Conformational studies of oligosaccharides and glycopeptides: complementarity of NMR, X-ray crystallography, and molecular modelling.

PubWeight™: 2.02‹?› | Rank: Top 2%

🔗 View Article (PMID 11841247)

Published in Chem Rev on February 01, 2002

Authors

Mark R Wormald1, Andrei J Petrescu, Ya-Lan Pao, Ann Glithero, Tim Elliott, Raymond A Dwek

Author Affiliations

1: Oxford Glycobiology Institute, Department of Biochemistry, Oxford University, South Parks Road, Oxford OX1 3QU, United Kingdom. mark@glycob.ox.ac.uk

Articles citing this

GLYCAM06: a generalizable biomolecular force field. Carbohydrates. J Comput Chem (2008) 4.51

Carbohydrate vaccines: developing sweet solutions to sticky situations? Nat Rev Drug Discov (2010) 2.69

A systematic approach to protein glycosylation analysis: a path through the maze. Nat Chem Biol (2010) 2.30

Carbohydrate Structure Suite (CSS): analysis of carbohydrate 3D structures derived from the PDB. Nucleic Acids Res (2005) 1.84

High throughput isolation and glycosylation analysis of IgG-variability and heritability of the IgG glycome in three isolated human populations. Mol Cell Proteomics (2011) 1.70

Promiscuous glycan site recognition by antibodies to the high-mannose patch of gp120 broadens neutralization of HIV. Sci Transl Med (2014) 1.60

Intervening with urinary tract infections using anti-adhesives based on the crystal structure of the FimH-oligomannose-3 complex. PLoS One (2008) 1.54

The core trisaccharide of an N-linked glycoprotein intrinsically accelerates folding and enhances stability. Proc Natl Acad Sci U S A (2009) 1.54

maternally expressed gene1 Is a novel maize endosperm transfer cell-specific gene with a maternal parent-of-origin pattern of expression. Plant Cell (2004) 1.45

Polysaccharide mimicry of the epitope of the broadly neutralizing anti-HIV antibody, 2G12, induces enhanced antibody responses to self oligomannose glycans. Glycobiology (2010) 1.39

Complement regulation at the molecular level: the structure of decay-accelerating factor. Proc Natl Acad Sci U S A (2004) 1.17

Solute-induced retardation of water dynamics probed directly by terahertz spectroscopy. Proc Natl Acad Sci U S A (2006) 1.13

The O-glycosylated linker from the Trichoderma reesei Family 7 cellulase is a flexible, disordered protein. Biophys J (2010) 1.11

Analysis and validation of carbohydrate three-dimensional structures. Acta Crystallogr D Biol Crystallogr (2009) 1.08

Cell signaling, post-translational protein modifications and NMR spectroscopy. J Biomol NMR (2012) 1.06

Semi-automated identification of N-Glycopeptides by hydrophilic interaction chromatography, nano-reverse-phase LC-MS/MS, and glycan database search. J Proteome Res (2012) 1.04

Function and 3D structure of the N-glycans on glycoproteins. Int J Mol Sci (2012) 1.04

Discovery of novel inhibitors of a disintegrin and metalloprotease 17 (ADAM17) using glycosylated and non-glycosylated substrates. J Biol Chem (2012) 1.02

CHARMM Additive All-Atom Force Field for Phosphate and Sulfate Linked to Carbohydrates. J Chem Theory Comput (2011) 1.00

The power of coarse graining in biomolecular simulations. Wiley Interdiscip Rev Comput Mol Sci (2014) 1.00

Glycoconjugate Data Bank: Structures--an annotated glycan structure database and N-glycan primary structure verification service. Nucleic Acids Res (2007) 0.99

Techniques and tactics used in determining the structure of the trimeric ebolavirus glycoprotein. Acta Crystallogr D Biol Crystallogr (2009) 0.99

Glycan fragment database: a database of PDB-based glycan 3D structures. Nucleic Acids Res (2012) 0.96

