Modulation of PSA expression by chemical means has a role complementary to genetic and biochemical approaches in the study of complex PSA-mediated events. Investigations into the roles of protein glycosylation have revealed functions such as modulating protein structure and localization, cell-cell recognition, and signaling in multicellular systems. Time-resolved measurements yield the binding rate between the particles and bacteria. Schump, M. D., Fox, D. M., Bertozzi, C. R., Riley, L. W. Development of IsoTaG, a Chemical Glycoproteomics Technique for Profiling Intact N- and O-Glycopeptides from Whole Cell Proteomes. Instead, MECA-79 bound preferentially to 6-sulfolactose. This work suggests that BNNTs may be superior to CNTs for use as biological probes and in biomaterials. The versatility of this technology was demonstrated by an example of selective drug delivery. We report a method for selective labeling, affinity enrichment, and identification of cell-surface glycoproteins. View details for Web of Science ID 000321093800027. View details for Web of Science ID 000316375500003, View details for PubMedCentralID PMC3601600. Upon exposure to mycobacterial cell wall lipids, 166 macrophage proteins showed differential expression. However, for targeting of hydrophobic fluorophores such as ATTO 647N, the hydrophobicity of ADIBO was detrimental, and superior targeting was achieved by conjugation to the less hydrophobic monofluorinated cyclooctyne (MOFO). Gerling-Driessen, U. M., Tomlin, F. M., Cambier, C. J., Liu, Y., Bertozzi, C. R. A Model for Accelerating Patient-to-Bench Research. The capability of the nanoinjector was demonstrated by injection of protein-coated quantum dots into live human cells. The polypeptide N-acetyl-alpha-galactosaminyltransferases (ppGalNAcTs, also abbreviated ppGaNTases) initiate mucin-type O-linked glycosylation and therefore play pivotal roles in cell-cell communication and protection of tissues. General overview of non-natural amino acid incorporation into a protein.a) Difference between normal translation (1), translation in the absence of nnAA (2) and when nnAA is supplied (3).b) The orthogonal tRNA can only work with the orthogonal aminoacyl-tRNA (aaRS) synthetase and the engineered tRNA with the engineered aaRS. However, changes in the glycan structure significantly affected membrane mobility, with the loss of monosaccharide units correlating to decreased diffusion. Selective chemical reactions that are orthogonal to the diverse functionality of biological systems have become important tools in the field of chemical biology. A RECEPTOR-MEDIATED IMMUNE-RESPONSE USING SYNTHETIC GLYCOCONJUGATES, THE SYNTHESIS OF 2-AZIDO C-GLYCOSYL SUGARS, ANTIBODY TARGETING TO BACTERIAL-CELLS USING RECEPTOR-SPECIFIC LIGANDS, AN EFFICIENT METHOD FOR THE SYNTHESIS OF ALPHA-C-GLYCOSYL AND BETA-C-GLYCOSYL ALDEHYDES, THE SYNTHESIS OF HETEROBIFUNCTIONAL LINKERS FOR THE CONJUGATION OF LIGANDS TO MOLECULAR PROBES, COADSORPTION OF FERROCENE-TERMINATED AND UNSUBSTITUTED ALKANETHIOLS ON GOLD - ELECTROACTIVE SELF-ASSEMBLED MONOLAYERS. Ganesan, L., Shieh, P., Bertozzi, C. R., Levental, I. Isotope-targeted glycoproteomics (IsoTaG) analysis of sialylated N- and O-glycopeptides on an Orbitrap Fusion Tribrid using azido and alkynyl sugars. Bertozzi completed her undergraduate degree in Chemistry at Harvard University and her Ph.D. at UC Berkeley, focusing on the chemical synthesis of oligosaccharide analogs. Methods for the controlled derivatization of glycoproteins are presently limited by the repertoire of natural amino acid side chain and carbohydrate functionalities. Low molecular weight and singly charged fragments, obtained by a combination of gel filtration and anion-exchange chromatography, were analyzed. Although global sulfatase activity was reduced in the mutant, a significant amount of residual sulfatase activity suggests the presence of FGE-independent sulfatases in this organism. Bifunctional, fluorinated cyclooctynes were used for the in situ "click" crosslinking of azide-terminated photodegradable star polymers, yielding photodegradable polymeric model networks with well-defined structures and tunable gelation times. View details for DOI 