Chemical (neo)glycosylation of biological drugs

2019 FDA drug approvals

(2020) Asher Mullard   NATURE REVIEWS DRUG DISCOVERY

Artificial Glycoproteins as a Scaffold for Targeted Drug Therapy

(2020) Kenward Vong et al.   Small

Direct Synthesis of para-Nitrophenyl Glycosides from Reducing Sugars in Water

(2020) Xin Qiu et al.   ORGANIC LETTERS

Recent Progress in the Synthesis of Homogeneous Erythropoietin (EPO) Glycoforms

(2020) Yuxin Wang et al.   CHEMBIOCHEM

Efficient generation of thiolate sugars from glycosyl Bunte salts and its application to S-glycoside synthesis

(2020) Yasuhiro Meguro et al.   TETRAHEDRON LETTERS

Protein Glycoengineering: An Approach for Improving Protein Properties

(2020) Bo Ma et al.   Frontiers in Chemistry

Total Synthesis of Glycosylated Human Interferon-γ

(2020) Xiaoyi Wang et al.   ORGANIC LETTERS

An atlas of O-linked glycosylation on peptide hormones reveals diverse biological roles

(2020) Thomas D. Madsen et al.   Nature Communications

Chemical Synthesis of an Erythropoietin Glycoform Having a Triantennary N-Glycan: Significant Change of Biological Activity of Glycoprotein by Addition of a Small Molecular Weight Trisaccharide

(2020) Yuta Maki et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Consequences of the Endogenous N-Glycosylation of Human Ribonuclease 1

(2019) Valerie Ressler et al.   BIOCHEMISTRY

2018 FDA drug approvals

(2019) Asher Mullard   NATURE REVIEWS DRUG DISCOVERY

Synthesis of erythropoietins site‐specifically conjugated with complex‐type N‐glycans

(2019) Katharina Streichert et al.   CHEMBIOCHEM

Native Chemical Ligation and Extended Methods: Mechanisms, Catalysis, Scope, and Limitations

(2019) Vangelis Agouridas et al.   CHEMICAL REVIEWS

O-GlcNAc Engineering of GPCR Peptide-Agonists Improves Their Stability and in Vivo Activity

(2019) Paul M. Levine et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Going Native: Synthesis of Glycoproteins and Glycopeptides via Native Linkages To Study Glycan-Specific Roles in the Immune System

(2019) Mikkel H. S. Marqvorsen et al.   BIOCONJUGATE CHEMISTRY

Total Chemical Synthesis of a Nonfibrillating Human Glycoinsulin

(2019) Mohammed Akhter Hossain et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A double-click approach to the protecting group free synthesis of glycoconjugates

(2018) S. R. Alexander et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

The impact of O-glycan chemistry on the stability of intrinsically disordered proteins

(2018) Erica T. Prates et al.   Chemical Science

Facile chemoenzymatic synthesis of Lewis a (Lea) antigen in gram-scale and sialyl Lewis a (sLea) antigens containing diverse sialic acid forms

(2018) Nova Tasnima et al.   CARBOHYDRATE RESEARCH

The Mechanistic Impact of N-Glycosylation on Stability, Pharmacokinetics, and Immunogenicity of Therapeutic Proteins

(2018) Qun Zhou et al.   JOURNAL OF PHARMACEUTICAL SCIENCES

Glycosylation of IgG-Fc: a molecular perspective

(2017) Masato Kiyoshi et al.   INTERNATIONAL IMMUNOLOGY

Protecting group free synthesis of glycosyl thiols from reducing sugars in water; application to the production of N-glycan glycoconjugates

(2017) S. R. Alexander et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Glycosyl Bunte Salts: A Class of Intermediates for Sugar Chemistry

(2017) Yasuhiro Meguro et al.   ORGANIC LETTERS

Glycosylation engineering of therapeutic IgG antibodies: challenges for the safety, functionality and efficacy

(2017) Yusuke Mimura et al.   Protein & Cell

Stabilizing the CH2 Domain of an Antibody by Engineering in an Enhanced Aromatic Sequon

(2016) Wentao Chen et al.   ACS Chemical Biology

Chemoenzymatic Synthesis of a Phosphorylated Glycoprotein

(2016) Pragya Priyanka et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

One-Pot Synthesis of Unprotected Anomeric Glycosyl Thiols in Water for Glycan Ligation Reactions with Highly Functionalized Sugars

(2016) Sebastian Köhling et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Evaluation of the effect of post-translational modification toward protein structure: Chemical synthesis of glycosyl crambins having either a high mannose-type or a complex-type oligosaccharide

(2016) Simone Dedola et al.   BIOPOLYMERS

One-Step Derivatization of Reducing Oligosaccharides for Rapid and Live-Cell-Compatible Chelation-Assisted CuAAC Conjugation

(2016) Takuya Machida et al.   CHEMBIOCHEM

Biological roles of glycans

(2016) Ajit Varki   GLYCOBIOLOGY

The Dependence of Carbohydrate–Aromatic Interaction Strengths on the Structure of the Carbohydrate