A 3D-structural model of unsulfated chondroitin from high-field NMR: 4-sulfation has little effect on backbone conformation. Carbohydr Res (2009) 0.95

Reconciling solvent effects on rotamer populations in carbohydrates - A joint MD and NMR analysis. Can J Chem (2006) 0.95

Recent advances in segmental isotope labeling of proteins: NMR applications to large proteins and glycoproteins. J Biomol NMR (2009) 0.95

Modeling of the N-glycosylated transferrin receptor suggests how transferrin binding can occur within the surface coat of Trypanosoma brucei. PLoS Pathog (2012) 0.94

Total synthesis of the α-subunit of human glycoprotein hormones: toward fully synthetic homogeneous human follicle-stimulating hormone. J Am Chem Soc (2012) 0.93

Polarizable empirical force field for hexopyranose monosaccharides based on the classical Drude oscillator. J Phys Chem B (2014) 0.93

Context-dependent effects of asparagine glycosylation on Pin WW folding kinetics and thermodynamics. J Am Chem Soc (2010) 0.93

Glycosylation of the enhanced aromatic sequon is similarly stabilizing in three distinct reverse turn contexts. Proc Natl Acad Sci U S A (2011) 0.92

Structural diversity and changes in conformational equilibria of biantennary complex-type N-glycans in water revealed by replica-exchange molecular dynamics simulation. Biophys J (2011) 0.90

Influence of solvent and intramolecular hydrogen bonding on the conformational properties of o-linked glycopeptides. J Phys Chem B (2011) 0.89

Restricted N-glycan conformational space in the PDB and its implication in glycan structure modeling. PLoS Comput Biol (2013) 0.89

Conformational properties of α- or β-(1→6)-linked oligosaccharides: Hamiltonian replica exchange MD simulations and NMR experiments. J Phys Chem B (2014) 0.88

N-glycosylation of enhanced aromatic sequons to increase glycoprotein stability. Biopolymers (2012) 0.86

N-linked oligosaccharides play a role in disulphide-dependent dimerization of intestinal mucin Muc2. Biochem J (2003) 0.85

Reverse orthogonal strategy for oligosaccharide synthesis. Chem Commun (Camb) (2011) 0.84

Shaping up for structural glycomics: a predictive protocol for oligosaccharide conformational analysis applied to N-linked glycans. Carbohydr Res (2013) 0.84

Structure of dipeptides having N-terminal selenocysteine residues: a DFT study in gas and aqueous phase. J Mol Model (2013) 0.83

Extending RosettaDock with water, sugar, and pH for prediction of complex structures and affinities for CAPRI rounds 20-27. Proteins (2013) 0.83

Investigations of dipeptide structures containing pyrrolysine as N-terminal residues: a DFT study in gas and aqueous phase. J Mol Model (2013) 0.82

Structural monitoring of oligosaccharides through 13C enrichment and NMR observation of acetyl groups. Biophys J (2006) 0.82

In vitro mannose trimming property of human ER α-1,2 mannosidase I. Glycoconj J (2011) 0.82

Preferred conformations of N-glycan core pentasaccharide in solution and in glycoproteins. Glycobiology (2015) 0.81

Glycan analysis of therapeutic glycoproteins. MAbs (2015) 0.81

Application of Metabolic 13C Labeling in Conjunction with High-Field Nuclear Magnetic Resonance Spectroscopy for Comparative Conformational Analysis of High Mannose-Type Oligosaccharides. Biomolecules (2013) 0.80

A tool for the prediction of structures of complex sugars. J Biomol NMR (2008) 0.80

Total synthesis of glycosylated proteins. Top Curr Chem (2015) 0.78

The effect of glycosylation on interparticle interactions and dimensions of native and denatured phytase. Biophys J (2009) 0.78

DFT studies on the intrinsic conformational properties of non-ionic pyrrolysine in gas phase. J Mol Model (2013) 0.78

Interrelationship of steric stabilization and self-crowding of a glycosylated protein. Biophys J (2009) 0.76