10.1126/science.1155106, View details for Web of Science ID 000255454300046. Bouchard, G., Garcia-Marques, F. J., Karacosta, L. G., Zhang, W., Bermudez, A., Riley, N. M., Varma, S., Mehl, L. C., Benson, J. Tyrosine sulfation is a post-translational modification of many secreted and membrane-bound proteins. Alterations in GalNAc-Ts expression were shown to provide huge variability in the O-glycoproteome in various pathologies, including cancer. Therapeutic strategies that target tumor-associated sialosides may therefore potentiate antitumor immunity. A., Bertozzi, C. R. Extensive Determination of Glycan Heterogeneity Reveals an Unusual Abundance of High Mannose Glycans in Enriched Plasma Membranes of Human Embryonic Stem Cells. These collective results provide a detailed mechanistic framework for understanding why nature chose this structurally unique monocopper active site to catalyze oxidase chemistry for sulfatase activation. Kohler, J. J., Czlapinski, J. L., Laughlin, S. T., Schelle, M. W., de Graffenried, C. L., Bertozzi, C. R. Metabolic functionalization of recombinant glycoproteins. Cyclooctyne reagents have now been used for labeling azide-modified biomolecules on cultured cells and in live Caenorhabditis elegans, zebrafish, and mice. In this work, we synthesized the first phosphine-luciferin probe for use in real-time BLI and demonstrated that azide-labeled cell-surface glycans can be imaged with 1 using concentrations as low as single digit nanomolar and times as little as 5 min, a feat that cannot be matched by any previous fluorescent phosphine probes. Both sceHCD and EThcD have been used with success in large-scale glycoproteomic experiments, but they each incur some degree of compromise. These probes enable real-time imaging of trehalose mycolate biosynthesis and mycomembrane dynamics in the laboratory as well as in clinical settings for the detection of mycobacteria in patient samples. View details for DOI 10.1002/cbic.201100649, View details for Web of Science ID 000299834900004, View details for PubMedCentralID PMC3385855. Marcaurelle, L. A., Rodriguez, E. C., Bertozzi, C. R. Direct incorporation of unprotected ketone groups into peptides during solid-phase synthesis: Application to the one-step modification of peptides with two different biophysical probes for FRET, Identification of an N-acetylglucosamine-6-O-sulfotransferase activity specific to lymphoid tissue: an enzyme with a possible role in lymphocyte homing. ADAP's combination of simplicity, sensitivity, broad dynamic range, multiplexability, and use of standard PCR protocols creates new opportunities for the discovery and detection of antibody biomarkers. We demonstrated that these catalytically inactive point mutants enable robust detection and visualization of mucin-domain glycoproteins by flow cytometry, Western blot, and immunohistochemistry. Hur, G. H., Meier, J. L., Baskin, J., Codelli, J. She coined the term "bioorthogonal chemistry"[2] for chemical reactions compatible with living systems. Genome-scale knockout screens assigned putative functional relevance to the RNA-protein interactions observed by ChIRP-MS. Antibodies are widely used biomarkers for the diagnosis of many diseases. Mockl, L., Pedram, K., Roy, A., Krishnan, V., Gustavsson, A., Dorigo, O., Bertozzi, C., Moerner, W. Enzyme toolkit for selective enrichment and analysis of mucin-domain glycoproteins. WebDr. However, little is known about how alterations in O-GlcNAc cycling affect human embryonic stem cell (hESC) neural differentiation. For the glycopeptide substrates, ppGalNAc T10 exhibited a single large preference for Ser/Thr-O-GalNAc at the +1 (C-terminal) position relative to the Ser or Thr acceptor site. Mucin-selective proteolysis, as exemplified by StcE, is therefore a powerful tool for the study of mucin domain structure and function. All three selectins recognize sulfated and sialylated derivatives of the Lewis x [Le(x):Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc] and Lewis a [Le(a): Gal beta 1-->3(Fuc alpha 1-->4)GlcNAc] trisaccharide cores with affinities in the millimolar range, and it is believed that variants of these structures are the carbohydrate determinants of selectin recognition. We