Regioselective one-pot protection of carbohydrates.

PubWeight™: 1.87‹?› | Rank: Top 3%

🔗 View Article (PMID 17443183)

Published in Nature on April 19, 2007

Authors

Cheng-Chung Wang1, Jinq-Chyi Lee, Shun-Yuan Luo, Suvarn S Kulkarni, Yu-Wen Huang, Chia-Chen Lee, Ken-Lien Chang, Shang-Cheng Hung

Author Affiliations

1: Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan.

Articles citing this

Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research. Nat Chem (2009) 2.09

Site-selective catalysis of phenyl thionoformate transfer as a tool for regioselective deoxygenation of polyols. J Org Chem (2008) 1.19

Immunotherapy for cancer: synthetic carbohydrate-based vaccines. Chem Commun (Camb) (2009) 1.14

Synthetically defined glycoprotein vaccines: current status and future directions. Chem Sci (2013) 0.97

Recent progress in chemical and chemoenzymatic synthesis of carbohydrates. Curr Opin Chem Biol (2009) 0.96

Versatile set of orthogonal protecting groups for the preparation of highly branched oligosaccharides. Org Lett (2010) 0.96

Chemoenzymatic elaboration of monosaccharides using engineered cytochrome P450BM3 demethylases. Proc Natl Acad Sci U S A (2009) 0.96

Chiral-auxiliary-mediated 1,2-cis-glycosylations for the solid-supported synthesis of a biologically important branched alpha-glucan. Nat Chem (2010) 0.91

Selective acetylation of per-O-TMS-protected monosaccharides. Org Lett (2010) 0.90

De novo asymmetric synthesis of all-D-, all-L-, and D-/L-oligosaccharides using atom-less protecting groups. J Am Chem Soc (2012) 0.86

Regioselective silyl/acetate exchange of disaccharides yields advanced glycosyl donor and acceptor precursors. J Org Chem (2013) 0.86

Superarmed and superdisarmed building blocks in expeditious oligosaccharide synthesis. Top Curr Chem (2011) 0.86

Oligomannan synthesis using ionic liquid supported glycosylation. Org Lett (2007) 0.86

Glycobiology: A spoonful of sugar. Nature (2009) 0.85

Direct synthesis of diastereomerically pure glycosyl sulfonium salts. Org Lett (2011) 0.85

Realizing the Promise of Chemical Glycobiology. Chem Sci (2013) 0.82

Integrating ReSET with glycosyl iodide glycosylation in step-economy syntheses of tumor-associated carbohydrate antigens and immunogenic glycolipids. J Org Chem (2014) 0.82

Mild Method for 2-Naphthylmethyl Ether Protecting Group Removal Using a Combination of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and β-Pinene. J Org Chem (2017) 0.81

4-(pyridin-2-yl)thiazol-2-yl thioglycosides as bidentate ligands for oligosaccharide synthesis via temporary deactivation. Chem Commun (Camb) (2008) 0.79

One-pot synthesis of oligosaccharides by combining reductive openings of benzylidene acetals and glycosylations. Org Lett (2008) 0.79

Regioselective Benzylation of 2-Deoxy-2-Aminosugars Using Crown Ethers: Application to a Shortened Synthesis of Hyaluronic Acid Oligomers. Adv Synth Catal (2014) 0.78

Superarming of glycosyl donors by combined neighboring and conformational effects. Org Lett (2013) 0.78

Regioselective monodeprotection of peracetylated carbohydrates. Nat Protoc (2012) 0.76

Synthesis of orthogonally protected bacterial, rare-sugar and D-glycosamine building blocks. Nat Protoc (2013) 0.76

Total synthesis of tetraacylated phosphatidylinositol hexamannoside and evaluation of its immunomodulatory activity. Nat Commun (2015) 0.76

2-Acetyl-amino-1,3,4,6-tetra-O-(tri-methyl-silyl)-2-de-oxy-α-d-gluco-pyran-ose. Acta Crystallogr Sect E Struct Rep Online (2013) 0.75

Orthogonal protection of saccharide polyols through solvent-free one-pot sequences based on regioselective silylations. Beilstein J Org Chem (2016) 0.75

Total synthesis of mycobacterial arabinogalactan containing 92 monosaccharide units. Nat Commun (2017) 0.75