Atomic visualization of a flipped-back conformation of bisected glycans bound to specific lectins. Sci Rep (2016) 0.76

All-Atom Internal Coordinate Mechanics (ICM) Force Field for Hexopyranoses and Glycoproteins. J Chem Theory Comput (2015) 0.75

'Naked' and hydrated conformers of the conserved core pentasaccharide of N-linked glycoproteins and its building blocks. J Am Chem Soc (2013) 0.75

Studying Lactoferrin N-Glycosylation. Int J Mol Sci (2017) 0.75

Nearest-neighbor interactions and their influence on the structural aspects of dipeptides. Biochem Res Int (2013) 0.75

Glyco-epitope Diversity: An Evolving Area of Glycomics Research and Biomarker Discovery. J Proteomics Bioinform (2014) 0.75

Evidence for a second peptide cleavage in the C-terminal domain of rodent intestinal mucin Muc3. Biochem J (2004) 0.75

Comprehensive N-Glycan Profiling of Avian Immunoglobulin Y. PLoS One (2016) 0.75

A carbohydrate-anion recognition system in aprotic solvents. Chem Asian J (2014) 0.75

Zwitterionic conformers of pyrrolysine and their interactions with metal ions--a theoretical study. J Mol Model (2013) 0.75

Effects of varying the 6-position oxidation state of hexopyranoses: a systematic comparative computational analysis of 48 monosaccharide stereoisomers. J Mol Model (2017) 0.75

Insights from NMR Spectroscopy into the Conformational Properties of Man-9 and Its Recognition by Two HIV Binding Proteins. Chembiochem (2017) 0.75

Conformational Populations of β-(1→4) O-Glycosidic Linkages Using Redundant NMR J-Couplings and Circular Statistics. J Phys Chem B (2017) 0.75

Articles by these authors

(truncated to the top 100)

The broadly neutralizing anti-human immunodeficiency virus type 1 antibody 2G12 recognizes a cluster of alpha1-->2 mannose residues on the outer face of gp120. J Virol (2002) 7.82

Antibody domain exchange is an immunological solution to carbohydrate cluster recognition. Science (2003) 6.68

The impact of glycosylation on the biological function and structure of human immunoglobulins. Annu Rev Immunol (2007) 4.96

The amount of recycled crust in sources of mantle-derived melts. Science (2007) 3.93

Biochemistry and molecular biology of gelatinase B or matrix metalloproteinase-9 (MMP-9). Crit Rev Biochem Mol Biol (2002) 3.53

Statistical analysis of the protein environment of N-glycosylation sites: implications for occupancy, structure, and folding. Glycobiology (2003) 3.19

Exploiting the defensive sugars of HIV-1 for drug and vaccine design. Nature (2007) 3.01

Proposal for a standard system for drawing structural diagrams of N- and O-linked carbohydrates and related compounds. Proteomics (2009) 2.93

Comparison of the methods for profiling glycoprotein glycans--HUPO Human Disease Glycomics/Proteome Initiative multi-institutional study. Glycobiology (2007) 2.71

Use of targeted glycoproteomics to identify serum glycoproteins that correlate with liver cancer in woodchucks and humans. Proc Natl Acad Sci U S A (2005) 2.70

The hepatitis C virus p7 protein forms an ion channel that is inhibited by long-alkyl-chain iminosugar derivatives. Proc Natl Acad Sci U S A (2003) 2.64

Structural characterization of the 1918 influenza virus H1N1 neuraminidase. J Virol (2008) 2.63

Stem cells act through multiple mechanisms to benefit mice with neurodegenerative metabolic disease. Nat Med (2007) 2.57

Envelope glycans of immunodeficiency virions are almost entirely oligomannose antigens. Proc Natl Acad Sci U S A (2010) 2.51

Infantile-onset symptomatic epilepsy syndrome caused by a homozygous loss-of-function mutation of GM3 synthase. Nat Genet (2004) 2.45

