Abstract:
:As part of our ongoing program aimed at understanding the structural significance of GlcNAcβAsn linkage conserved in all eukaryotic N-glycoproteins, the present study reports on the synthesis and X-ray crystal structures of N-(3-deoxy-3-acetamido-β-D-glycopyranosyl)acetamide (Glc3NAcβNHAc) and the corresponding propionamide (Glc3NAcβNHPr). Comparative analysis of these structures with those of the corresponding GlcNAc (C2 acetamido) compounds showed that the bifurcated anti-parallel pattern involving N-H…O and C-H…O hydrogen bonds, the hallmark feature of the N-glycoprotein models, GlcNAcβNHAc and GlcNAcβAsn, is absent in both the C3 acetamido analogs. The extended (anti) conformation of the amido aglycon moiety as defined by χ(2) seen in the case of C2 acetamido derivative, GlcNAcβNHPr, turns into gauche for the C3 acetamido analog (Glc3NAcβNHPr). This observation is consistent with the earlier work on the critical role of the C2-NHAc group of GlcNAcβAsn in controlling χ(2) at the linkage region of N-glycoproteins.
journal_name
Glycoconj Jjournal_title
Glycoconjugate journalauthors
Mathiselvam M,Varghese B,Loganathan Ddoi
10.1007/s10719-011-9357-ysubject
Has Abstractpub_date
2011-12-01 00:00:00pages
573-80issue
8-9eissn
0282-0080issn
1573-4986journal_volume
28pub_type
杂志文章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::Recently, we demonstrated that the human xylosyltransferase II (XT-II) has enzymatic activity and is able to catalyze the initial and rate-limiting step in the biosynthesis of glycosaminoglycans (GAGs) like chondroitin and dermatan sulfate, as well as heparan sulfate and heparin. Therefore, this enzyme also very likel...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-012-9439-5
更新日期:2013-04-01 00:00:00
abstract::Glycosphingolipids were prepared from pig lung and pooled into two fractions with (i) < or = 3 sugar residues, and (ii) > or = 3 sugar residues. Oligosaccharides were prepared and used for gas chromatography, gas chromatography/mass spectrometry and matrix-assisted laser desorption/ionization mass spectrometry. The gl...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1006901803636
更新日期:1999-01-01 00:00:00
abstract::A sialoglycopeptide was isolated from buffalo colostrum in pure form by chromatography on Sephadex G-25 and QAE-Sephadex A-25. This was found to be homogeneous by cellulose acetate membrane electrophoresis and reverse phase HPLC. It consisted of fucose, galactose, mannose, N-acetyl glucosamine and N-acetyl neuraminic ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF01049681
更新日期:1996-02-01 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::This review summarizes fifty years of carbohydrate chemistry, from studies of reaction mechanisms and development of synthetic methods to the design of specific compounds for investigations of cancer glycoproteins. Through these years of intensive research, many carbohydrate derivatives were shown to be biologically r...
journal_title:Glycoconjugate journal
pub_type: 杂志文章,评审
doi:10.1023/a:1022244324787
更新日期:2001-11-01 00:00:00
abstract::Various oligosaccharides containing galactose(s) and one glucosamine (or N-acetylglucosamine) residues with beta1-4, alpha1-6 and beta1-6 glycosidic bond were synthesized; Galbeta1-4GlcNH(2), Galalpha1-6GlcNH(2), Galalpha1-6GlcNAc, Galbeta1-6GlcNH(2), Galbeta1-4Galbeta1-4GlcNH(2) and Galbeta1-4Galbeta1-4GlcNAc. Galalp...
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::Coarse tea is made of mature tea plant (Camellia sinensis L.) shoots and is generally discarded as a worthless crop product, but has been proved an excellent material for the treatment of diabetes. This study aims to evaluate the effects of the extraction techniques WE (water extraction), UAE (ultrasound-assisted extr...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-019-09901-2
更新日期:2020-04-01 00:00:00
abstract::Humans, in contrast to other mammals, do not synthesize N-glycolyl-neuraminic acid (Neu5Gc) due to a deletion in the gene (cmah) encoding the enzyme responsible for this conversion, the cytidine monophospho-N-acetyl-neuraminic acid hydroxylase (CMP-Neu5Ac hydroxylase). The detection of considerable amounts of Neu5Gc-s...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-013-9473-y
更新日期:2013-10-01 00:00:00
abstract::Rotaviruses are the leading cause of childhood diarrhea. The entry of rotaviruses into the host cell is a complex process that includes several interactions of the outer layer proteins of the virus with different cell surface molecules. The fact that neuraminidase treatment of the cells, or preincubation of the virus ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章,评审
doi:10.1007/s10719-006-5435-y
更新日期:2006-02-01 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 human glioma D-54MG cell line grown in vitro primarily expresses ganglio series gangliosides, particularly GM2. Subcutaneous injection of these cells into nude mice produced xenografts with an increased content of the human glioma-associated lacto series gangliosides, primarily 3'-isoLM1, an alteration that was do...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731472
更新日期:1996-06-01 00:00:00
abstract::As an adjunct to existing thin layer and column chromatographic methods for the identification of glycolipids a method that utilizes the high pH anion chromatographic (HPAEC) analysis of the oligosaccharides released from the glycolipids by endoglycoceramidase has been developed. Using a Dionex Carbo Pak PA1 column an...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731225
更新日期:1994-06-01 00:00:00
abstract::Non-acid and acid glycosphingolipids were isolated from feces of one litter of germ-free rats from day 17 to day 51. Quantitative and qualitative changes described for small intestine of conventional rats [Bouhours D, Bouhours J-F (1981) Biochem Biophys Res Commun 99:1384-89] were also found in the feces of these germ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF01047848
更新日期:1989-01-01 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::A novel cold-water-soluble polysaccharide (BEP), with a molecular weight of 6.0 × 106 Da, was isolated from Boletus edulis. BEP consists of galactose, glucose, xylose, mannose, glucuronic, and galacturonic acid in a ratio of 0.34:0.28:0.28:2.57:1.00:0.44. The IR results showed that BEP was an acid polysaccharide, cont...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-021-09972-0
更新日期:2021-01-28 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::This review discusses the challenges facing research in 'functional glycomics' and the novel technologies that are being developed to advance the field. The structural complexity of glycans and glycoconjugates makes studies of both their structures and recognition difficult. However, these intricate structures can be ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章,评审
doi:10.1007/s10719-015-9584-8
更新日期:2015-10-01 00:00:00
abstract::Grifola frondosa is an important fungal research resource. However, there was little report about hyperglycemic activity of Grifola frondosa polysaccharide on insulin resistance in vitro. In this study, the hypoglycemic activity of a polysaccharide obtained from Grifola frondosa (GFP) on HepG2 cell and hpyerglycemic m...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-014-9526-x
更新日期:2014-07-01 00:00:00
abstract::We report the postnatal developmental profiles of N-acetylneuraminic acid cytidylyltransferase (EC 2.7.7.43) (CMP-Neu5Ac synthetase) in different rat tissues. This enzyme, which catalyses the activation of NeuAc to CMP-Neu5Ac, was detected in brain, kidney, heart, spleen, liver, stomach, intestine, lung, thymus, prost...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1006940927639
更新日期:1998-03-01 00:00:00
abstract::The N-glycans from soluble extracts of ten pollens were examined. The pyridylaminated oligosaccharides derived from these sources were subject to gel filtration and reverse-phase HPLC, in conjunction with exoglycosidase digests, and in some cases matrix-assisted laser desorption-ionisation mass spectrometry. In compar...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1006960401562
更新日期:1998-11-01 00:00:00
abstract::Human β-1,4-galactosyltransferase (β-1,4-GalT) V was shown to be involved in the biosynthesis of N-glycans, O-glycans and lactosylceramide (Lac-Cer) by in vitro studies. To determine its substrate specificity, enzymatic activity and its products were analyzed using mouse embryonic fibroblast (MEF) cells from β-1,4-Gal...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-010-9313-2
更新日期:2010-10-01 00:00:00
abstract::Fucosylated oligosaccharides have an important role in maintaining a healthy immune system and homeostatic gut microflora. This study employed a commercial β-galactosidase in the production of fucose-containing galacto-oligosaccharides (fGOS) from lactose and fucose. The production was optimized using experiment desig...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-017-9794-3
更新日期:2018-02-01 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::Cell surface lipopolysaccharide (LPS) is a well characterized virulence determinant for the human pathogen Haemophilus influenzae, so an investigation of LPS in the less pathogenic Haemophilus parainfluenzae could yield important insights. Using a panel of 18 commensal H. parainfluenzae isolates we demonstrate that th...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-012-9455-5
更新日期:2013-08-01 00:00:00
abstract::Poly-N-acetyllactosamine (poly-LacNAc) structures have been identified as important ligands for galectin-mediated cell adhesion to extra-cellular matrix (ECM) proteins. We here present the biofunctionalization of surfaces with poly-LacNAc structures and subsequent binding of ECM glycoproteins. First, we synthesized be...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-008-9172-2
更新日期:2009-02-01 00:00:00
abstract::The sugar chain-binding specificity of tomato lectin (LEA) against glycoproteins was investigated qualitatively using lectin blot analysis. Glycoproteins containing tri- and tetra-antennary complex-type N-glycans were stained with LEA. Unexpectedly, glycoproteins containing high mannose-type N-glycans and a horseradis...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-005-5329-4
更新日期:2005-11-01 00:00:00
abstract::In aging and diabetes, glycation of collagen molecules leads to the formation of cross-links that could alter the surface charge on collagen fibrils, and hence affect the properties and correct functioning of a number of tissues. The electron-optical stain phosphotungstic acid (PTA) binds to positively charged amino a...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1006928403140
更新日期:1998-08-01 00:00:00
abstract::Over the last few years enormous interest has been shown in the structures of the glycan moieties of various parasite surface glycoconjugates. Structures have been determined for the glyco-components of glycosylphosphatidylinositol (GPI) protein membrane anchors, for asparagine-linked oligosaccharides, and for the gly...
journal_title:Glycoconjugate journal
pub_type: 杂志文章,评审
doi:10.1007/BF00769843
更新日期:1991-12-01 00:00:00
abstract::Synthetic thioglycoside-analogs of gangliosides such as Neu5Ac alpha(2-S-6)Glc beta(1-1)Ceramide (1) and the GM3 analog Neu5Ac alpha(2-S-6)Gal beta(1-4)Glc beta(1-1)Ceramide (2), competitively inhibited GM3 hydrolysis by the sialidase of different subtypes of human and animal influenza viruses with an apparent Ki valu...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF01073378
更新日期:1990-01-01 00:00:00