Carbohydrate chemistry in drug discovery

Self-Adjuvanting Multicomponent Cancer Vaccine Candidates Combining Per-Glycosylated MUC1 Glycopeptides and the Toll-like Receptor 2 Agonist Pam3CysSer

(2011) Brendan L. Wilkinson et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Iron(iii) chloride-tandem catalysis for a one-pot regioselective protection of glycopyranosides

(2011) Yann Bourdreux et al.   CHEMICAL COMMUNICATIONS

Synthetic Antitumor Vaccines from Tetanus Toxoid Conjugates of MUC1 Glycopeptides with the Thomsen-Friedenreich Antigen and a Fluorine-Substituted Analogue

(2010) Anja Hoffmann-Röder et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Synthesis and Immunogenicity of a Glycopolymer Conjugate

(2010) Tomasz Lipinski et al.   BIOCONJUGATE CHEMISTRY

Iodine-catalyzed one-pot acetalation–esterification reaction for the preparation of orthogonally protected glycosides

(2010) Rachel A. Jones et al.   CARBOHYDRATE RESEARCH

Synthesis of MUC1–lipopeptide chimeras

(2010) Brendan L. Wilkinson et al.   CHEMICAL COMMUNICATIONS

Defining Criteria for Oligomannose Immunogens for HIV Using Icosahedral Virus Capsid Scaffolds

(2010) Rena D. Astronomo et al.   CHEMISTRY & BIOLOGY

Preactivation-Based, One-Pot Combinatorial Synthesis of Heparin-like Hexasaccharides for the Analysis of Heparin-Protein Interactions

(2010) Zhen Wang et al.   CHEMISTRY-A EUROPEAN JOURNAL

Recent Trends in Regioselective Protection and Deprotection of Monosaccharides

(2010) Marco Filice et al.   CURRENT ORGANIC CHEMISTRY

Fluorous-Assisted One-Pot Oligosaccharide Synthesis

(2010) Bo Yang et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Preparation, characterization and immunogenicity of HIV-1 related high-mannose oligosaccharides-CRM197 glycoconjugates

(2010) Anna Kabanova et al.   GLYCOCONJUGATE JOURNAL

Synthesis and Biological Evaluation of Polysulfated Oligosaccharide Glycosides as Inhibitors of Angiogenesis and Tumor Growth

(2010) Ken D. Johnstone et al.   JOURNAL OF MEDICINAL CHEMISTRY

Regioselective One-Pot Protection ofd-Glucosamine

(2010) Ken-Lien Chang et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthesis of a Single-Moleculel-Rhamnose-Containing Three-Component Vaccine and Evaluation of Antigenicity in the Presence of Anti-l-Rhamnose Antibodies

(2010) Sourav Sarkar et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A shift for the O-GlcNAc paradigm

(2010) Jennifer J Kohler   Nature Chemical Biology

Quantification of O-glycosylation stoichiometry and dynamics using resolvable mass tags

(2010) Jessica E Rexach et al.   Nature Chemical Biology

Glycopeptide-specific monoclonal antibodies suggest new roles for O-GlcNAc

(2010) Chin Fen Teo et al.   Nature Chemical Biology

Chiral-auxiliary-mediated 1,2-cis-glycosylations for the solid-supported synthesis of a biologically important branched α-glucan

(2010) Thomas J. Boltje et al.   Nature Chemistry

Carbohydrate vaccines: developing sweet solutions to sticky situations?

