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Novel glycosyl donors possessing several para-substituted O-aryl protecting groups that are introduced using diaryliodonium triflate have been developed, and their glycosylation stereoselectivity was evaluated. β-Selective glycosylation was achieved using thioglycosides protected by 4-nitrophenyl (NP) groups. Analysis of the stereoselectivity of several glycosyl donors indicated that β-glycosides are obtained through an SN2-like displacement from the corresponding α-glycosyl triflate. The NP group can be removed by reduction of the nitro group and acylation, followed by ammonium hexanitratocerate (IV) (CAN) oxidation.
This article was published in the following journal.
Name: Chemistry, an Asian journal
Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported in the literature over many decades and so far still mainly relies on trial and error. Herein, we descri...
Herein, we reported on a highly efficient glycosylation reaction comprises two chronological meticulously-designed catalytic cycles: 1) rhodium-catalyzed formation of sulfonium ylide; 2) Brønsted aci...
Chemical syntheses of the bacterial diglucosyl diacylglycerols 1-heptadecanoyl-2-pentadecanoyl-3-O-[6-O-(β-d-glucopyranosyl)-β-d-glucopyranosyl]-sn-glycerol and 1-(cis-13-octadecenoyl)-2-palmitoyl-3...
The outcome of a glycosylation reaction critically depends on the reactivity of all reaction partners involved: the donor glycoside (the electrophile), the activator (that generally provides the leavi...
Carbohydrate/aromatic stacking represents a recurring key motif for the molecular recognition of glycosides, either by protein binding domains, enzymes or synthetic receptors. Interestingly, it has be...
The goal of this study is to better characterize the metabolic alterations and sugar structure alterations (glycosylation abnormalities) in patients diagnosed with Congenital Disorders of ...
This is a prospective cohort study, open-label, uncontrolled proof of concept trial. The trial objective is to evaluate the analgesic tolerability, safety and activity of IDN 5243 (3-glyco...
The purpose of this study is to investigate the coagulation balance in a cohort of congenital disorder of glycosylation (CDG) patients using conventional tests combined with an integrated ...
The objective of the study is to investigate congenital disorders of glycosylation in congenital heart diseases without a clear molecular or genetic basis.
This clinical trial is an investigational research study to determine the ratio of glycosylated FSH21/FSH24 in premenopausal women and postmenopausal women as well as determining if estrad...
The chemical or biochemical addition of carbohydrate or glycosyl groups to other chemicals, especially peptides or proteins. Glycosyl transferases are used in this biochemical reaction.
A genetically heterogeneous group of heritable disorders resulting from defects in protein N-glycosylation.
Enzymes that catalyze the transfer of glycosyl groups to an acceptor. Most often another carbohydrate molecule acts as an acceptor, but inorganic phosphate can also act as an acceptor, such as in the case of PHOSPHORYLASES. Some of the enzymes in this group also catalyze hydrolysis, which can be regarded as transfer of a glycosyl group from the donor to water. Subclasses include the HEXOSYLTRANSFERASES; PENTOSYLTRANSFERASES; SIALYLTRANSFERASES; and those transferring other glycosyl groups. EC 2.4.
Organic chemicals where aryl or alkyl groups are joined by two nitrogen atoms through a double bond (R-N=N-R'; R and R' may be either aryl or alkyl). They may be used as DYES.
A single-pass transmembrane CELL SURFACE RECEPTOR that binds ADVANCED GLYCOSYLATION END PRODUCTS to mediate cellular responses to both acute and chronic vascular inflammation in conditions such as ATHEROSCLEROSIS and DIABETES MELLITUS, TYPE 2 . It also binds AMYLOID BETA PEPTIDES and the alarmins S100A12 and S100 CALCIUM BINDING PROTEIN BETA SUBUNIT.