Ovarian cancer is associated with changes in glycosylation in both acute-phase proteins and IgG. Glycobiology (2007) 2.45

Glycoprotein structural genomics: solving the glycosylation problem. Structure (2007) 2.40

Origin of nucleosynthetic isotope heterogeneity in the solar protoplanetary disk. Science (2009) 2.17

Contrasting IgG structures reveal extreme asymmetry and flexibility. J Mol Biol (2002) 2.10

The mannose receptor mediates dengue virus infection of macrophages. PLoS Pathog (2008) 2.09

Optimization of the MHC class I peptide cargo is dependent on tapasin. Immunity (2002) 2.02

The glycan shield of HIV is predominantly oligomannose independently of production system or viral clade. PLoS One (2011) 1.95

HPLC-based analysis of serum N-glycans on a 96-well plate platform with dedicated database software. Anal Biochem (2007) 1.92

Altered glycosylation pattern allows the distinction between prostate-specific antigen (PSA) from normal and tumor origins. Glycobiology (2003) 1.91

Depletion of CD25+ regulatory cells uncovers immune responses to shared murine tumor rejection antigens. Eur J Immunol (2002) 1.88

Reversible infertility in male mice after oral administration of alkylated imino sugars: a nonhormonal approach to male contraception. Proc Natl Acad Sci U S A (2002) 1.88

Implications for invariant natural killer T cell ligands due to the restricted presence of isoglobotrihexosylceramide in mammals. Proc Natl Acad Sci U S A (2007) 1.84

Emerging principles for the therapeutic exploitation of glycosylation. Science (2014) 1.83

Antiviral effects of an iminosugar derivative on flavivirus infections. J Virol (2002) 1.80

Peptide antagonism as a mechanism for NK cell activation. Proc Natl Acad Sci U S A (2010) 1.72

Secretory IgA N- and O-glycans provide a link between the innate and adaptive immune systems. J Biol Chem (2003) 1.68

Tungsten isotope evidence that mantle plumes contain no contribution from the Earth's core. Nature (2004) 1.66

Storage solutions: treating lysosomal disorders of the brain. Nat Rev Neurosci (2005) 1.65

GlycoBase and autoGU: tools for HPLC-based glycan analysis. Bioinformatics (2008) 1.64

Different glycan structures in prostate-specific antigen from prostate cancer sera in relation to seminal plasma PSA. Glycobiology (2005) 1.60

A strategy to reveal potential glycan markers from serum glycoproteins associated with breast cancer progression. Glycobiology (2008) 1.55

Assembly and antigen-presenting function of MHC class I molecules in cells lacking the ER chaperone calreticulin. Immunity (2002) 1.54

Lymphoblastoid cells express HLA-B27 homodimers both intracellularly and at the cell surface following endosomal recycling. Eur J Immunol (2003) 1.53

Novel serum biomarker candidates for liver fibrosis in hepatitis C patients. Clin Chem (2007) 1.52

Genes contributing to prion pathogenesis. J Gen Virol (2008) 1.51

Treatment with miglustat reverses the lipid-trafficking defect in Niemann-Pick disease type C. Neurobiol Dis (2004) 1.50

Structural and quantitative analysis of N-linked glycans by matrix-assisted laser desorption ionization and negative ion nanospray mass spectrometry. Anal Biochem (2008) 1.49

Antiviral effects of amantadine and iminosugar derivatives against hepatitis C virus. Hepatology (2007) 1.49

Tapasin enhances MHC class I peptide presentation according to peptide half-life. Proc Natl Acad Sci U S A (2004) 1.49

Human serum IgM glycosylation: identification of glycoforms that can bind to mannan-binding lectin. J Biol Chem (2005) 1.47

The 3-dimensional structure of a hepatitis C virus p7 ion channel by electron microscopy. Proc Natl Acad Sci U S A (2009) 1.44

Detailed structural analysis of N-glycans released from glycoproteins in SDS-PAGE gel bands using HPLC combined with exoglycosidase array digestions. Methods Mol Biol (2006) 1.43

Analysis of fluorescently labeled glycosphingolipid-derived oligosaccharides following ceramide glycanase digestion and anthranilic acid labeling. Anal Biochem (2004) 1.42

Reactivity-based one-pot synthesis of oligomannoses: defining antigens recognized by 2G12, a broadly neutralizing anti-HIV-1 antibody. Angew Chem Int Ed Engl (2004) 1.41

Inhibition of mammalian glycan biosynthesis produces non-self antigens for a broadly neutralising, HIV-1 specific antibody. J Mol Biol (2007) 1.41

Molecular mechanism of lipopeptide presentation by CD1a. Immunity (2005) 1.41

Polysaccharide mimicry of the epitope of the broadly neutralizing anti-HIV antibody, 2G12, induces enhanced antibody responses to self oligomannose glycans. Glycobiology (2010) 1.39

Differential proteome analysis of TRAP-activated platelets: involvement of DOK-2 and phosphorylation of RGS proteins. Blood (2003) 1.39

The hemopexin and O-glycosylated domains tune gelatinase B/MMP-9 bioavailability via inhibition and binding to cargo receptors. J Biol Chem (2006) 1.36

Naturally occurring ERAP1 haplotypes encode functionally distinct alleles with fine substrate specificity. J Immunol (2013) 1.34

A glycoconjugate antigen based on the recognition motif of a broadly neutralizing human immunodeficiency virus antibody, 2G12, is immunogenic but elicits antibodies unable to bind to the self glycans of gp120. J Virol (2008) 1.34

Increased levels of galactose-deficient anti-Gal immunoglobulin G in the sera of hepatitis C virus-infected individuals with fibrosis and cirrhosis. J Virol (2007) 1.33

Detailed glycan analysis of serum glycoproteins of patients with congenital disorders of glycosylation indicates the specific defective glycan processing step and provides an insight into pathogenesis. Glycobiology (2003) 1.32

Imino sugar inhibitors for treating the lysosomal glycosphingolipidoses. Glycobiology (2005) 1.31

Glycosylation changes on serum glycoproteins in ovarian cancer may contribute to disease pathogenesis. Dis Markers (2008) 1.27

An analytical and structural database provides a strategy for sequencing O-glycans from microgram quantities of glycoproteins. Anal Biochem (2002) 1.25

The tungsten isotopic composition of the Earth's mantle before the terminal bombardment. Nature (2011) 1.23

Calreticulin-dependent recycling in the early secretory pathway mediates optimal peptide loading of MHC class I molecules. EMBO J (2009) 1.23

Accumulation of glycosphingolipids in Niemann-Pick C disease disrupts endosomal transport. J Biol Chem (2004) 1.22

Mannan binding lectin and its interaction with immunoglobulins in health and in disease. Immunol Lett (2006) 1.21

Towards complete analysis of the platelet proteome. Proteomics (2002) 1.21

Crystallographic, thermodynamic, and molecular modeling studies of the mode of binding of oligosaccharides to the potent antiviral protein griffithsin. Proteins (2007) 1.20

Human follicular lymphoma cells contain oligomannose glycans in the antigen-binding site of the B-cell receptor. J Biol Chem (2006) 1.19

Inhibition of hybrid- and complex-type glycosylation reveals the presence of the GlcNAc transferase I-independent fucosylation pathway. Glycobiology (2006) 1.18

Glucosylceramide modulates membrane traffic along the endocytic pathway. J Lipid Res (2002) 1.17

Function and glycosylation of plant-derived antiviral monoclonal antibody. Proc Natl Acad Sci U S A (2003) 1.16

The O-linked glycosylation of secretory/shed MUC1 from an advanced breast cancer patient's serum. Glycobiology (2008) 1.15

NSAIDs increase survival in the Sandhoff disease mouse: synergy with N-butyldeoxynojirimycin. Ann Neurol (2004) 1.15

The carbohydrate epitope of the neutralizing anti-HIV-1 antibody 2G12. Adv Exp Med Biol (2003) 1.15

The oxidoreductase ERp57 efficiently reduces partially folded in preference to fully folded MHC class I molecules. EMBO J (2002) 1.14

Retracted Lectin-deficient calreticulin retains full functionality as a chaperone for class I histocompatibility molecules. Mol Biol Cell (2008) 1.14

Structural aspects of glycomes with a focus on N-glycosylation and glycoprotein folding. Curr Opin Struct Biol (2006) 1.14

Glycosylation of serum ribonuclease 1 indicates a major endothelial origin and reveals an increase in core fucosylation in pancreatic cancer. Glycobiology (2007) 1.13

Afamin is a novel human vitamin E-binding glycoprotein characterization and in vitro expression. J Proteome Res (2005) 1.13

EUROCarbDB: An open-access platform for glycoinformatics. Glycobiology (2010) 1.13

The glycosylation of human serum IgD and IgE and the accessibility of identified oligomannose structures for interaction with mannan-binding lectin. J Immunol (2004) 1.12

Invariant NKT cells promote CD8+ cytotoxic T cell responses by inducing CD70 expression on dendritic cells. J Immunol (2008) 1.12

Soluble CD36 ectodomain binds negatively charged diacylglycerol ligands and acts as a co-receptor for TLR2. PLoS One (2009) 1.12

ERp57 does not require interactions with calnexin and calreticulin to promote assembly of class I histocompatibility molecules, and it enhances peptide loading independently of its redox activity. J Biol Chem (2009) 1.11

Sugar-mediated ligand-receptor interactions in the immune system. Trends Biotechnol (2004) 1.09

Antigenic mimicry of the HIV envelope by AIDS-associated pathogens. AIDS (2008) 1.08

Glycosylation of human pancreatic ribonuclease: differences between normal and tumor states. Glycobiology (2002) 1.08

A global proteomics approach identifies novel phosphorylated signaling proteins in GPVI-activated platelets: involvement of G6f, a novel platelet Grb2-binding membrane adapter. Proteomics (2006) 1.08

Extensive analysis of the human platelet proteome by two-dimensional gel electrophoresis and mass spectrometry. Proteomics (2004) 1.07

In planta secretion of a calreticulin by migratory and sedentary stages of root-knot nematode. Mol Plant Microbe Interact (2005) 1.06

Glycosylation and the complement system. Chem Rev (2002) 1.06

The characterization of the invasion phenotype of uveal melanoma tumour cells shows the presence of MUC18 and HMG-1 metastasis markers and leads to the identification of DJ-1 as a potential serum biomarker. Int J Cancer (2006) 1.05

Glucosylated free oligosaccharides are biomarkers of endoplasmic- reticulum alpha-glucosidase inhibition. Biochem J (2008) 1.05

Improved outcome of N-butyldeoxygalactonojirimycin-mediated substrate reduction therapy in a mouse model of Sandhoff disease. Neurobiol Dis (2004) 1.04

An iminosugar with potent inhibition of dengue virus infection in vivo. Antiviral Res (2013) 1.04

Polyunsaturated liposomes are antiviral against hepatitis B and C viruses and HIV by decreasing cholesterol levels in infected cells. Proc Natl Acad Sci U S A (2010) 1.03

Accumulation of glucosylceramide in murine testis, caused by inhibition of beta-glucosidase 2: implications for spermatogenesis. J Biol Chem (2007) 1.03

Activation state and intracellular trafficking contribute to the repertoire of endogenous glycosphingolipids presented by CD1d [corrected]. Proc Natl Acad Sci U S A (2010) 1.03

Chromophore structure in the photocycle of the cyanobacterial phytochrome Cph1. Biophys J (2006) 1.03

Recovery of intact 2-aminobenzamide-labeled O-glycans released from glycoproteins by hydrazinolysis. Anal Biochem (2002) 1.01