(2010) Rena D. Astronomo et al.   NATURE REVIEWS DRUG DISCOVERY

Exploring neoglycoprotein assembly through native chemical ligation using neoglycopeptide thioesters prepared via N→S acyl transfer

(2010) Jonathan P. Richardson et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Access to phosphoproteins and glycoproteins through semi-synthesis, Native Chemical Ligation and N→S acyl transfer

(2010) Jinit Masania et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Linear and Branched Glyco-Lipopeptide Vaccines Follow Distinct Cross-Presentation Pathways and Generate Different Magnitudes of Antitumor Immunity

(2010) Olivier Renaudet et al.   PLoS One

Antibody recognition of a unique tumor-specific glycopeptide antigen

(2010) C. L. Brooks et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

A nonself sugar mimic of the HIV glycan shield shows enhanced antigenicity

(2010) K. J. Doores et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Synthesis of 2-aminoethyl 3′-(N-glycolylneuraminyl)-β-actoside and neoglycoconjugates based thereon — a prototype of a cancer vaccine and artificial antigens for the control of immune response

(2010) E. A. Khatuntseva et al.   RUSSIAN CHEMICAL BULLETIN

Synthesis of N-modified sTn analogs and evaluation of their immunogenicities by microarray-based immunoassay

(2010) Sk Sahabuddin et al.   TETRAHEDRON

Semisynthesis of a Homogeneous Glycoprotein Enzyme: Ribonuclease C: Part 1

(2009) Christian Piontek et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Semisynthesis of a Homogeneous Glycoprotein Enzyme: Ribonuclease C: Part 2

(2009) Christian Piontek et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Design and Synthesis of a Homogeneous Erythropoietin Analogue with Two Human Complex-Type Sialyloligosaccharides: Combined Use of Chemical and Bacterial Protein Expression Methods

(2009) Kiriko Hirano et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

A Synthetic Vaccine Consisting of a Tumor-Associated Sialyl-TN-MUC1 Tandem-Repeat Glycopeptide and Tetanus Toxoid: Induction of a Strong and Highly Selective Immune Response

(2009) Anton Kaiser et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

New Principles for Glycoside-Bond Formation

(2009) Xiangming Zhu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Synthesis of sialyl Lewisa (sLea, CA19-9) and construction of an immunogenic sLea vaccine

(2009) Govind Ragupathi et al.   CANCER IMMUNOLOGY IMMUNOTHERAPY

Enhanced Immune Recognition of Cryptic Glycan Markers in Human Tumors

(2009) T. E. Newsom-Davis et al.   CANCER RESEARCH

Efficient synthesis and protein conjugation of β-(1→6)-d-N-acetylglucosamine oligosaccharides from the polysaccharide intercellular adhesin

(2009) Carmen Leung et al.   CARBOHYDRATE RESEARCH

Increasing the Antigenicity of Synthetic Tumor-Associated Carbohydrate Antigens by Targeting Toll-Like Receptors

(2009) Sampat Ingale et al.   CHEMBIOCHEM

STICS: surface-tethered iterative carbohydrate synthesis

(2009) Papapida Pornsuriyasak et al.   CHEMICAL COMMUNICATIONS

Induction of a Melanoma-Specific Antibody Response by a Monovalent, but not a Divalent, Synthetic GM2 Neoglycopeptide

(2009) S. Bay et al.   ChemMedChem

Multimeric bivalent immunogens from recombinant tetanus toxin HC fragment, synthetic hexasaccharides, and a glycopeptide adjuvant

(2009) Aileen F. G. Bongat et al.   GLYCOCONJUGATE JOURNAL

Heparin: an intervenor in cell communication

(2009) Xianxiang Xu et al.   JOURNAL OF CELLULAR AND MOLECULAR MEDICINE

A Synthetic Carbohydrate-Protein Conjugate Vaccine Candidate against Shigella flexneri 2a Infection

(2009) A. Phalipon et al.   JOURNAL OF IMMUNOLOGY

A Practical Total Synthesis of Globo-H for Use in Anticancer Vaccines

(2009) Insik Jeon et al.   JOURNAL OF ORGANIC CHEMISTRY

On the Emerging Role of Chemistry in the Fashioning of Biologics: Synthesis of a Bidomainal Fucosyl GM1-Based Vaccine for the Treatment of Small Cell Lung Cancer

