Glycosyldisulfides from dynamic combinatorial libraries as O-glycoside mimetics for plant and endogenous lectins: their reactivities in solid-phase and cell assays and conformational analysis by molecular dynamics simulations.

[1]  R. Schmidt Strategies for the Chemical Synthesis of Glycoconjugates , 2008 .

[2]  Roger A. Laine,et al.  The Information‐Storing Potential of the Sugar Code , 2008 .

[3]  Hans-Joachim Gabius,et al.  Interaction profile of galectin-5 with free saccharides and mammalian glycoproteins: probing its fine specificity and the effect of naturally clustered ligand presentation. , 2006, Glycobiology.

[4]  H. Gabius,et al.  Branching mode in complex-type triantennary N-glycans as regulatory element of their ligand properties. , 2006, Biochimica et Biophysica Acta.

[5]  H. Gabius,et al.  Monomer/dimer equilibrium of the AB-type lectin from mistletoe enables combination of toxin/agglutinin activities in one protein: analysis of native and citraconylated proteins by ultracentrifugation/gel filtration and cell biological consequences of dimer destabilization. , 2005, Glycobiology.

[6]  O. Ramström,et al.  Solvent-dependent, kinetically controlled stereoselective synthesis of 3- and 4-thioglycosides. , 2005, The Journal of organic chemistry.

[7]  T. Aastrup,et al.  Redox-responsive and calcium-dependent switching of glycosyldisulfide interactions with Concanavalin A. , 2005, Bioorganic & medicinal chemistry letters.

[8]  Kai Simons,et al.  Galectin-4 and sulfatides in apical membrane trafficking in enterocyte-like cells , 2005, The Journal of cell biology.

[9]  S. Olofsson,et al.  Glycoconjugate glycans as viral receptors , 2005, Annals of medicine.

[10]  H. Gabius,et al.  Introduction of extended LEC14‐type branching into core‐fucosylated biantennary N‐glycan , 2005, The FEBS journal.

[11]  Albert J R Heck,et al.  Determination of structural and functional overlap/divergence of five proto‐type galectins by analysis of the growth‐regulatory interaction with ganglioside GM1 in silico and in vitro on human neuroblastoma cells , 2005, International journal of cancer.

[12]  P. Seeberger,et al.  Carbohydrate diversity: synthesis of glycoconjugates and complex carbohydrates. , 2004, Current opinion in biotechnology.

[13]  Yigal M. Pinto,et al.  Galectin-3 Marks Activated Macrophages in Failure-Prone Hypertrophied Hearts and Contributes to Cardiac Dysfunction , 2004, Circulation.

[14]  H. Gabius,et al.  Glycomic profiling of developmental changes in bovine testis by lectin histochemistry and further analysis of the most prominent alteration on the level of the glycoproteome by lectin blotting and lectin affinity chromatography. , 2004, Histology and histopathology.

[15]  B. Wiedenmann,et al.  Human Galectin-2: Novel Inducer of T Cell Apoptosis with Distinct Profile of Caspase Activation1 , 2004, The Journal of Immunology.

[16]  Richard D. Cummings,et al.  LacdiNAc-Glycans Constitute a Parasite Pattern for Galectin-3-Mediated Immune Recognition1 , 2004, The Journal of Immunology.

[17]  Shinsuke Sando,et al.  A facile route to dynamic glycopeptide libraries based on disulfide-linked sugar-peptide coupling. , 2004, Bioorganic & medicinal chemistry letters.

[18]  B. Rotblat,et al.  Galectin-1(L11A) predicted from a computed galectin-1 farnesyl-binding pocket selectively inhibits Ras-GTP. , 2004, Cancer research.

[19]  J. Lehn,et al.  Dynamic combinatorial carbohydrate libraries: probing the binding site of the concanavalin A lectin. , 2004, Chemistry.

[20]  Hans-Joachim Gabius,et al.  Effects of polyvalency of glycotopes and natural modifications of human blood group ABH/Lewis sugars at the Galbeta1-terminated core saccharides on the binding of domain-I of recombinant tandem-repeat-type galectin-4 from rat gastrointestinal tract (G4-N). , 2004, Biochimie.

[21]  H. Gabius,et al.  Galectin-3 Precipitates as a Pentamer with Synthetic Multivalent Carbohydrates and Forms Heterogeneous Cross-linked Complexes* , 2004, Journal of Biological Chemistry.

