glycosylation

1-Deoxymannojirimycin hydrochloride, a selective α1,2-mannosidase inhibitor (IC50: 20 μM), also inhibits HIV-1 strains but exhibits poor antiviral activity.

Robinetin (3,3',4',5',7-Pentahydroxyflavone) exhibits potent antioxidant and antiradical activities, effectively inhibiting EYPC membrane lipid peroxidation and HbA glycosylation.

Benzyl-α-GalNAc (O-glycosylation-IN-1) is a potent inhibitor of O-glycosylation and is used to reduce mucin on cell surfaces.

T3Inh-1 is a potent and selective ppGalNAc-T3 inhibitor with IC50 of 7 µM. T3Inh-1 protects against breast cancer cells. T3Inh-1 reduces FGF23 hormone levels in tissue cells and mice without causing any toxic side effects.

Tunicamycin is a mixture of antibiotics that inhibit N-linked glycosylation by blocking GlcNAc phosphotransferase (GPT). Tunicamycin has antitumor activity, as well as anti-bacterial, anti-fungal, and anti-viral activity.

Pyrimidine (Metadiazine)s are heterocyclic, six-membered, nitrogen-containing carbon ring structures, with uracil, cytosine and thymine being the basal structures of ribose-containing nucleosides (uridine, cytidine, and thymidine respectively), or deoxyribose-containing deoxynucleosides, and their corresponding ribonucleotides or deoxyribonucleotides. Pyrimidines serve essential functions in human metabolism as ribonucleotide bases in RNA (uracil and cytosine), and as deoxyribonucleotide bases in DNA (cytosine and thymine), and are linked by phosphodiester bridges to purine nucleotides in double-stranded DNA, in both the nucleus and the mitochondria. Pyrimidine activated sugars are also involved in polysaccharide and phospholipid synthesis, glucuronidation in detoxification processes, glycosylation of proteins and lipids and in the recently identified novel endothelium-derived vasoactive dinucleotides.

D-Mannose (D-(+)-Mannose) is a carbohydrate. D-Mannose plays an important role in human metabolism, especially in the glycosylation of specific proteins.

D-(+)-Xylose (Wood sugar) is an aldopentose - a monosaccharide containing five carbon atoms and an aldehyde functional group. It has chemical formula C5H10O5 and is 40% as sweet as sucrose. Xylose is also found in mucopolysaccharides of connective tissue and sometimes in the urine. Xylose is the first sugar added to serine or threonine residues during proteoglycan type O-glycosylation. Therefore xylose is involved in the biosythetic pathways of most anionic polysaccharides such as heparan sulphate and chondroitin sulphate. In medicine, xylose is used to test for malabsorption by administering a xylose solution to the patient after fasting. If xylose is detected in the blood and/or urine within the next few hours, it has been absorbed by the intestines. Xylose is said to be one of eight sugars which are essential for human nutrition, the others being galactose, glucose, mannose, N-acetylglucosamine, N-acetylgalactosamine, fucose, and sialic acid. . Xylose in the urine is a biomarker for the consumption of apples and other fruits.

2,2-Dihydroxyacetic acid (Formylformic acid) is an intermediate in the glyoxalate cycle, which enables certain organisms to convert fatty acids to carbohydrates.2,2-Dihydroxyacetic acid has been found to be associated with primary hyperoxaluria, an inborn error of metabolism. As an aldehyde, glyoxalate is also highly active and can modify proteins to form advanced glycosylation products (AGEs).

Galactose is a monosaccharide and hexose sugar widely present in most living cells, primarily absorbed into the bloodstream via SGLT1 and GLUT2 transporters and metabolised through the Leloir pathway. It inhibits alglucerase activity in monkey kidney CoS-1 cells, is a key component of cellular glycosylation, and plays a crucial role in neonatal neural development.

6-Methoxytricin, a flavonoid isolated from Centella asiatica, is an inhibitor of aldose reductase (AR) and advanced glycosylation end-products (AGE), and inhibits T-cell proliferation and activation in biologic cells.

N-Desmethyltamoxifen, the principal metabolite of tamoxifen in humans, serves as an efficacious modulator of ceramide metabolism within human AML cells by inhibiting ceramide glycosylation, hydrolysis, and sphingosine phosphorylation. Although it demonstrates weak antiestrogenic properties, it acts as a protein kinase C (PKC) inhibitor with a potency ten times greater than that of tamoxifen.

Caffeic acid 4-O-glucoside (Linocaffein), a glycosylation product of Caffeic acid, reverses Aβ25-35-induced axonal atrophy and induces axonal regeneration in mouse cortical neurons, and can be used in Alzheimer's disease research.

6′SLN is a characteristic glycan found on the surface of cancer-related extracellular vesicles (EVs) and serves as the primary form of protein glycosylation within EVs. Additionally, 6′SLN, a derivative of sialic acid, interacts with hemagglutinins (HAs) from both human and avian influenza strains, making it relevant in the study of anti-influenza drugs.

