Abstract:
:UDP-GlcNAc:Man alpha 1-3R beta 1-2-N-acetylglucosaminyltransferase I (GlcNAc-T I; EC 2.4.1.101) catalyses the conversion of [Man alpha 1-6(Man alpha 1-3)Man alpha 1-6][Man alpha 1-3]Man beta-O-R to [Man alpha 1-6(Man alpha 1-3)Man alpha 1-6] [GlcNAc beta 1-2Man alpha 1-3]Man beta-O-R (R = 1-4GlcNAc beta 1-4GlcNAc- Asn-X) and thereby controls the conversion of oligomannose to complex and hybrid asparagine-linked glycans (N-glycans). GlcNAc-T I also catalyses the conversion of Man alpha 1-6(Man alpha 1-3)Man beta-O-octyl to Man alpha 1-6(GlcNAc beta 1-2Man alpha 1-3)Man beta-O-octyl. We have therefore tested a series of synthetic analogues of Man"alpha 1-6(Man'alpha 1-3)Man beta-O-octyl as substrates and inhibitors for rat liver GlcNAc-T I. The 2"-deoxy and the 3"-, 4"- and 6"-O-methyl derivatives are all good substrates confirming previous observations that the hydroxyl groups of the Man"alpha 1-6 residue do not play major roles in the binding of substrate to enzyme. In contrasts, all four hydroxyl groups on the Man'alpha 1-3 residue are essential since the corresponding deoxy derivatives either do not bind (2'- and 3'-deoxy) or bind very poorly (4'- and 6'-deoxy) to the enzyme. The 2'- and 3'-O-methyl derivatives also do not bind to the enzyme. However, the 4'-O-methyl derivative is a substrate (KM = 2.6 mM) and the 6'-O-methyl compound is a competitive inhibitor (Ki = 0.76 mM). We have therefore synthesized various 4'- and 6'-O-alkyl derivatives, some with reactive groups attached to an O-pentyl spacer, and tested these compounds as reversible and irreversible inhibitors of GlcNAc-T I. The 6'-O-(5-iodoacetamido-pentyl) compound is a specific time dependent inhibitor of the enzyme. Four other 6'-O-alkyl compounds showed competitive inhibition while the remaining compounds showed little or no binding indicating that the electronic properties of the attached O-pentyl groups influence binding.
journal_name
Glycoconj Jjournal_title
Glycoconjugate journalauthors
Reck F,Springer M,Meinjohanns E,Paulsen H,Brockhausen I,Schachter Hdoi
10.1007/BF00731234subject
Has Abstractpub_date
1995-12-01 00:00:00pages
747-54issue
6eissn
0282-0080issn
1573-4986journal_volume
12pub_type
杂志文章abstract::Filamentous fungi are commonly used in the fermentation industry for large scale production of glycoproteins. Several of these proteins can be produced in concentrations up to 20-40 g per litre. The production of heterologous glycoproteins is at least one or two orders of magnitude lower but research is in progress to...
journal_title:Glycoconjugate journal
pub_type: 杂志文章,评审
doi:10.1023/a:1026436424881
更新日期:1999-02-01 00:00:00
abstract::Reductive amination of 3-deoxy-D-manno-octulosonic acid (Kdo) with allylamine (AIIN) or 2-(4-aminophenyl)ethylamine (APEA) yields epimer pairs of 2-N-allylamino and 2-N-[2-(4-aminophenyl)ethylamino]-2,3-dideoxy-D-glycero-D-galacto- and -2,3-dideoxy-D-glycero-D-talo-octonic acid. The yields were 50-60% due to reduction...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1006955508077
更新日期:1998-06-01 00:00:00
abstract::The Maillard reaction was discovered in 1912 by Louis C. Maillard when he observed the browning phenomena with aroma formation in a heated solution containing a sugar and an amino acid. The Maillard reaction starts from the reactions between carbonyl groups of various sugars and amino groups of amino acids/ proteins, ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章,评审
doi:10.1007/s10719-020-09943-x
更新日期:2020-09-10 00:00:00
abstract::If we predict the host range of new or mutant influenza virus in advance, we are able to measure against pandemic human influenza immediately after the new virus emerges somewhere. Influenza viral hemagglutinin(HA)-sialoside receptor interaction is a target event for in silico chemical prediction studies about the vir...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-008-9141-9
更新日期:2008-12-01 00:00:00
abstract::Oral exposure to lectins or the presence or absence of bacteria in the rat small intestine were shown by histological methods using anti-lectin antibodies or digoxigenin-labelled lectins to have major effects on the state of glycosylation of lumenal membranes and cytoplasmic glycoconjugates of epithelial cells. Taken ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731865
更新日期:1995-02-01 00:00:00
abstract::Glycosylation is a very important post-translational modification involved in various cellular processes, such as cell adhesion, signal transduction and immune response. Urine is a rich source of glycoproteins and attractive biological fluid for biomarker discovery, owing to its availability, ease of collection, and c...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-016-9677-z