Synthesis of the carboline disaccharide domain of shishijimicin A. Org Lett (2011) 0.75

Glycosyl Thioimidates as Versatile Building Blocks for Organic Synthesis. Chem Heterocycl Compd (N Y) (2012) 0.75

Articles by these authors

Synthesis of heparin oligosaccharides. J Am Chem Soc (2004) 1.41

Efficient, one-pot syntheses of biologically active alpha-linked glycolipids. Chem Commun (Camb) (2007) 1.34

A nanostructure-initiator mass spectrometry-based enzyme activity assay. Proc Natl Acad Sci U S A (2008) 1.27

Synthesis of 3-O-sulfonated heparan sulfate octasaccharides that inhibit the herpes simplex virus type 1 host-cell interaction. Nat Chem (2011) 1.25

Toward automated oligosaccharide synthesis. Angew Chem Int Ed Engl (2011) 1.20

Design of a robust infrastructure to monitor the safety of the pandemic A(H1N1) 2009 vaccination program in Taiwan. Vaccine (2010) 1.18

One-pot syntheses of immunostimulatory glycolipids. J Org Chem (2010) 1.13

Structural analysis of the extracellular domain of vaccinia virus envelope protein, A27L, by NMR and CD spectroscopy. J Biol Chem (2002) 1.13

Hepatitis C virus NS3 RNA helicase activity is modulated by the two domains of NS3 and NS4A. Biochem Biophys Res Commun (2004) 1.02

Synthesis of 48 disaccharide building blocks for the assembly of a heparin and heparan sulfate oligosaccharide library. Org Lett (2006) 0.99

Facile Cu(OTf)2-catalyzed preparation of per-O-acetylated hexopyranoses with stoichiometric acetic anhydride and sequential one-pot anomeric substitution to thioglycosides under solvent-free conditions. J Org Chem (2003) 0.93

Repeated light-dark shifts speed up body weight gain in male F344 rats. Am J Physiol Endocrinol Metab (2005) 0.92

Usage of the claim database of national health insurance programme for analysis of cisapride-erythromycin co-medication in Taiwan. Pharmacoepidemiol Drug Saf (2007) 0.90

Regioselective one-pot protection of glucose. Nat Protoc (2008) 0.90

2-Allylphenyl glycosides as glycosyl donors for sugar coupling. Carbohydr Res (2012) 0.89

Synthesis of biologically potent alpha1-->2-linked disaccharide derivatives via regioselective one-pot protection-glycosylation. Angew Chem Int Ed Engl (2002) 0.89

A concise synthesis of tetrahydroxy-LCB, alpha-galactosyl ceramide, and 1,4-dideoxy-1,4-imino-L-ribitol via D-allosamines as key building blocks. J Org Chem (2006) 0.89

Divergent synthesis of 48 heparan sulfate-based disaccharides and probing the specific sugar-fibroblast growth factor-1 interaction. J Am Chem Soc (2012) 0.88

α-Glycosylation by D-glucosamine-derived donors: synthesis of heparosan and heparin analogues that interact with mycobacterial heparin-binding hemagglutinin. J Am Chem Soc (2012) 0.87

Aclacinomycin A sensitizes K562 chronic myeloid leukemia cells to imatinib through p38MAPK-mediated erythroid differentiation. PLoS One (2013) 0.87

Cu(OTf)2 as an efficient and dual-purpose catalyst in the regioselective reductive ring opening of benzylidene acetals. Angew Chem Int Ed Engl (2005) 0.87

Selective inhibition of the NLRP3 inflammasome by targeting to promyelocytic leukemia protein in mouse and human. Blood (2013) 0.86

Adverse events following pandemic A (H1N1) 2009 monovalent vaccines in pregnant women--Taiwan, November 2009-August 2010. PLoS One (2011) 0.86

The reporting completeness of a passive safety surveillance system for pandemic (H1N1) 2009 vaccines: a capture-recapture analysis. Vaccine (2012) 0.86

SOX2 modulates alternative splicing in transitional cell carcinoma. Biochem Biophys Res Commun (2010) 0.85

Synthetic heparin and heparan sulfate oligosaccharides and their protein interactions. Curr Opin Chem Biol (2013) 0.85

