Thioglycuronides: synthesis and application in the assembly of acidic oligosaccharides.

PubWeight™: 1.11‹?› | Rank: Top 10%

🔗 View Article (PMID 15200311)

Published in Org Lett on June 24, 2004

Authors

Leendert J van den Bos1, Jeroen D C Codée, John C van der Toorn, Thomas J Boltje, Jacques H van Boom, Herman S Overkleeft, Gijsbert A van der Marel

Author Affiliations

1: Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.

Articles citing this

Modular synthesis of heparan sulfate oligosaccharides for structure-activity relationship studies. J Am Chem Soc (2009) 1.72

Preactivation-based, one-pot combinatorial synthesis of heparin-like hexasaccharides for the analysis of heparin-protein interactions. Chemistry (2010) 1.22

A facile method for oxidation of primary alcohols to carboxylic acids and its application in glycosaminoglycan syntheses. Chemistry (2006) 1.11

Installation of electron-donating protective groups, a strategy for glycosylating unreactive thioglycosyl acceptors using the preactivation-based glycosylation method. J Org Chem (2008) 1.00

IMPROVED SYNTHESIS OF 1-BENZENESULFINYL PIPERIDINE AND ANALOGS FOR THE ACTIVATION OF THIOGLYCOSIDES IN CONJUNCTION WITH TRIFLUOROMETHANESULFONIC ANHYDRIDE. J Carbohydr Chem (2005) 1.00

Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides. J Org Chem (2011) 0.90

Electrochemical generation of glycosyl triflate pools. J Am Chem Soc (2007) 0.90

Strategies in synthesis of heparin/heparan sulfate oligosaccharides: 2000-present. Adv Carbohydr Chem Biochem (2012) 0.88

Chemical synthesis of a heparan sulfate glycopeptide: syndecan-1. Angew Chem Int Ed Engl (2012) 0.83

Chemical synthesis of syndecan-3 glycopeptides bearing two heparan sulfate glycan chains. Angew Chem Int Ed Engl (2014) 0.79

Fluorous-assisted chemoenzymatic synthesis of heparan sulfate oligosaccharides. Org Lett (2014) 0.79

New glucuronic acid donors for the modular synthesis of heparan sulfate oligosaccharides. Org Biomol Chem (2014) 0.78

Divergent Synthesis of Heparan Sulfate Oligosaccharides. J Org Chem (2015) 0.77

Synthesis and reactivity of 4'-deoxypentenosyl disaccharides. J Org Chem (2014) 0.76

Design and synthesis of unnatural heparosan and chondroitin building blocks. J Org Chem (2011) 0.76

Homoserine as an Aspartic Acid Precursor for Synthesis of Proteoglycan Glycopeptide Containing Aspartic Acid and a Sulfated Glycan Chain. J Org Chem (2016) 0.75

Obstacles and solutions for chemical synthesis of syndecan-3 (53-62) glycopeptides with two heparan sulfate chains. Carbohydr Res (2016) 0.75

Articles by these authors

Asymmetric proteasome segregation as a mechanism for unequal partitioning of the transcription factor T-bet during T lymphocyte division. Immunity (2011) 2.34

Proteasome inhibitors: an expanding army attacking a unique target. Chem Biol (2012) 2.26

Analysis of protease activity in live antigen-presenting cells shows regulation of the phagosomal proteolytic contents during dendritic cell activation. J Exp Med (2002) 1.64

Thioglycosides in sequential glycosylation strategies. Chem Soc Rev (2005) 1.60

Microreactors as tools for synthetic chemists-the chemists' round-bottomed flask of the 21st century? Chemistry (2006) 1.56

A fluorescent broad-spectrum proteasome inhibitor for labeling proteasomes in vitro and in vivo. Chem Biol (2006) 1.54

Selective inhibitor of proteasome's caspase-like sites sensitizes cells to specific inhibition of chymotrypsin-like sites. Chem Biol (2009) 1.47