更新日期:2016-12-01 00:00:00
abstract::The novel glycosphingolipid, SEGLx (Galbeta1-4(Fucalpha1-3)Glcbeta1-3GalbetaCer), which was identified by us (Kawakami Y, et al. (1993) J Biochem 114: 677-83), shows a characteristic spectrum on 1H-NMR analysis, in which the anomeric proton resonances of a reducing end galactose and a glucose are split. To elucidate t...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1006908020370
更新日期:1998-02-01 00:00:00
abstract::Twenty different human and animal tissues were investigated for the presence of polyglycosylceramides. The glycolipids were isolated by peracetylation of dry tissue residues left after conventional lipid extraction, followed by extraction with chloroform and subsequent Sephadex LH-20, Sephadex LH-60 and silica gel chr...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1018545922728
更新日期:1997-02-01 00:00:00
abstract::In this work, we characterized chemically the N-acetyl-D-galactosamine specific lectin from Amaranthus leucocarpus syn hypocondriacus lectin (ALL). It is a dimeric glycoprotein composed by three isoforms with pl at 4.8, 4.9, and 5.2. Circular dichroism analysis indicated that the secondary structure of ALL contains 45...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1013760915738
更新日期:2001-04-01 00:00:00
abstract::Duffy antigen/receptor for chemokines (DARC) is a glycosylated seven-transmembrane protein acting as a blood group antigen, a chemokine binding protein and a receptor for Plasmodium vivax malaria parasite. It is present on erythrocytes and endothelial cells of postcapillary venules. The N-terminal extracellular domain...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-011-9367-9
更新日期:2012-04-01 00:00:00
abstract::Potato lectin (Solanum tuberosum agglutinin, STA) is an unusual glycoprotein containing approximately 50% carbohydrates by weight. Of the total carbohydrates, 92% is contributed by L: -arabinose, which are O-linked to hydroxyproline residues. The ferric chloride-orcinol assay (Bial's test), which is specific for pento...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-006-6217-2
更新日期:2006-11-01 00:00:00
abstract::Proteoglycans contain a unique carbohydrate component, glycosaminoglycan, which consists of repeating, typically sulfated disaccharides, and is capable of interacting with diverse molecules. Specific, clustered arrangements of sulfate on the glycosaminoglycan backbone form binding sites for many biologically important...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-008-9138-4
更新日期:2009-11-01 00:00:00
abstract::Infectious disease, commonly caused by bacterial pathogens, is now the world's leading cause of premature death and third overall cause behind cardiovascular disease and cancer. Urinary Tract Infection (UTI), caused by E. coli bacteria, is a very common bacterial infection, a majority in women (85%) and may result in ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-004-5539-1
更新日期:2004-01-01 00:00:00
abstract::The uncovering enzyme (UCE) removes N-acetylglucosamine from lysosomal enzymes to uncover the mannose 6-phosphate (Man-6-P) determinant necessary for targeting these enzymes to lysosomes. Failure to create the Man-6-P determinant is one cause of lysosomal storage diseases. Despite its medical importance, little struct...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-005-0846-8
更新日期:2005-02-01 00:00:00
abstract::Because anti-glycolipid antibodies are involved in the onset of several neurological diseases, the reactivity of glycolipids on erythrocytes and the probability of generating the antibodies were determined to clarify the contribution of glycolipids as antigens. Anti-erythrocyte antisera reacted with the following glyc...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-008-9197-6
更新日期:2009-05-01 00:00:00
abstract::The intestinal pathogen Escherichia coli serotype O104:H4 (ECO104) can cause bloody diarrhea and haemolytic uremic syndrome. The ECO104 O antigen has the unique repeating unit structure [4Galα1-4Neu5,7,9Ac3α2-3Galβ1-3GalNAcβ1-], which includes the mammalian sialyl-T antigen as an internal structure. Previously, we ide...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-017-9799-y
更新日期:2018-02-01 00:00:00
abstract::The metabolism of glycosphingolipids is strictly regulated during the mitotic cell cycle. Before the G1-to-S transition, the ceramide and glucosylceramide concentration is elevated. Ceramide induces apoptosis synergistically with the pro-apoptotic protein prostate apoptosis response 4 (PAR-4) that may be asymmetricall...