[22]  P. Garnier,et al.  Glyco-SeS: selenenylsulfide-mediated protein glycoconjugation--a new strategy in post-translational modification. , 2004, Angewandte Chemie.

[23]  V. Wittmann,et al.  Spatial screening of cyclic neoglycopeptides: identification of polyvalent wheat-germ agglutinin ligands. , 2004, Angewandte Chemie.

[24]  Jesús Jiménez-Barbero,et al.  Unique conformer selection of human growth-regulatory lectin galectin-1 for ganglioside GM1 versus bacterial toxins. , 2003, Biochemistry.

[25]  Fu-Tong Liu,et al.  New aspects of galectin functionality in nuclei of cultured bone marrow stromal and epidermal cells: biotinylated galectins as tool to detect specific binding sites , 2003, Biology of the cell.

[26]  A. Tonevitsky,et al.  Crystal structure at 3 A of mistletoe lectin I, a dimeric type-II ribosome-inactivating protein, complexed with galactose. , 2003, European journal of biochemistry.

[27]  K Kayser,et al.  Combined analysis of tumor growth pattern and expression of endogenous lectins as a prognostic tool in primary testicular cancer and its lung metastases. , 2003, Histology and histopathology.

[28]  A. Hoeflich,et al.  Tumor galectinology: Insights into the complex network of a family of endogenous lectins , 2003, Glycoconjugate Journal.

[29]  R. Kiss,et al.  Refined prognostic evaluation in colon carcinoma using immunohistochemical galectin fingerprinting , 2003, Cancer.

[30]  J. Lowe,et al.  Role of glycosylation in development. , 2003, Annual review of biochemistry.

[31]  A. M. Wu,et al.  Fine specificity of domain-I of recombinant tandem-repeat-type galectin-4 from rat gastrointestinal tract (G4-N). , 2002, The Biochemical journal.

[32]  Y. Kloog,et al.  Galectin-1 Augments Ras Activation and Diverts Ras Signals to Raf-1 at the Expense of Phosphoinositide 3-Kinase* , 2002, The Journal of Biological Chemistry.

[33]  H. Kunz,et al.  Synthesis of tumor-associated glycopeptide antigens. , 2002, Bioorganic & medicinal chemistry.

[34]  J. Lehn,et al.  Chemical biology of dynamic combinatorial libraries. , 2002, Biochimica et biophysica acta.

[35]  Hans-Joachim Gabius,et al.  The sugar code: functional lectinomics. , 2002, Biochimica et biophysica acta.

[36]  C. F. Brewer,et al.  Binding and cross-linking properties of galectins. , 2002 .

[37]  R. Kiss,et al.  Galectin‐1 Modulates Human Glioblastoma Cell Migration into the Brain Through Modifications to the Actin Cytoskeleton and Levels of Expression of Small GTPases , 2002, Journal of neuropathology and experimental neurology.

[38]  J. García,et al.  Conformational selection of glycomimetics at enzyme catalytic sites: experimental demonstration of the binding of distinct high-energy distorted conformations of C-, S-, and O-glycosides by E. Coli beta-galactosidases. , 2002, Journal of the American Chemical Society.

[39]  P. V. Balaji,et al.  Molecular dynamics simulations of alpha2 --> 8-linked disialoside: conformational analysis and implications for binding to proteins. , 2002, Biopolymers.

[40]  Hans-Joachim Gabius,et al.  Glycosciences: Status and Perspectives , 2002 .

[41]  Klaus Kayser,et al.  Structure-activity profiles of complex biantennary glycans with core fucosylation and with/without additional alpha 2,3/alpha 2,6 sialylation: synthesis of neoglycoproteins and their properties in lectin assays, cell binding, and organ uptake. , 2002, Journal of medicinal chemistry.

[42]  J. Jiménez-Barbero,et al.  NMR investigations of protein-carbohydrate interactions: insights into the topology of the bound conformation of a lactose isomer and beta-galactosyl xyloses to mistletoe lectin and galectin-1. , 2001, Biochimica et biophysica acta.

[43]  H Kaltner,et al.  Negative Regulation of Neuroblastoma Cell Growth by Carbohydrate-dependent Surface Binding of Galectin-1 and Functional Divergence from Galectin-3* , 2001, The Journal of Biological Chemistry.

[44]  A. M. Wu,et al.  Carbohydrate specificity of a galectin from chicken liver (CG-16). , 2001, The Biochemical journal.

[45]  H. Gabius,et al.  Plant lectins: Occurrence, biochemistry, functions and applications , 2001, Glycoconjugate Journal.

