternatively, depending on solubility peptide moiety, mixtures DMF water could be...
We describe here the first synthesis of thioglycoside analogues maradolipid, based on a new procedure for 1-thiotrehalose developed recently in our laboratories. The challenging α,α-(1→1') thioglycosidic linkage was constructed by Schmidt's inverse very high yield and excellent stereoselectivity. Subsequent protecting group manipulation coupling with different fatty acids led smoothly to symmetrical unsymmetrical thiomaradolipids which would be value biological studies.
Thioperoxide (1) in combination with trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides a powerful thiophilic promoter system, capable of activating different thioglycosides. Both armed and disarmed thioglycosides were activated effectively the presence glycosyl acceptors, giving glycosidation products high to excellent yields. A plausible activation pathway was also proposed supported by isolating side-products trifluoromethylphenyl disulfide (CF3SSPh) alkene (42).
Ten novel N-heterocyclic carbene gold(I) complexes derived from lepidiline A (1,3-dibenzyl-4,5-dimethylimidazolium chloride) are reported here with full characterisation and biological testing. (1,3-Dibenzyl-4,5-diphenylimidazol-2-ylidene)gold(I) chloride (NHC*-AuCl) (1) was modified by substituting the for following: cyanide (2), dithiocarbamates (3–5), p-mercaptobenzoate derivatives (12–14) N-acetyl-l-cysteine (15–17). All were synthesised in good yields of 57–78%. Complexes 2, 12, 13, 14...
N-Benzylation of sulfonamides with both primary and secondary benzyl alcohols by employing boron trifluoride–diethyl ether complex under mild reaction conditions has been developed, which is an environmentally benign facile protocol for assembling a series in yields up to 83%. In this coupling reaction, the beneficial role water clarified detail through control experiments.