(2009) Pavel Nagorny et al.   JOURNAL OF ORGANIC CHEMISTRY

Synthesis and Applications of a Light-Fluorous Glycosyl Donor

(2009) Fa Zhang et al.   JOURNAL OF ORGANIC CHEMISTRY

Imidazolium Cation Supported Solution-Phase Assembly of Homolinear α(1→6)−Linked Octamannoside: An Efficient Alternate Approach for Oligosaccharide Synthesis

(2009) Charu K. Yerneni et al.   JOURNAL OF ORGANIC CHEMISTRY

From Synthesis to Biologics: Preclinical Data on a Chemistry Derived Anticancer Vaccine

(2009) Jianglong Zhu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Modular Synthesis of Heparan Sulfate Oligosaccharides for Structure−Activity Relationship Studies

(2009) Sailaja Arungundram et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A Convenient Catalyst for Aqueous and Protein Suzuki−Miyaura Cross-Coupling

(2009) Justin M. Chalker et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enrichment and Site Mapping ofO-LinkedN-Acetylglucosamine by a Combination of Chemical/Enzymatic Tagging, Photochemical Cleavage, and Electron Transfer Dissociation Mass Spectrometry

(2009) Zihao Wang et al.   MOLECULAR & CELLULAR PROTEOMICS

The repertoire of glycan determinants in the human glycome

(2009) Richard D. Cummings   Molecular BioSystems

Design of biologically active heparan sulfate and heparin using an enzyme-based approach

(2009) Sherket Peterson et al.   NATURAL PRODUCT REPORTS

Lessons learned from the contamination of heparin

(2009) Haiying Liu et al.   NATURAL PRODUCT REPORTS

A synthetic CD4–heparan sulfate glycoconjugate inhibits CCR5 and CXCR4 HIV-1 attachment and entry

(2009) Françoise Baleux et al.   Nature Chemical Biology

Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research

(2009) Thomas J. Boltje et al.   Nature Chemistry

From carbohydrate leads to glycomimetic drugs

(2009) Beat Ernst et al.   NATURE REVIEWS DRUG DISCOVERY

Sugars and proteins: New strategies in synthetic biology

(2009) Benjamin G. Davis   PURE AND APPLIED CHEMISTRY

‘Biologic’ level structures through chemistry: a total synthesis of a unimolecular pentavalent MUCI glycopeptide construct

(2009) Dongjoo Lee et al.   TETRAHEDRON LETTERS

Synthesis of phosphorylated Neisseria meningitidis inner core lipopolysaccharide structures

(2009) Johan D.M. Olsson et al.   TETRAHEDRON-ASYMMETRY

Increased immunogenicity of HIV-1 p24 and gp120 following immunization with gp120/p24 fusion protein vaccine expressing α-gal epitopes

(2009) Ussama M. Abdel-Motal et al.   VACCINE

Identification of new O-GlcNAc modified proteins using a click-chemistry-based tagging

(2008) Caroline Gurcel et al.   ANALYTICAL AND BIOANALYTICAL CHEMISTRY

Synthetic and Immunological Studies of5′-N-Phenylacetyl sTn to Develop Carbohydrate-Based Cancer Vaccines and to Explore the Impacts of Linkage between Carbohydrate Antigens and Carrier Proteins

(2008) Qianli Wang et al.   BIOCONJUGATE CHEMISTRY

Calix[4]arene Decorated with Four Tn Antigen Glycomimetic Units and P3CS Immunoadjuvant: Synthesis, Characterization, and Anticancer Immunological Evaluation

(2008) Corrada Geraci et al.   BIOCONJUGATE CHEMISTRY

Synthesis of a Streptococcus pyogenes vaccine candidate based on the M protein PL1 epitope

(2008) Pavla Simerska et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Antitumor activity of a self-adjuvanting glyco-lipopeptide vaccine bearing B cell, CD4+ and CD8+ T cell epitopes