[46]  A. Surolia,et al.  Thermodynamic analysis of the binding of galactose and poly‐N‐acetyllactosamine derivatives to human galectin‐3 , 2001, FEBS letters.

[47]  P. Marker,et al.  fucosyltransferase1 and H-type complex carbohydrates modulate epithelial cell proliferation during prostatic branching morphogenesis. , 2001, Developmental biology.

[48]  R. Kiss,et al.  Galectin‐1 is highly expressed in human gliomas with relevance for modulation of invasion of tumor astrocytes into the brain parenchyma , 2001, Glia.

[49]  L. Delbaere,et al.  The 2.2 A resolution structure of the O(H) blood-group-specific lectin I from Ulex europaeus. , 2000, Journal of molecular biology.

[50]  N V Bovin,et al.  Endogenous lectins as targets for drug delivery. , 2000, Advanced drug delivery reviews.

[51]  L. Amzel,et al.  Soluble β‐galactosyl‐binding lectin (galectin) from toad ovary: Crystallographic studies of two protein‐sugar complexes , 2000, Proteins.

[52]  H. Gabius,et al.  Lectin-Mediated Drug Targeting: Selection of Valency, Sugar Type (Gal/Lac), and Spacer Length for Cluster Glycosides as Parameters to Distinguish Ligand Binding to C-Type Asialoglycoprotein Receptors and Galectins , 2000, Pharmaceutical Research.

[53]  St Hilaire PM,et al.  Glycopeptide and Oligosaccharide Libraries. , 1999, Angewandte Chemie.

[54]  A. Surolia,et al.  Microcalorimetric indications for ligand binding as a function of the protein for galactoside-specific plant and avian lectins. , 1999, Biochimica et biophysica acta.

[55]  K. Kayser,et al.  Galectins-1 and -3 and their ligands in tumor biology , 1999, Journal of Cancer Research and Clinical Oncology.

[56]  Tomikazu Sasaki,et al.  Iron(II)-Assisted Assembly of Trivalent GalNAc Clusters and Their Interactions with GalNAc-Specific Lectins , 1999 .

[57]  H. Gabius,et al.  Eukaryotic glycosylation: whim of nature or multipurpose tool? , 1999, Cellular and Molecular Life Sciences CMLS.

[58]  L M Amzel,et al.  Thermodynamics of bovine spleen galectin-1 binding to disaccharides: correlation with structure and its effect on oligomerization at the denaturation temperature. , 1998, Biochemistry.

[59]  H Kaltner,et al.  Conformer selection and differential restriction of ligand mobility by a plant lectin--conformational behaviour of Galbeta1-3GlcNAcbeta1-R, Galbeta1-3GalNAcbeta1-R and Galbeta1-2Galbeta1-R' in the free state and complexed with galactoside-specific mistletoe lectin as revealed by random-walk and conf , 1998, European journal of biochemistry.

[60]  A. Fernández-Mayoralas,et al.  Conformational differences between Fuc(alpha 1-3) GlcNAc and its thioglycoside analogue. , 1998, Carbohydrate research.

[61]  Tomikazu Sasaki,et al.  A self-adjusting carbohydrate ligand for GalNAc specific lectins , 1997 .

[62]  H Kaltner,et al.  Further refinement of the description of the ligand‐binding characteristics for the galactoside‐binding mistletoe lectin, a plant agglutinin with immunomodulatory potency , 1997, Journal of molecular recognition : JMR.

[63]  H. Kondo,et al.  Selectin-ligand interactions revealed by molecular dynamics simulation in solution. , 1997, Journal of medicinal chemistry.

[64]  H. Kondo,et al.  Studies on selectin blockers. 2. Novel selectin blocker as potential therapeutics for inflammatory disorders. , 1996, Journal of medicinal chemistry.

[65]  A. Surolia,et al.  Energetics of carbohydrate binding by a 14 kDa S-type mammalian lectin. , 1995, The Biochemical journal.

[66]  J. Sacchettini,et al.  X-ray crystal structure of the soybean agglutinin cross-linked with a biantennary analog of the blood group I carbohydrate antigen. , 1995, Biochemistry.

[67]  H. Gabius,et al.  The sugar-combining area of the galactose-specific toxic lectin of mistletoe extends beyond the terminal sugar residue: comparison with a homologous toxic lectin, ricin. , 1994, Carbohydrate research.

[68]  S. Gellman,et al.  Complexation of hexosammonium ions: evidence for contributions from OH.cntdot..cntdot..cntdot.OH hydrogen bonds in a hydroxylic medium , 1993 .