The caspase-like sites of proteasomes, their substrate specificity, new inhibitors and substrates, and allosteric interactions with the trypsin-like sites. J Biol Chem (2003) 1.46

Synthesis of pH-activatable red fluorescent BODIPY dyes with distinct functionalities. Org Lett (2011) 1.44

Ph2SO/Tf2O: a powerful promotor system in chemoselective glycosylations using thioglycosides. Org Lett (2003) 1.42

Glycosphingolipids--nature, function, and pharmacological modulation. Angew Chem Int Ed Engl (2009) 1.41

Biochemical and genetic studies of the VPg uridylylation reaction catalyzed by the RNA polymerase of poliovirus. J Virol (2003) 1.37

Development of adamantan-1-yl-methoxy-functionalized 1-deoxynojirimycin derivatives as selective inhibitors of glucosylceramide metabolism in man. J Org Chem (2007) 1.28

Muscle wasting in aged, sarcopenic rats is associated with enhanced activity of the ubiquitin proteasome pathway. J Biol Chem (2010) 1.28

Ultrasensitive in situ visualization of active glucocerebrosidase molecules. Nat Chem Biol (2010) 1.26

Chemistry in living cells: detection of active proteasomes by a two-step labeling strategy. Angew Chem Int Ed Engl (2003) 1.25

Distinct uptake mechanisms but similar intracellular processing of two different toll-like receptor ligand-peptide conjugates in dendritic cells. J Biol Chem (2007) 1.23

Crystal structure of HslUV complexed with a vinyl sulfone inhibitor: corroboration of a proposed mechanism of allosteric activation of HslV by HslU. J Mol Biol (2002) 1.21

Metal-free sequential [3 + 2]-dipolar cycloadditions using cyclooctynes and 1,3-dipoles of different reactivity. J Am Chem Soc (2010) 1.19

A modular strategy toward the synthesis of heparin-like oligosaccharides using monomeric building blocks in a sequential glycosylation strategy. J Am Chem Soc (2005) 1.17

Transglycosidase activity of chitotriosidase: improved enzymatic assay for the human macrophage chitinase. J Biol Chem (2003) 1.16

Recognition of base J in duplex DNA by J-binding protein. J Biol Chem (2001) 1.15

The conformation of neurotensin bound to its G protein-coupled receptor. Proc Natl Acad Sci U S A (2003) 1.14

Structure and reactivity of an asymmetric complex between HslV and I-domain deleted HslU, a prokaryotic homolog of the eukaryotic proteasome. J Mol Biol (2003) 1.13

Specific cell-permeable inhibitor of proteasome trypsin-like sites selectively sensitizes myeloma cells to bortezomib and carfilzomib. Chem Biol (2011) 1.13

Oligosaccharide synthesis in microreactors. Org Lett (2007) 1.10

Bioorthogonal organic chemistry in living cells: novel strategies for labeling biomolecules. Org Biomol Chem (2004) 1.08

Biomarkers in the diagnosis of lysosomal storage disorders: proteins, lipids, and inhibodies. J Inherit Metab Dis (2011) 1.07

Mixing of peptides and electrophilic traps gives rise to potent, broad-spectrum proteasome inhibitors. Org Biomol Chem (2007) 1.07

Small-molecule inhibitors and probes for ubiquitin- and ubiquitin-like-specific proteases. Chembiochem (2005) 1.07

The use of cyclic bifunctional protecting groups in oligosaccharide synthesis--an overview. Carbohydr Res (2006) 1.04

Automated solid-phase synthesis of β-mannuronic acid alginates. Angew Chem Int Ed Engl (2012) 1.02

Activity-based profiling reveals reactivity of the murine thymoproteasome-specific subunit beta5t. Chem Biol (2010) 1.01

Targeting aberrant sialylation in cancer cells using a fluorinated sialic acid analog impairs adhesion, migration, and in vivo tumor growth. Mol Cancer Ther (2013) 1.01

Development of an activity-based probe and in silico design reveal highly selective inhibitors for diacylglycerol lipase-α in brain. Angew Chem Int Ed Engl (2013) 1.01