(2008) Ilham Bettahi et al.   CANCER IMMUNOLOGY IMMUNOTHERAPY

The Structure of Glycosaminoglycans and their Interactions with Proteins

(2008) Neha S. Gandhi et al.   Chemical Biology & Drug Design

Glycoprotein Synthesis: An Update

(2008) David P. Gamblin et al.   CHEMICAL REVIEWS

A Novel Linker Methodology for the Synthesis of Tailored Conjugate Vaccines Composed of Complex Carbohydrate Antigens and Specific TH‐Cell Peptide Epitopes

(2008) Sebastian Dziadek et al.   CHEMISTRY-A EUROPEAN JOURNAL

Automated Solid-Phase Synthesis of Protected Oligosaccharides Containing β-Mannosidic Linkages

(2008) Jeroen D. C. Codée et al.   CHEMISTRY-A EUROPEAN JOURNAL

Cowpea Mosaic Virus Capsid: A Promising Carrier for the Development of Carbohydrate Based Antitumor Vaccines

(2008) Adeline Miermont et al.   CHEMISTRY-A EUROPEAN JOURNAL

Towards a Self-Adjuvanting Multivalent B and T cell Epitope Containing Synthetic Glycolipopeptide Cancer Vaccine

(2008) Olivier Renaudet et al.   ChemMedChem

Recent Developments in Synthetic Oligosaccharide-Based Bacterial Vaccines

(2008) Vince Pozsgay   CURRENT TOPICS IN MEDICINAL CHEMISTRY

Identification of the Smallest Structure Capable of Evoking Opsonophagocytic Antibodies against Streptococcus pneumoniae Type 14

(2008) D. Safari et al.   INFECTION AND IMMUNITY

Allyl Sulfides Are Privileged Substrates in Aqueous Cross-Metathesis: Application to Site-Selective Protein Modification

(2008) Yuya A. Lin et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Neuroactive Chondroitin Sulfate Glycomimetics

(2008) Manish Rawat et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Solution Structures of Chemoenzymatically Synthesized Heparin and Its Precursors

(2008) Zhenqing Zhang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Sugar-Assisted Glycopeptide Ligation with Complex Oligosaccharides: Scope and Limitations

(2008) Clay S. Bennett et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Direct In-Gel Fluorescence Detection and Cellular Imaging ofO-GlcNAc-Modified Proteins

(2008) Peter M. Clark et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

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

(2008) R. D. Astronomo et al.   JOURNAL OF VIROLOGY

Protein-glycan interactions in the control of innate and adaptive immune responses

(2008) Yvette van Kooyk et al.   NATURE IMMUNOLOGY

Toward solution-phase automated iterative synthesis: fluorous-tag assisted solution-phase synthesis of linear and branched mannose oligomers

(2008) Firoz A. Jaipuri et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Synthesis of Fluorous Tags for Incorporation of Reducing Sugars into a Quantitative Microarray Platform

(2008) Guo-Song Chen et al.   ORGANIC LETTERS

An oligosaccharide-based HIV-1 2G12 mimotope vaccine induces carbohydrate-specific antibodies that fail to neutralize HIV-1 virions

(2008) J. G. Joyce et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Targeting the carbohydrates on HIV-1: Interaction of oligomannose dendrons with human monoclonal antibody 2G12 and DC-SIGN

(2008) S.-K. Wang et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Synthetic glycopeptide vaccines combining  -mannan and peptide epitopes induce protection against candidiasis

(2008) H. Xin et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Automated oligosaccharide synthesis

(2007) Peter H. Seeberger   CHEMICAL SOCIETY REVIEWS

Chemical Synthesis of a Glycoprotein Having an Intact Human Complex-Type Sialyloligosaccharide under the Boc and Fmoc Synthetic Strategies

(2007) Naoki Yamamoto et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Oligomannan Synthesis Using Ionic Liquid Supported Glycosylation§

(2007) Ashish K. Pathak et al.   ORGANIC LETTERS