journal_title:Glycoconjugate journal
pub_type: 杂志文章,评审
doi:10.1023/B:GLYC.0000046274.35732.47
更新日期:2004-01-01 00:00:00
abstract::Matrix proteoglycans (PGs) have shown promise as biomarker in malignancies. We employed agarose gel eletrophoresis, quantitative real- time reverse transcription-polymerase chain reaction and immunohistochemistry to evaluate the content of sulfated glicosaminoglycans (chondroitin sulfate and heparan sulfate) and expre...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-018-9815-x
更新日期:2018-04-01 00:00:00
abstract::A non-enzymatic reaction between sugars or aldehydes and the amino groups of proteins, lipids and nucleic acids contributes to the aging of macromolecules, which could impair their structural integrity and function. This process begins with the conversion of reversible Schiff base adducts, and then to more stable, cov...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-016-9682-2
更新日期:2016-08-01 00:00:00
abstract::The TF, Tn, and SiaTn glycotopes are frequently expressed in cancer-associated mucins. Antibodies to these glycotopes were found in human serum. A set of polyacrylamide (PAA)--based glycoconjugates was applied to the direct and competitive enzyme-linked immunosorbent assays (ELISA) to characterize the specificity of s...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/B:GLYC.0000018582.83813.04
更新日期:2004-01-01 00:00:00
abstract::The importance of the surrounding lipid environment on the availability of glycolipid carbohydrate for ligand binding was demonstrated by studying the influence of phosphatidylcholine fatty acid chain length on binding of verotoxins (VT1 and VT2c) to their specific cell surface receptor, globotriaosylceramide (Gb3) in...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731490
更新日期:1996-04-01 00:00:00
abstract::Transmembrane signaling requires modular interactions between signaling proteins, phosphorylation or dephosphorylation of the interacting protein partners and temporary elaboration of supramolecular structures, to convey the molecular information from the cell surface to the nucleus. Such signaling complexes at the pl...
journal_title:Glycoconjugate journal
pub_type: 杂志文章,评审
doi:10.1023/a:1026585006064
更新日期:2000-03-01 00:00:00
abstract::Two Arabidopsis xylosyltransferases, designated RGXT1 and RGXT2, were recently expressed in Baculovirus transfected insect cells and by use of the free sugar assay shown to catalyse transfer of D-xylose from UDP-alpha-D-xylose to L-fucose and derivatives hereof. We have now examined expression of RGXT1 and RGXT2 in Pi...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-009-9242-0
更新日期:2009-12-01 00:00:00
abstract::Herein we describe a UPLC-FLD-based method for the quantification of the sialic acid content of red meat, using a synthetic neuraminic acid derivative as an internal standard. X-Gal-α-2,6-N-propionylneuraminic acid was synthesized via a chemoenzymatic pathway and its hydrolytic stability was characterized. Known quant...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-016-9659-1
更新日期:2016-04-01 00:00:00
abstract::UDP-GlcNAc:alpha6-D-mannoside beta1,2-N-acetylglucosaminyltransferase II (GnT II; EC 2.4.1.143) is a medial-Golgi resident enzyme that catalyses an essential step in the biosynthetic pathway leading from high mannose to complex N-linked oligosaccharides. Screening a cDNA library from Xenopus laevis ovary with a human ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/A:1024201824354
更新日期:2002-03-01 00:00:00
abstract::We analyzed surface glycoproteins of human natural killer (NK) cells by utilizing lectins. Among the lectins tested, wheat germ agglutinin (WGA) was found to bind preferentially to CD16(Leu11)-positive lymphocytes as determined by two-colour flow cytometry. Analysis of glycoproteins in the lysate prepared from NK cell...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731165
更新日期:1992-08-01 00:00:00
abstract::To elucidate the biological significance of the lactosylceramide (LacCer) branching in glycosphingolipid (GSL) biosynthesis, we established ganglioside GM3- and lactosylsulfatide SM3-reconstituted cells by introducing the GM3 synthase gene and the sulfotransferase gene, respectively. In SM3-expressing cells, the reduc...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/B:GLYC.0000024248.62242.1f
更新日期:2004-01-01 00:00:00
abstract::Three-dimensional structures of the natural substrate unit for the enzyme N-acetylglucosamine-transferase II, GIcNAc-Man3-GlcNAc2, were investigated by molecular modelling methods. Molecular dynamics (MD) and molecular mechanics calculations on two hexasaccharides, namely GlcNAc-Man3-GlcNAc2-Asn and GlcNAc-Man3-GlcNAc...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1006976408074
更新日期:1998-02-01 00:00:00
abstract::Mammalian sulfoglycolipids are comprised of two major members, sulfatide (SO(3)-3Gal-ceramide) and seminolipid (SO(3)-3Gal-alkylacylglycerol). Sulfatide is abundant in the myelin sheath and seminolipid is expressed on the spermatogenic cells. Cerebroside sulfotransferase (CST)-deficient mice generated by gene targetin...
journal_title:Glycoconjugate journal
pub_type: 杂志文章,评审
doi:10.1023/B:GLYC.0000043749.06556.3d
更新日期:2004-01-01 00:00:00
abstract::Heteropolysaccarides were isolated from the Korean medicinal plant, Phellodendri cortex (Hwangbek), by hot water and alkali extractions. The extracted polysaccharides were fractionated into eight fractions and they are mainly composed of D-N-acetylglucosamine, D-galactose, D-mannose, and D-glucose. Among the polysacch...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1007084506071
更新日期:1999-03-01 00:00:00