Chemical remodelling of cell surfaces in living animals

  title={Chemical remodelling of cell surfaces in living animals},
  author={Jennifer A. Prescher and Danielle H. Dube and Carolyn R. Bertozzi},
Cell surfaces are endowed with biological functionality designed to mediate extracellular communication. The cell-surface repertoire can be expanded to include abiotic functionality through the biosynthetic introduction of unnatural sugars into cellular glycans, a process termed metabolic oligosaccharide engineering. This technique has been exploited in fundamental studies of glycan-dependent cell–cell and virus–cell interactions and also provides an avenue for the chemical remodelling of… 

100th Anniversary of Macromolecular Science Viewpoint: Re-Engineering Cellular Interfaces with Synthetic Macromolecules Using Metabolic Glycan Labeling

The potential of using metabolic glycan labeling to install bio-orthogonal reactive cell-surface anchors for the recruitment of synthetic polymers and nanomaterials to cell surfaces is discussed, exploring the expanding therapeutic and diagnostic potential.

Metabolic oligosaccharide engineering: perspectives, applications, and future directions.

Many adhesion and signaling molecules critical for development, as well as surface markers implicated in diseases ranging from cancer to influenza, contain oligosaccharides that modify their

Remodeling of Cellular Surfaces via Fast Disulfide-Thiol Exchange to Regulate Cell Behaviors.

A sequential layer by layer assembly process was developed to grow albumin pro-tein shells on cellular surfaces fixed by disulfide-linked network, in a cytocompatible manner, and was well validated on tumor cell, immune cell, and neutrophils showing its potential universality for most of the cells that are rich in thiols.

Thermally Triggered, Cell-Specific Enzymatic Glyco-Editing: In Situ Regulation of Lectin Recognition and Immune Response on Target Cells.

The proposed method provides an unprecedented opportunity to potentiate the innate immune response of natural killer cells toward target tumor cells through thermally triggered cell-specific desialylation, which paves the way for in vivo glycoimmune-checkpoint-targeted cancer therapeutic intervention.

Chemical Tools for Imaging Glycans in Living Systems

A two-step method to equip glycans with reporter tags for isolation and visualization from living systems known as the chemical reporter strategy is developed.

Recent Chemical Biology Approaches for Profiling Cell Surface Sialylation Status.

This review highlights the recent advancements in chemical biology approaches for profiling cell surface sialyation status and investigates the sialylation status of a specific glycoprotein on the cell surface.

The Applications of Metabolic Glycoengineering

Mammalian cell membranes are decorated by the glycocalyx, which offer versatile means of generating biochemical signals. By manipulating the set of glycans displayed on cell surface, it is vital for

Switchable Enzymatic Accessibility for Precision Cell-Selective Surface Glycan Remodeling.

It is shown that this level of SEA regulation enables initial guided enzyme delivery to target cell surface for subsequent cell-specific glycan remodeling, thus providing a temporally and spatially controlled tool for tuning the glycosylation architectures.

Azido Sialic Acids Can Modulate Cell‐Surface Interactions

This work probes the tolerance of numerous sialic acid-binding proteins for unnatural modification to their cell-surface ligands, a method termed “metabolic oligosaccharide engineering”.



Engineering chemical reactivity on cell surfaces through oligosaccharide biosynthesis.

The versatility of this technology was demonstrated by an example of selective drug delivery, where cells were decorated with biotin through selective conjugation to ketone groups, and selectively killed in the presence of a ricin A chain-avidin conjugate.

Constructing azide-labeled cell surfaces using polysaccharide biosynthetic pathways.

Cell surface engineering by a modified Staudinger reaction.

A chemical transformation that permits the selective formation of covalent adducts among richly functionalized biopolymers within a cellular context is presented and should permit its execution within a cell's interior, offering new possibilities for probing intracellular interactions.

Metabolic functionalization of recombinant glycoproteins.

Glycoproteins are essential for cellular communication and are the most rapidly growing class of therapeutic agents. Chemical modification of glycoproteins has been employed to improve their in vivo

Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation.

This study investigates the conversion of a panel of azide-functionalized mannosamine and glucosamine derivatives into cell-surface sialosides and demonstrates that the cell- surface Staudinger ligation is compatible with hydrazone formation from metabolically introduced ketones.

Intracellular trafficking of cell surface sialoglycoconjugates.

Biochemical Engineering of Cell Surface Sialic Acids Stimulates Axonal Growth

It is hypothesized that transcription could be modulated by the unnatural CMP-N-propanoylneuraminic acid and that sialic acid activation might be a general tool to regulate cellular functions, such as neurite outgrowth.

A chemical approach for identifying O-GlcNAc-modified proteins in cells

A chemical strategy directed toward identifying O-GlcNAc-modified proteins from living cells or proteins modified in vitro is described, in vitro, that each enzyme in the hexosamine salvage pathway, and the enzymes that affect this dynamic modification, tolerate analogues of their natural substrates in which the N-acyl side chain has been modified to bear a bio-orthogonal azide moiety.

Metabolic oligosaccharide engineering as a tool for glycobiology.

Differential Effects of Unnatural Sialic Acids on the Polysialylation of the Neural Cell Adhesion Molecule and Neuronal Behavior*

N-butanoylmannosamine blocked polysialylation of NCAM and significantly reduced neurite outgrowth comparable with enzymatic removal of PSA by endoneuraminidases, and subtle structural differences in PSA resulting from the incorporation of SiaProp residues do not alter the antiadhesive properties of polysIALylated NCAM.