Abstract:
:The rare N-unsubstituted glucosamine (GlcNH (3)(+)) residues in heparan sulfate (HS) have important biological and pathophysiological roles. However, it is difficult to prepare naturally-occuring, GlcNH(3)(+)-containing oligosaccharides from HS because of their low abundance, as well as the inherent problems in both excising and identifying them. Therefore, the ability to chemically generate a series of structurally-defined oligosaccharides containing GlcNH(3)(+) residues would greatly contribute to investigating their natural role in HS. In this study, a series of heparin/HS oligosaccharides, from dp6 up to dp16 in length that possess internal GlcNH(3)(+) residues were prepared by a combination of chemical modification and heparinase I digestion. Purification and structural analysis of the major species derived from the octa- to dodeca-saccharide size fractions indicated the introduction of between 1 and 3 internal GlcNH(3)(+) residues per oligosaccharide. In addition, a GlcNH(3)(+) residue was selectively introduced into an internal position in a tetrasaccharide species by direct chemical modification. This selectivity has potential as an alternative procedure for preparing internally-modified oligosaccharides of various lengths. The utility of such oligosaccharides was demonstrated by a comparison of the binding of three different tetrasaccharide species containing 0, 1 and 2 free amino groups to the NK1 truncated variant of hepatocyte growth factor/scatter factor.
journal_name
Glycoconj Jjournal_title
Glycoconjugate journalauthors
Wei Z,Deakin JA,Blaum BS,Uhrín D,Gallagher JT,Lyon Mdoi
10.1007/s10719-011-9352-3subject
Has Abstractpub_date
2011-12-01 00:00:00pages
525-35issue
8-9eissn
0282-0080issn
1573-4986journal_volume
28pub_type
杂志文章abstract::A straight forward synthesis of a heptasaccharide part of the cell-wall lipopolysaccharide of Mycobacterium gordonae strain 990, known to have antigenicity, has been achieved in excellent yield. Judicious choice of protecting groups in the intermediates played a significant role throughout the synthesis. Most of the i...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-008-9142-8
更新日期:2008-12-01 00:00:00
abstract::The small keratan sulphate proteoglycan, fibromodulin, has been isolated from pooled human articular cartilage. The main chain repeat region and the chain caps from the attached N-linked keratan sulphate chains have been fragmented by keratanase II digestion, and the oligosaccharides generated have been reduced and is...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1018552913584
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abstract::The partial oligosaccharide sequences of glycoconjugates and the nature of their glycosidic linkages were investigated in normal human prostate, benign prostatic hyperplasia (BPH) and prostatic carcinoma by means of lectin histochemistry, using light microscopy and Western blot analysis. The labeling pattern of BPH di...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1007012514118
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abstract::The structures of the branched capsular polysaccharides of group B streptococcus type III (GBSIIIPS) and Streptococcus pneumoniae type 14 (Pn14PS) are identical apart from the (α2→3)-linked sialic acid in the side chains of GBSIIIPS. The present study tries to determine the minimal epitope in GBSIIIPS, using both a pa...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-011-9354-1
更新日期:2011-12-01 00:00:00
abstract::Sialosyl-Le(x) (SLex) and its positional isomer sialosyl-Le(a) are the epitopes recognized by the lectin domain of E- and P-selectins. Expression of SLex in polymorphonuclear leukocytes (PMN) plays an important role in recruitment of these cells at sites of inflammation through activation of selectins. We studied expr...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731223
更新日期:1994-06-01 00:00:00
abstract::Using a focused glycan-gene microarray, we compared the glycosyltransferase (GT) and sulfotransferase gene expression profiles of human monocytes, dendritic cells (DCs) and macrophages (Mphis), isolated or differentiated from the same donors. Microarray analysis indicated that monocytes express transcripts for a full ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-009-9244-y
更新日期:2009-12-01 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::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
abstract::Comparing the properties of 'young' and senescent ('aged') O+ erythrocytes isolated by applying ultracentrifugation in a self-forming Percoll gradient, we demonstrate that the sialic acids of membrane glycoconjugates control the life span of erythrocytes and that the desialylation of glycans is responsible for the cle...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731328
更新日期:1995-06-01 00:00:00
abstract::Frog integumentary mucin B.1 (FIM-B.1) represents a polymorphic extracellular mosaic protein which contains tandemly arranged serine/threonine-rich modules as well as cysteine-rich domains. The latter are probably important for oligomerization of FIM-B.1 and have also been found in many proteins of the complement casc...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00702337
更新日期:1996-10-01 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::Proteoglycans and glycosaminoglycans modulate numerous cellular processes relevant to tumour progression, including cell proliferation, cell-matrix interactions, cell motility and invasive growth. Among the glycosaminoglycans with a well-documented role in tumour progression are heparan sulphate, chondroitin/dermatan ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-016-9735-6