(2016) Che-Hsiung Hsu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Materials and methods for delivery of biological drugs

(2016) Alexander N. Zelikin et al.   Nature Chemistry

Synthesis and amylin receptor activity of glycomimetics of pramlintide using click chemistry

(2016) Lauren R. Yule et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Direct aqueous synthesis of cyanomethyl thioglycosides from reducing sugars; ready access to reagents for protein glycosylation

(2016) Stewart R. Alexander et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Chemical synthesis of erythropoietin glycoforms for insights into the relationship between glycosylation pattern and bioactivity

(2016) M. Murakami et al.   Science Advances

Chemically glycosylation improves the stability of an amperometric horseradish peroxidase biosensor

(2015) Griselle Hernández-Cancel et al.   ANALYTICA CHIMICA ACTA

Protein Glycosylation in Cancer

(2015) Sean R. Stowell et al.   Annual Review of Pathology-Mechanisms of Disease

Site-Specific Glycoconjugation of Protein via Bioorthogonal Tetrazine Cycloaddition with a Genetically Encoded trans-Cyclooctene or Bicyclononyne

(2015) Takuya Machida et al.   BIOCONJUGATE CHEMISTRY

Metal-catalyzed Stereoselective and Protecting-group-free Synthesis of 1,2-cis-Glycosides Using 4,6-Dimethoxy-1,3,5-triazin-2-yl Glycosides as Glycosyl Donors

(2015) Tomonari Tanaka et al.   CHEMISTRY LETTERS

Glycosylated Enfuvirtide: A Long-Lasting Glycopeptide with Potent Anti-HIV Activity

(2015) Shuihong Cheng et al.   JOURNAL OF MEDICINAL CHEMISTRY

Carbohydrate–Aromatic Interactions in Proteins

(2015) Kieran L. Hudson et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Rational design of therapeutic mAbs against aggregation through protein engineering and incorporation of glycosylation motifs applied to bevacizumab

(2015) Fabienne Courtois et al.   mAbs

O-GlcNAc modification blocks the aggregation and toxicity of the protein α-synuclein associated with Parkinson's disease

(2015) Nicholas P. Marotta et al.   Nature Chemistry

Targeting protein aggregation for the treatment of degenerative diseases

(2015) Yvonne S. Eisele et al.   NATURE REVIEWS DRUG DISCOVERY

Molecular-scale features that govern the effects of O-glycosylation on a carbohydrate-binding module

(2015) Xiaoyang Guan et al.   Chemical Science

Convergent chemo-enzymatic synthesis of mannosylated glycopeptides; targeting of putative vaccine candidates to antigen presenting cells

(2015) Julie D. McIntosh et al.   Chemical Science

Effects of N-glycosylation on protein conformation and dynamics: Protein Data Bank analysis and molecular dynamics simulation study

(2015) Hui Sun Lee et al.   Scientific Reports

Semisynthesis of Biologically Active Glycoforms of the Human Cytokine Interleukin 6

(2014) Andreas Reif et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Protecting-Group-Free One-Pot Synthesis of Glycoconjugates Directly from Reducing Sugars

(2014) David Lim et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Chemical glycosylation of cytochrome c improves physical and chemical protein stability

(2014) Yamixa Delgado et al.   BMC BIOCHEMISTRY

O-GlcNAc and neurodegeneration: biochemical mechanisms and potential roles in Alzheimer's disease and beyond

(2014) Scott A. Yuzwa et al.   CHEMICAL SOCIETY REVIEWS

“Click” reactions: a versatile toolbox for the synthesis of peptide-conjugates

(2014) Wen Tang et al.   CHEMICAL SOCIETY REVIEWS

The intrinsic and extrinsic effects of N-linked glycans on glycoproteostasis

(2014) Daniel N Hebert et al.   Nature Chemical Biology

Convergent chemoenzymatic synthesis of a library of glycosylated analogues of pramlintide: structure–activity relationships for amylin receptor agonism

(2014) Renata Kowalczyk et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Specificity of O-glycosylation in enhancing the stability and cellulose binding affinity of Family 1 carbohydrate-binding modules

(2014) L. Chen et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

The Winding Pathway to Erythropoietin Along the Chemistry-Biology Frontier: A Success At Last

(2013) Rebecca M. Wilson et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Solid phase synthesis of glycopeptides using Shoda's activation of unprotected carbohydrates

(2013) Alexandre Novoa et al.   CHEMICAL COMMUNICATIONS

Protection-free Synthesis of Alkyl Glycosides under Hydrogenolytic Conditions

(2013) Masaki Ishihara et al.   CHEMISTRY LETTERS

Glycosylation of Pramlintide: Synthetic Glycopeptides that Display In Vitro and In Vivo Activities as Amylin Receptor Agonists

(2013) Yusuke Tomabechi et al.   CHEMISTRY-A EUROPEAN JOURNAL

Structural and Energetic Basis of Carbohydrate–Aromatic Packing Interactions in Proteins