L-Erythrose (L-(+)-Erythrose) is a tetrasaccharide and an aldose, and oxidizing bacteria are able to use L-Erythrose as their sole source of energy.L-Erythrose is involved in the synthesis of erythritol, and can therefore be used in glycosylation studies and to characterize erythrose reductase (ER) activity.

Kifunensine, an alkaloid discovered in Kitasatosporia kifunense, functions as a glycosylation pathway inhibitor and immunomodulator. It strongly inhibits α-mannosidase I in the Golgi apparatus and may be utilised in studies of endoplasmic reticulum stress.

Glycation-IN-1 (Compound 3) is an inhibitor of the glycosylation reaction, effectively suppressing the synthesis of the initial, intermediate, and final products of glycation reactions. It is applicable in research on various chronic diseases, including diabetes, immune inflammation, cardiovascular diseases, and neurodegenerative disorders.

LacNAc-VC-PAB-MMAE is a component of an antibody-drug conjugate (ADC). It is assembled onto the N-glycosylation site of Trastuzumab through WT Endo-S2.

NGI-235 is a selective OST-A inhibitor that suppresses NF-κB inflammatory signaling by blocking the glycosylation of TLR4.

BACE-IN-1 acetate (BACE-IN-1 acetate (350228-37-4,Free base)) has been used as β-site amyloid precursor protein (APP) cleaving enzyme-1 (BACE1) inhibitor in BACE1 inhibitor assay. β-Site amyloid precursor protein (APP) cleaving enzyme-1 (BACE1), an aspartic protease belongs to the protease family of enzymes comprises of six luminal cysteine residues. These residues help in the formation of three intermolecular disulfide bonds and N-linked glycosylation sites.

Advanced glycation end products (AGEs) are compounds formed by non-enzymatic chemical reactions following the bonding of sugars to proteins or lipids during diabetes, uremia, aging, rheumatic arthritis, and other conditions. A receptor for the AGEs (RAGE) binds certain members of this class to initiate cell signaling.[1][2] Pentosidine is a well-characterized natural AGE that is often used as a biomarker for the production of all AGEs. While pentosidine can be measured in urine, the majority of this AGE is catabolized before excretion.[3] Reference:[1]. Neeper, M., Schmidt, A.M., Brett, J., et al. Cloning and expression of a cell surface receptor for advanced glycosylation end products of proteins. The Journal of Biological Chemisty 267(21), 14998-15004 (1992).[2]. Brett, J., Schmidt, A.M., Yan, S.D., et al. Survey of the distribution of a newly characterized receptor for advanced glycation end products in tissues. American Journal of Pathology 143(6), 1699-1712 (1993).[3]. Miyata, T., Ueda, Y., Horie, K., et al. Renal catabolism of advanced glycation end products: The fate of pentosidine. Kidney International 53, 416-422 (1998).

3,4,6-Tri-O-benzyl-β-D-mannopyranose 1,2-(methyl orthoacetate) is a synthetic intermediate used in glycosylation reactions. Typically, the methyl orthoester protecting group is first removed by mild acid hydrolysis, producing a glycosyl donor. Removal of the O-benzyl protecting groups is performed late in the synthesis.

TunR1 is an antibiotic and derivative of tunicamycin .1It is active againstB. subtilis(MIC = 0.3 μg/ml) and increases the efficacy of the β-lactam antibiotics oxacillin , methicillin , and penicillin G againstB. subtiliswhen used at a concentration of 0.4 μg/ml. TunR1 (5 μg/ml) is cytotoxic to MDA-MB-231 breast cancer cells and non-cancerous CHO cells. Unlike tunicamycin, TunR1 does not inhibit glycosylation in a protein N-glycosylation assay. 1.Price, N.P., Hartman, T.M., Li, J., et al.Modified tunicamycins with reduced eukaryotic toxicity that enhance the antibacterial activity of β-lactamsJ. Antibiot. (Tokyo)70(11)1070-1077(2017)

TunR2 is an antibiotic and derivative of tunicamycin .1It is active againstB. subtilis(MIC = 0.3 μg/ml) and increases the efficacy of the β-lactam antibiotics oxacillin , methicillin , and penicillin G againstB. subtiliswhen used at a concentration of 0.4 μg/ml. Unlike tunicamycin, TunR2 is non-toxic toS. cerevisiae(MIC = >10 μg/ml) and does not inhibit glycosylation in a protein N-glycosylation assay. TunR2 also has reduced antiproliferative activity against MDA-MB-231 and CHO cells compared with tunicamycin. 1.Price, N.P., Hartman, T.M., Li, J., et al.Modified tunicamycins with reduced eukaryotic toxicity that enhance the antibacterial activity of β-lactamsJ. Antibiot. (Tokyo)70(11)1070-1077(2017)