更新日期:2017-06-01 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::The expression of neutral glycosphingolipids and gangliosides has been studied in human skeletal and heart muscle using indirect immunofluorescence microscopy. Transversal and longitudinal cryosections were immunostained with specific monoclonal and polyclonal antibodies against the neural glycosphingolipids lactosylc...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731284
更新日期:1994-10-01 00:00:00
abstract::In this study, a novel water soluble polysaccharide (named GFP-4) was extracted from Grifola frondosa at 4 oC, and its preliminary structure and inhibitory effects on human gastric carcinoma MKN-45 cells through the Fas/FasL death receptor apoptosis pathway were investigated. High-performance gel permeation chromatogr...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-020-09932-0
更新日期:2020-08-01 00:00:00
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journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-008-9175-z
更新日期:2009-02-01 00:00:00
abstract::Disialosyl globopentaosylceramide (DSGb5) is a ganglioside originally isolated from tissue extracts of renal cell carcinoma (RCC) with metastasis. Previous in vitro experiments have suggested that DSGb5 promotes metastasis by enhancing the migration of RCC cells and downregulating NK cell cytotoxicity against RCC cell...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-017-9763-x
更新日期:2017-04-01 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::Podocalyxin (PC) was first identified as a heavily sialylated transmembrane protein of glomerular podocytes. Recent studies suggest that PC is a remarkable glycoconjugate that acts as a universal glyco-carrier. The glycoforms of PC are responsible for multiple functions in normal tissue, human cancer cells, human embr...
journal_title:Glycoconjugate journal
pub_type: 杂志文章,评审
doi:10.1007/s10719-016-9757-0
更新日期:2017-04-01 00:00:00
abstract::N-acetylglucosaminyltransferase (GnT)-IV a is a key enzyme that catalyzes the formation of the GlcNAC β1-4 branch on the core structure of complex N-Glycans, which is the common substrate for other N-acetylglucosaminyltransferases, such as GnT-III and GnT-V. Our recent study indicates that the expression of GnT-IVa in...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-012-9414-1
更新日期:2012-08-01 00:00:00
abstract::Egg yolk, a large proportion of the egg, was studied for the preparation of N-acetylneuraminic acid (Neu5Ac). The delipidated hen egg yolk (DEY; 500 kg containing 0.2% w/w, Neu5Ac) was hydrolysed with HCl (pH 1.4) at 80 degrees C and neutralized with NaOH (pH 6.0). The mixture was filtered and electrodialysed until th...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731701
更新日期:1992-04-01 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::Rice (Oryza sativa) expresses different putative carbohydrate-binding proteins belonging to the class of lectins containing an Euonymus lectin (EUL)-related domain, one of them being OrysaEULS2. The OrysaEULS2 sequence consists of a 56 amino acid N-terminal domain followed by the EUL sequence. In this paper the origin...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-012-9405-2
更新日期:2012-10-01 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::Previous studies had established an over-expression of 9-O-acetylated sialoglycoproteins (Neu5,9Ac(2)-GPs) on lymphoblasts of childhood acute lymphoblastic leukaemia (ALL). Here, we report the discovery and characterization of sialate-O-acetyltransferase enzyme in ALL-cell lines and lymphoblasts from bone marrow of ch...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-008-9163-3
更新日期:2009-01-01 00:00:00
abstract::Cultured chondrocytes derived from the caudal and cephalic ends of embryonic chick sterna have been compared with each other and with whole sternum, by using a panel of 21 lectins to probe the distribution of oligosaccharides in glycoconjugates of cells and matrix at various times of culture or development. On culture...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1018526813159
更新日期:1997-04-01 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::A major impediment in the analysis of glycosaminoglycans is the difficulty to cleave quantitatively the glycosidic bonds because of the stabilisation of glycosidic bonds and of the relative instability of the liberated constituents. This manuscript describes a modified procedure of methanolysis in the presence of bari...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1007076900562
更新日期:1999-10-01 00:00:00
abstract::CLEC-2 was first identified by sequence similarity to C-type lectin-like molecules with immune functions and has been reported as a receptor for the platelet-aggregating snake venom toxin rhodocytin and the endogenous sialoglycoprotein podoplanin. Recent researches indicate that CLEC-2-deficient mice were lethal at th...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-012-9415-0
更新日期:2012-08-01 00:00:00
abstract::UDP-GlcNAc:alpha3-D-mannoside beta1,2- N -acetylglucosaminyltransferase I (GnTI; EC 2.4.1.101) is a Golgi-resident glycosyltransferase that is essential for the processing of oligomannose to hybrid and complex N-glycans in higher eukaryotes. The cDNA of Nicotiana tabacum GnTI has been cloned and characterised previous...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/B:GLYC.0000045099.29038.04
更新日期:2004-01-01 00:00:00