(2013) Wentao Chen et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Erythropoietin Derived by Chemical Synthesis

(2013) P. Wang et al.   SCIENCE

Synthetically defined glycoprotein vaccines: current status and future directions

(2013) Roberto Adamo et al.   Chemical Science

Carbohydrate–Aromatic Interactions

(2012) Juan Luis Asensio et al.   ACCOUNTS OF CHEMICAL RESEARCH

Chemical Synthesis of an Erythropoietin Glycoform Containing a Complex-type Disialyloligosaccharide

(2012) Masumi Murakami et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

At Last: Erythropoietin as a Single Glycoform

(2012) Ping Wang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

N-glycosylation of enhanced aromatic sequons to increase glycoprotein stability

(2012) Joshua L. Price et al.   BIOPOLYMERS

Chemical Synthesis of Homogeneous Human Glycosyl-interferon-β That Exhibits Potent Antitumor Activity in Vivo

(2012) Izumi Sakamoto et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

The impact of glycosylation on monoclonal antibody conformation and stability

(2012) Kai Zheng et al.   mAbs

A “Tag-and-Modify” Approach to Site-Selective Protein Modification

(2011) Justin M. Chalker et al.   ACCOUNTS OF CHEMICAL RESEARCH

Direct Dehydrative Pyridylthio-Glycosidation of Unprotected Sugars in Aqueous Media Using 2-Chloro-1,3-dimethylimidazolinium Chloride as a Condensing Agent

(2011) Naoki Yoshida et al.   Chemistry-An Asian Journal

Glycosylation of the enhanced aromatic sequon is similarly stabilizing in three distinct reverse turn contexts

(2011) J. L. Price et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Protein Native-State Stabilization by Placing Aromatic Side Chains in N-Glycosylated Reverse Turns

(2011) E. K. Culyba et al.   SCIENCE

Methods for converting cysteine to dehydroalanine on peptides and proteins

(2011) Justin M. Chalker et al.   Chemical Science

Glycosylation of Therapeutic Proteins

(2010) Ricardo J. Solá et al.   BIODRUGS

Identification of glycosylated exendin-4 analogue with prolonged blood glucose-lowering activity through glycosylation scanning substitution

(2010) Taichi Ueda et al.   BIOORGANIC & MEDICINAL CHEMISTRY LETTERS

Glycosylation influences on the aggregation propensity of therapeutic monoclonal antibodies

(2010) Veysel Kayser et al.   Biotechnology Journal

Context-Dependent Effects of Asparagine Glycosylation on Pin WW Folding Kinetics and Thermodynamics

(2010) Joshua L. Price et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Perturbing the folding energy landscape of the bacterial immunity protein Im7 by site-specific N-linked glycosylation

(2010) M. M. Chen et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

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

Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality

(2009) Ellen M. Sletten et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

One-step conversion of unprotected sugars to β-glycosyl azides using 2-chloroimidazolinium salt in aqueous solution

(2009) Tomonari Tanaka et al.   CHEMICAL COMMUNICATIONS

Folding of glycoproteins: toward understanding the biophysics of the glycosylation code

(2009) Dalit Shental-Bechor et al.   CURRENT OPINION IN STRUCTURAL BIOLOGY

Efficient Synthesis of Sugar Oxazolines from UnprotectedN-Acetyl-2-amino Sugars by Using Chloroformamidinium Reagent in Water

(2009) Masato Noguchi et al.   JOURNAL OF ORGANIC CHEMISTRY

Chemoenzymatic Synthesis of Glycosylated Glucagon-like Peptide 1: Effect of Glycosylation on Proteolytic Resistance and in Vivo Blood Glucose-Lowering Activity

(2009) Taichi Ueda et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Emerging methods for the production of homogeneous human glycoproteins

(2009) Jamie R Rich et al.   Nature Chemical Biology

The core trisaccharide of an N-linked glycoprotein intrinsically accelerates folding and enhances stability

(2009) S. R. Hanson et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Structural and Biophysical Studies of the Human IL-7/IL-7Rα Complex

(2009) Craig A. McElroy et al.   STRUCTURE

Chemoselective Ligation and Modification Strategies for Peptides and Proteins

(2008) Christian P. R. Hackenberger et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

The Effect of Glycosylation on Interparticle Interactions and Dimensions of Native and Denatured Phytase

(2008) R. Høiberg-Nielsen et al.   BIOPHYSICAL JOURNAL

Facile Conversion of Cysteine and Alkyl Cysteines to Dehydroalanine on Protein Surfaces: Versatile and Switchable Access to Functionalized Proteins

(2008) Gonçalo J. L. Bernardes et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

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

(2008) Yvette van Kooyk et al.   NATURE IMMUNOLOGY

Protecting Group Free Glycosidations Usingp-Toluenesulfonohydrazide Donors

(2008) Anna V. Gudmundsdottir et al.   ORGANIC LETTERS

Effect of glycosylation on protein folding: A close look at thermodynamic stabilization

(2008) D. Shental-Bechor et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA