Abstract:
:The conformational space of methyl 6-O-[(R)- and (S)-1-carboxyethyl]-alpha-D-galactopyranoside has been investigated. A grid search employing energy minimization at each grid point over the three major degrees of freedom, namely phi, psi and omega, identified low energy regions. The R-isomer shows five low energy conformers within ca. 1 kcal mol(-1) of the global energy minimum. The S-isomer has two conformers within a few tenths of a kcal mol(-1) of the global energy minimum. Langevin dynamics simulations have been have been performed at 300 K for 30 ns of each isomer. The phi dihedral angle has as its major conformer (g-) for the R-isomer whereas it is the (g+) conformer for the S-isomer. For the psi dihedral angle the (t) conformer has the highest population for both isomers. The dihedral angle omega has the (g+) conformer most highly populated, both for the R- and S-isomer. The above five and two conformational states for the R- and S-isomers, respectively, make up 90% in each case of the populated states during the Langevin dynamics (LD) simulations. Rate constants for the omega dihedral angle have been calculated based on a number correlation function. Three bond homo- and heteronuclear, i.e. proton and carbon-13, coupling constants have been calculated from the dynamics trajectories for comparison to experimental values. The heteronuclear coupling constant H2',C6 has been measured for the S-isomer and found to be 3.3 Hz. The J value calculated from the LD simulations, namely 2.6 Hz, is in fair agreement with experiment. A comparison to the X-ray structure of the R-isomer shows that the conformation of the crystalline compound occupies the low energy region most highly populated as a single R-conformer (30%) during the LD simulations.
journal_name
Glycoconj Jjournal_title
Glycoconjugate journalauthors
Stenutz R,Widmalm Gdoi
10.1023/a:1018527129939subject
Has Abstractpub_date
1997-12-01 00:00:00pages
973-81issue
8eissn
0282-0080issn
1573-4986journal_volume
14pub_type
杂志文章abstract::Since the alpha-D-galactose-(1-->3)-D-galactose epitope has been identified to be the major target in the process of hyperacute rejection of xenografts transplanted from nonprimate donors to humans, specific inhibitors of alpha-galactosyltransferases are of broad interest. Using Trypanosoma brucei, a protozoan parasit...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1007026122209
更新日期:1999-09-01 00:00:00
abstract::A water-soluble polysaccharide CSPS-2B-2 with a molecular mass of 8.8 kDa, was obtained from the fruits of Capparis spinosa L. Chemical and NMR spectral analysis verified CSPS-2B-2 was a linear poly-(1-4)-α-D-galactopyranosyluronic acid in which 12.9±0.4% of carboxyl groups existed as methyl ester and 2.6±0.1% of D-Ga...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-012-9418-x
更新日期:2012-08-01 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::We have previously detected an alkali-labile and developmentally regulated antigen in rat embryonic cerebral cortex, which may be 9-O-acetylsialylated GT3 ganglioside (Hirabayashi Y, Hirota M, Suzuki Y, Matsumoto M, Obata K, Ando S (1989) Neurosci Lett 106:193-98). In this study we established a mouse monoclonal antib...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1018542105832
更新日期:1997-11-01 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::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::The surface of the spermatozoa is coated with glycoproteins the redistribution of which during in vitro capacitation plays a key role in the subsequent fertilization process. Lipid rafts are membrane microdomains involved in signal transduction through receptors and include or recruit specific types of proteins and gl...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-020-09924-0
更新日期:2020-08-01 00:00:00
abstract::Synthesis and antigenic reactivity of 6-O-sulfo sialylparagloboside (SPG) and sialyl Lewis X (sLeX) neo-glycolipids containing lactamized neuraminic acid are described. The suitably protected GlcNAc-beta (1-->3)-Gal-beta (1-->4)-GlcOSE derivative was glycosylated with NeuTFAc-alpha (2-->3)-Gal imidate to give NeuTFAc-...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-005-0352-z
更新日期:2005-03-01 00:00:00
abstract::This review discusses the challenges involved in the characterization of the glycosylation of therapeutic glycoproteins. The focus is on methods that are most commonly used in regulatory filings and lot release testing of therapeutic glycoproteins. The different types of assays for carbohydrate analysis are reviewed, ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章,评审
doi:10.1007/s10719-009-9261-x
更新日期:2010-02-01 00:00:00
abstract::Nucleotide sugar transporters play critical roles in glycosylation of proteins, lipids and proteoglycans, which are essential for organogenesis, development, mammalian cellular immunity and pathogenicity of human pathogenic agents. Functional deficiencies of these transporters result in global defects of glycoconjugat...
journal_title:Glycoconjugate journal
pub_type: 杂志文章,评审
doi:10.1007/s10719-012-9375-4
更新日期:2013-01-01 00:00:00
abstract::Multidisciplinary approaches by a number of investigators have established that cell-surface carbohydrates are integral components of recognition systems regulating survival, migration, adhesion, growth and differentiation of various cells. Our own experience and contributions to this exciting field are described. We ...
journal_title:Glycoconjugate journal
pub_type: 传,历史文章,杂志文章
doi:10.1023/a:1011078627247
更新日期:2000-07-01 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::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::Full proton NMR assignments have been achieved for the alpha(1-3)-linked fucose residues contained in alkaline borohydride reduced keratan sulphate chains derived from bovine articular cartilage. This involved 500 MHz spectroscopy at 60 degrees C and included COSY and RELAYED-COSY determinations. ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731641
更新日期:1991-02-01 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::Human alpha1,3-fucosyltransferase V and -VI (hFucTV and -VI) each contain four potential N-glycosylation sites (hFucTV: Asn60, Asn105, Asn167 and Asn198 and hFucTVI: Asn46, Asn91, Asn153 and Asn184). Glycosylation of the two N-terminal potential N-glycosylation sites (hFucTV: Asn60, Asn105 and hFucTVI: Asn46 and Asn91...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1010917229243
更新日期:2000-12-01 00:00:00
abstract::A monoclonal antibody (mAb 8281) specific for the terminal beta-galactose (beta Gal) of glycosphingolipids (GSL) and glycoproteins was produced from mice immunized with lipid extract from fresh acute lymphocytic leukemia (ALL) cells. Immuno-thin layer chromatography (ITLC) and competition assays with purified neutral ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731643
更新日期:1991-02-01 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::Amphipathic sulpholipids have been shown to inhibit pancreatic serine proteases due to their detergent-like properties. To evaluate the structural requirement for this inhibitory activity, we examined the effects of various derivatives of sulphoglycolipids, some of which were prepared by deacylation with sphingolipid ...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1010988709764
更新日期:2000-11-01 00:00:00
abstract::Altered glycosylation is a universal feature of cancer cells and altered glycans can help cancer cells escape immune surveillance, facilitate tumor invasion, and increase malignancy. The goal of this study was to identify specific glycoenzymes, which could distinguish prostate cancer cells from normal prostatic cells....
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-012-9428-8
更新日期:2012-10-01 00:00:00
abstract::Gastric carcinoma is a major cause of cancer death worldwide and, like most human cancers, probably develops after environmental insults acting on normal individuals and/or individuals with increased genetic susceptibility. Mucins are attractive molecules to study the relationship between genetics and environment beca...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1018573201347
更新日期:1997-01-01 00:00:00
abstract::Glycans serve as important regulators of antibody activities and half-lives. IgE is the most heavily glycosylated antibody, but in comparison to other antibodies little is known about its glycan structure function relationships. We therefore describe the site specific IgE glycosylation from a patient with a novel hype...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-015-9638-y
更新日期:2016-06-01 00:00:00
abstract::We have previously shown that murine resident peritoneal macrophages (PEMs) are activated in response to uptake of oligomannose-coated liposomes (OMLs), leading to production of interleukin (IL)-12. To understand the mechanism of activation of PEMs by OMLs, in the present study we investigated the role of a mannose-bi...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-010-9298-x
更新日期:2010-07-01 00:00:00
abstract::Homology searches indicated that up to five class I α-mannosidases (glycohydrolase family 47) and eight class II α-mannosidases (glycohydrolase family 38) are encoded by the fruitfly (Drosophila melanogaster) genome. Selected example mannosidases were expressed in secreted form using the yeast Pichia pastoris. A numbe...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-013-9495-5
更新日期:2013-12-01 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 complex microenvironment that surrounds hematopoietic stem cells (HSCs) in the bone marrow niche involves different coordinated signaling pathways. The stem cells establish permanent interactions with distinct cell types such as mesenchymal stromal cells, osteoblasts, osteoclasts or endothelial cells and with secr...
journal_title:Glycoconjugate journal
pub_type: 杂志文章,评审
doi:10.1007/s10719-017-9773-8
更新日期:2017-06-01 00:00:00
abstract::Diabetic mellitus is attended by the development of endothelial dysfunction which is suggested to be accompanied with a chronic low-degree of inflammation. During a chronic hepatic inflammatory response, specific changes in glycosylation of the acute phase protein alpha1-acid glycoprotein (AGP) can be detected. In thi...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1023/a:1012412908983
更新日期:2001-03-01 00:00:00
abstract::A group of fluorescent statistical glycopolymers, prepared via reversible addition-fragmentation chain-transfer (RAFT)-based polymerizations, were successfully employed in lectin-mediated bacterial binding studies. The resultant glycopolymers contained three different monomers: N-(2-hydroxyethyl) acrylamide (HEAA), N-...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-013-9508-4
更新日期:2014-02-01 00:00:00
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 e...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/s10719-011-9352-3
更新日期:2011-12-01 00:00:00
abstract::By employing a bovine UDP-N-acetylgalactosamine: polypeptide N-acetylgalactosaminyl transferase (O-GalNAc transferase) cDNA as a probe, we isolated four overlapping cDNAs from a porcine lung cDNA library. Both the nucleotide sequence of the porcine cDNA and the predicted primary structure of the protein (559 amino aci...
journal_title:Glycoconjugate journal
pub_type: 杂志文章
doi:10.1007/BF00731244
更新日期:1995-12-01 00:00:00