Functional proteomics of the active cysteine protease content in Drosophila S2 cells. Mol Cell Proteomics (2003) 1.01

Quantification of globotriaosylsphingosine in plasma and urine of fabry patients by stable isotope ultraperformance liquid chromatography-tandem mass spectrometry. Clin Chem (2012) 0.98

Stereodirecting effect of the pyranosyl C-5 substituent in glycosylation reactions. J Org Chem (2009) 0.97

Syringolin A selectively labels the 20 S proteasome in murine EL4 and wild-type and bortezomib-adapted leukaemic cell lines. Chembiochem (2009) 0.97

The impact of oxacarbenium ion conformers on the stereochemical outcome of glycosylations. Carbohydr Res (2010) 0.96

A cell-permeable inhibitor and activity-based probe for the caspase-like activity of the proteasome. Bioorg Med Chem Lett (2007) 0.96

Relative quantification of proteasome activity by activity-based protein profiling and LC-MS/MS. Nat Protoc (2013) 0.96

Sequential one-pot glycosylations using 1-hydroxyl and 1-thiodonors. Org Lett (2003) 0.94

Nature of pharmacophore influences active site specificity of proteasome inhibitors. J Biol Chem (2010) 0.94

Human B lymphoblastoid cells contain distinct patterns of cathepsin activity in endocytic compartments and regulate MHC class II transport in a cathepsin S-independent manner. J Leukoc Biol (2004) 0.94

Acetylene functionalized BODIPY dyes and their application in the synthesis of activity based proteasome probes. Bioorg Med Chem Lett (2007) 0.94

Conjugation of nucleosides and oligonucleotides by [3+2] cycloaddition. J Org Chem (2007) 0.93

Automated solid-phase synthesis of hyaluronan oligosaccharides. Org Lett (2012) 0.93

Incorporation of non-natural amino acids improves cell permeability and potency of specific inhibitors of proteasome trypsin-like sites. J Med Chem (2013) 0.92

Novel activity-based probes for broad-spectrum profiling of retaining β-exoglucosidases in situ and in vivo. Angew Chem Int Ed Engl (2012) 0.92

Minitags for small molecules: detecting targets of reactive small molecules in living plant tissues using 'click chemistry'. Plant J (2008) 0.91

Bioorthogonal chemistry: applications in activity-based protein profiling. Acc Chem Res (2011) 0.91

Activity-based protein profiling: an enabling technology in chemical biology research. Curr Opin Chem Biol (2012) 0.91

Synthesis of hyaluronic acid oligomers using Ph2SO/Tf2O-mediated glycosylations. J Org Chem (2007) 0.90

Assessing subunit dependency of the Plasmodium proteasome using small molecule inhibitors and active site probes. ACS Chem Biol (2014) 0.90

Azido-BODIPY acid reveals quantitative Staudinger-Bertozzi ligation in two-step activity-based proteasome profiling. Chembiochem (2008) 0.90

Equatorial anomeric triflates from mannuronic acid esters. J Am Chem Soc (2009) 0.90

Structural and biological evaluation of some loloatin C analogues. Bioorg Med Chem (2009) 0.90

Synthesis and evaluation of homo-bivalent GnRHR ligands. Bioorg Med Chem (2007) 0.90

The C-terminal region of Escherichia coli UvrC contributes to the flexibility of the UvrABC nucleotide excision repair system. Nucleic Acids Res (2002) 0.89

Mannosazide methyl uronate donors. Glycosylating properties and use in the construction of β-ManNAcA-containing oligosaccharides. J Org Chem (2010) 0.89

A panel of subunit-selective activity-based proteasome probes. Org Biomol Chem (2010) 0.89

2-Azidoalkoxy-7-hydro-8-oxoadenine derivatives as TLR7 agonists inducing dendritic cell maturation. Bioorg Med Chem Lett (2009) 0.89

Uronic acids in oligosaccharide and glycoconjugate synthesis. Top Curr Chem (2011) 0.89