Acyl and silyl group effects in reactivity-based one-pot glycosylation: synthesis of embryonic stem cell surface carbohydrates Lc4 and IV(2)Fuc-Lc4. J Am Chem Soc (2012) 0.85

Dynamic cerebral autoregulation in carotid stenosis before and after carotid stenting. J Vasc Surg (2008) 0.84

The roles of ubiquitin and 26S proteasome in human obesity. Metabolism (2009) 0.84

Synthesis and biological evaluation of novel C-indolylxylosides as sodium-dependent glucose co-transporter 2 inhibitors. Eur J Med Chem (2012) 0.83

Anaplastic carcinoma of the thyroid arising more often from follicular carcinoma than papillary carcinoma. Ann Surg Oncol (2007) 0.83

Synthesis of heparin oligosaccharides and their interaction with eosinophil-derived neurotoxin. Org Biomol Chem (2011) 0.82

Compound heterozygous mutations in PYCR1 further expand the phenotypic spectrum of De Barsy syndrome. Am J Med Genet A (2011) 0.82

On the relationship between the sequence conservation and the packing density profiles of the protein complexes. Proteins (2013) 0.82

A novel mutation in PYCR1 causes an autosomal recessive cutis laxa with premature aging features in a family. Am J Med Genet A (2011) 0.81

One-pot strategies for the synthesis of the tetrasaccharide linkage region of proteoglycans. Org Lett (2011) 0.81

Neighboring group participation of 9-anthracenylmethyl group in glycosylation: preparation of unusual C-glycosides. J Org Chem (2005) 0.81

Ice plant (Mesembryanthemum crystallinum) improves hyperglycaemia and memory impairments in a Wistar rat model of streptozotocin-induced diabetes. J Sci Food Agric (2014) 0.81

A high-throughput cell-based screening for L858R/T790M mutant epidermal growth factor receptor inhibitors. Anticancer Res (2012) 0.81

Metal trifluoromethanesulfonate-catalyzed regioselective borane-reductive ring opening of benzylidene acetals: a concise synthesis of 1,4-dideoxy-1,4-imino-L-xylitol. Org Lett (2002) 0.81

Synthesis of the heparin-based anticoagulant drug fondaparinux. Angew Chem Int Ed Engl (2014) 0.81

Discovery of novel N-β-D-xylosylindole derivatives as sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the management of hyperglycemia in diabetes. J Med Chem (2010) 0.81

13C solid-state NMR chemical shift anisotropy analysis of the anomeric carbon in carbohydrates. Carbohydr Res (2005) 0.81

Synthesis of mycobacterial triacylated phosphatidylinositol dimannoside containing an acyl lipid chain at 3-O of inositol. Org Lett (2010) 0.81

Expeditious synthesis of bacterial, rare sugar building blocks to access the prokaryotic glycome. Org Biomol Chem (2013) 0.80

Regioselective one-pot protection of D-glucosamine. J Org Chem (2010) 0.80

One-pot synthesis of N-acetyl- and N-glycolylneuraminic acid capped trisaccharides and evaluation of their influenza A(H1 N1) inhibition. Angew Chem Int Ed Engl (2014) 0.80

Synthesis of a C-glycoside analogue of β-galactosyl ceramide, a potential HIV-1 entry inhibitor. J Org Chem (2013) 0.80

Synthesis of β-C-galactosyl D- and L-alanines. Org Biomol Chem (2012) 0.80

Rapid transformation of D-mannose into orthogonally protected D-glucosamine and D-galactosamine thioglycosides. J Org Chem (2011) 0.80

Regioselective and stereoselective benzylidene installation and one-pot protection of D-mannose. Org Biomol Chem (2013) 0.79

Is atypical follicular adenoma of the thyroid a preinvasive malignancy? Hum Pathol (2003) 0.79

Total synthesis of phosphatidylinositol dimannoside: a cell-envelope component of Mycobacterium tuberculosis. Chemistry (2009) 0.79

Effects of endogenous histamine on seizure development of pentylenetetrazole-induced kindling in rats. Pharmacology (2003) 0.79

Development of sodium-dependent glucose co-transporter 2 inhibitors as potential anti-diabetic therapeutics. Curr Top Med Chem (2011) 0.79