[69]  J. Duus,et al.  Conformational equilibria of 4-thiomaltose and nitrogen analogues of maltose in aqueous solutions. , 1992, Carbohydrate research.

[70]  H. Gabius,et al.  Ligand binding characteristics of the major mistletoe lectin. , 1992, The Journal of biological chemistry.

[71]  S. Joshi,et al.  Establishment, characterization and determination of cell surface sugar receptor (lectin) expression by neoglycoenzymes of a human myeloid marker-expressing B lymphoblastoid cell line. , 1991, Anticancer research.

[72]  H. Gabius Influence of type of linkage and spacer on the interaction of beta-galactoside-binding proteins with immobilized affinity ligands. , 1990, Analytical biochemistry.

[73]  R. Lee,et al.  Binding characteristics of galactoside-binding lectin (galaptin) from human spleen. , 1990, The Journal of biological chemistry.

[74]  A. Pavia,et al.  Réduction-acetylation sélective des azido-sucres par le mélange acide thioacétique-thioacétate de potassium , 1990 .

[75]  H. Gabius Tumorlectinologie: Ein Gebiet im Schnittpunkt von Zuckerchemie, Biochemie, Zellbiologie und Onkologie† , 1988 .

[76]  Hans-Joachim Gabius,et al.  Tumor Lectinology: At the Intersection of Carbohydrate Chemistry, Biochemistry, Cell Biology, and Oncology , 1988 .

[77]  S. Barondes,et al.  Specificity of binding of three soluble rat lung lectins to substituted and unsubstituted mammalian beta-galactosides. , 1986, The Journal of biological chemistry.

[78]  Nathan Sharon,et al.  The Lectins: Properties, Functions and Applications in Biology and Medicine , 1986 .

[79]  R. Hill,et al.  The binding of fucose-containing glycoproteins by hepatic lectins. The binding specificity of the rat liver fucose lectin. , 1986, The Journal of biological chemistry.

[80]  H. Gabius,et al.  Biochemical characterization of endogenous carbohydrate-binding proteins from spontaneous murine rhabdomyosarcoma, mammary adenocarcinoma, and ovarian teratoma. , 1984, Journal of the National Cancer Institute.

[81]  S. Kornfeld,et al.  Isolation and properties of beta-galactoside binding lectins of calf heart and lung. , 1976, The Journal of biological chemistry.

[82]  N. Pravdic,et al.  An improved synthesis of the 2-acetamido-d-glucal derivative 3,4,6-tri-O-acetyl-2-(N-acetylacetamido)-1,5-anhydro-2-deoxy-d-arabino-hex-1-enitol , 1975 .

[83]  Hans-Joachim Gabius,et al.  Cell surface glycans: the why and how of their functionality as biochemical signals in lectin-mediated information transfer. , 2006, Critical reviews in immunology.

[84]  R. Schmidt,et al.  Synthetic routes to thiooligosaccharides and thioglycopeptides. , 2006, Chemical reviews.

[85]  Albert J R Heck,et al.  Carbohydrate chain of ganglioside GM1 as a ligand: identification of the binding strategies of three 15 mer peptides and their divergence from the binding modes of growth-regulatory galectin-1 and cholera toxin. , 2005, Chemistry.

[86]  H. Gabius,et al.  Lectin localization in human nerve by biochemically defined lectin-binding glycoproteins, neoglycoprotein and lectin-specific antibody , 2004, Histochemistry.

[87]  K. Kayser,et al.  Determination of modulation of ligand properties of synthetic complex-type biantennary N-glycans by introduction of bisecting GlcNAc in silico, in vitro and in vivo. , 2004, European journal of biochemistry.

[88]  Y. Takenaka,et al.  Galectin-3 and metastasis , 2004, Glycoconjugate Journal.

[89]  H. Gabius,et al.  Persubstituted cyclodextrin-based glycoclusters as inhibitors of protein-carbohydrate recognition using purified plant and mammalian lectins and wild-type and lectin-gene-transfected tumor cells as targets. , 2004, Bioconjugate chemistry.

[90]  H. Gabius,et al.  Describing topology of bound ligand by transferred nuclear Overhauser effect spectroscopy and molecular modeling. , 2003, Methods in enzymology.

[91]  I. Goldstein,et al.  [16] Carbohydrate antigens: Coupling of carbohydrates to proteins by diazonium and phenylisothiocyanate reactions , 1972 .