Cloning of murine early quiescence-1 gene: the murine counterpart of dermatopontin gene can induce and be induced by cell quiescence. Exp Cell Res (2004) 0.78

Arecoline induces TNF-alpha production and Zonula Occludens-1 redistribution in mouse Sertoli TM4 cells. J Biomed Sci (2014) 0.78

Photoinduced atom-transfer cyclization of alpha-iodocycloalkanones bearing an allenyl side chain. Org Lett (2004) 0.78

Discovery of non-glycoside sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors by ligand-based virtual screening. J Med Chem (2010) 0.78

Recent advances in synthesis of bacterial rare sugar building blocks and their applications. Nat Prod Rep (2014) 0.78

A cell-based high-throughput screen for epidermal growth factor receptor pathway inhibitors. Anal Biochem (2008) 0.78

The first total synthesis of cytopiloyne, an anti-diabetic, polyacetylenic glucoside. Chemistry (2011) 0.78

Low-frequency enzyme replacement therapy in late-onset Pompe disease. Muscle Nerve (2013) 0.78

Interactions that influence the binding of synthetic heparan sulfate based disaccharides to fibroblast growth factor-2. ACS Chem Biol (2014) 0.77

3-[2-((2S)-2-cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-3-methyl-butyramide analogues as selective DPP-IV inhibitors for the treatment of type-II diabetes. Bioorg Med Chem Lett (2006) 0.77

Rational design and synthesis of potent and long-lasting glutamic acid-based dipeptidyl peptidase IV inhibitors. Bioorg Med Chem Lett (2009) 0.77

Synthesis of maradolipid. J Org Chem (2011) 0.77

Immunohistochemical expression of Wilms' tumor 1 protein in nephroblastoma. J Chin Med Assoc (2004) 0.77

Orthogonally protected D-galactosamine thioglycoside building blocks via highly regioselective, double serial and double parallel inversions of β-D-thiomannoside. Org Biomol Chem (2013) 0.77

Generation of a monoclonal antibody specifically reacting with undifferentiated liver progenitor cells. Hybridoma (Larchmt) (2009) 0.77

Synthesis of L-hexoses and their related biomolecules. Chem Commun (Camb) (2013) 0.77

Quantitative analysis of plasma HBV DNA for early evaluation of the response to transcatheter arterial embolization for HBV-related hepatocellular carcinoma. World J Gastroenterol (2005) 0.76

Graptopetalum paraguayense and resveratrol ameliorates carboxymethyllysine (CML)-induced pancreas dysfunction and hyperglycemia. Food Chem Toxicol (2013) 0.76

Detection of porcine circovirus type 1 in commercial porcine vaccines by loop-mediated isothermal amplification. Folia Microbiol (Praha) (2011) 0.76

Regioselective one-pot protection, protection-glycosylation and protection-glycosylation-glycosylation of carbohydrates: a case study with D-glucose. Org Biomol Chem (2014) 0.76

Regioselective glycosylation of neamine core: a facile entry to kanamycin B related analogues. Org Lett (2004) 0.76

Regioselective one-pot protection and protection-glycosylation of carbohydrates. Chimia (Aarau) (2011) 0.76

Desymmetrization of 2,4,5,6-tetra-O-benzyl-D-myo-inositol for the synthesis of mycothiol. Org Lett (2011) 0.76

Synthesis of orthogonally protected bacterial, rare-sugar and D-glycosamine building blocks. Nat Protoc (2013) 0.76

Liquid crystal modified photonic crystal fiber (LC-PCF) fabricated with an un-cured SU-8 photoresist sealing technique for electrical flux measurement. Opt Express (2011) 0.75

Carbohydrate-templated asymmetric Diels-Alder reactions of masked ortho-benzoquinones for the synthesis of chiral bicyclo[2.2.2]oct-5-en-2-ones. Angew Chem Int Ed Engl (2008) 0.75

First synthesis of Bacillus cereus Ch HF-PS cell wall trisaccharide repeating unit. Org Lett (2014) 0.75

Expeditious synthesis of Mycobacterium tuberculosis sulfolipids SL-1 and Ac2SGL analogues. Org Lett (2014) 0.75