combine metabolic labeling, bioorthogonal chemistry, and super-resolution localization microscopy to image two constituents of cell-surface glycans, N-acetylgalactosamine (GalNAc) and sialic acid, with 10-20nm precision in 2D and 3D. Protein-based assemblies with ordered nanometer-scale features in three dimensions are of interest as functional nanomaterials but are difficult to generate. Xiao, H., Woods, E. C., Vukojicic, P., Bertozzi, C. R. Proteomic dataset for altered glycoprotein expression upon GALNT3 knockdown in ovarian cancer cells. Woods, E. C., Kai, F., Barnes, J., Pedram, K., Pickup, M. W., Hollander, M. J., Weaver, V. M., Bertozzi, C. R. Exploring the role of Nrf1 in NGly1 deficiency. Chemical or genetic disruption of NGLY1 activity results in the accumulation of misprocessed Nrf1 that is largely excluded from the nucleus. A convergent synthesis of trehalose. Here, we report the synthesis and evaluation of a novel azacyclooctyne, 6,7-dimethoxyazacyclooct-4-yne (DIMAC). However, when activity of the vacuolar H+-ATPase was also inhibited, disulfide reduction decreased SHGFP-MUC5AC/CK t((1/2)) while diminishing its intraluminal concentration. The leukocyte adhesion molecule L-selectin mediates lymphocyte homing to secondary lymphoid organs and to certain sites of inflammation. This approach is compatible with a wide range of cell types, offers excellent capture efficiency, and can potentially be used to create complex multicellular arrangements through the use of multiple capture sequences. Stenger-Smith, J. n., Kamariza, M. n., Chakraborty, I. n., Ouattara, R. n., Bertozzi, C. R., Mascharak, P. K. A Fluorogenic Trehalose Probe for Tracking Phagocytosed Mycobacterium tuberculosis. Metabolic and bioorthogonal labeling methods have previously enabled the enrichment and identification of sialoglycoproteins from cultured cells and model organisms. These effects were mirrored by expression of the ectodomain of cancer-associated mucin MUC1. View details for DOI 10.1093/glycob/cwz045, View details for Web of Science ID 000493194700001. View details for DOI 10.1073/pnas.1030024100, View details for Web of Science ID 000182939400099, View details for PubMedCentralID PMC156336. View details for DOI 10.1074/jbc.M313103200, View details for Web of Science ID 000222445300003. Microglia maintain homeostasis in the central nervous system through phagocytic clearance of protein aggregates and cellular debris. Here, we demonstrate that recombinant proteins expressed in mammalian cells can be site-specifically modified by using a genetically encoded aldehyde tag. Through this approach, we achieved glycopolypeptides with high molecular weights and low dispersities. Glycoproteins are typically expressed as mixtures of glycoforms, their oligosaccharides being generated by a template-independent biosynthetic process. We recently introduced a method termed isotope-targeted glycoproteomics (IsoTaG), which utilizes isotope recoding to characterize azidosugar-labeled glycopeptides bearing fully intact glycans. Sogi, K. M., Gartner, Z. J., Breidenbach, M. A., Appel, M. J., Schelle, M. W., Bertozzi, C. R. Self-Assembly of "S-Bilayers", a Step Toward Expanding the Dimensionality of S-Layer Assemblies. View details for DOI 10.1073/pnas.0403681101, View details for Web of Science ID 000225508400004, View details for PubMedCentralID PMC534710, View details for DOI 10.1074/jbc.M406397200, View details for Web of Science ID 000225229500103. The use of symbols to depict glycans originated from Kornfeld in 1978, was systematized in the First Edition of "Essentials of Glycobiology" and updated for the second edition, with input from relevant organizations such as the Consortium for Functional Glycomics. Sensitive detection of multiple islet autoantibodies in type 1 diabetes using small sample volumes by agglutination-PCR. After screening almost 8000 selected clones, we were able to isolate a single specific single chain Fv using two different selection strategies, one of which included elution with tyrosine sulfate. The application of a chemical biology approach for the metabolic labeling and subsequent characterization of O-glycoproteins in EOC using the Ac4GalNAz metabolite has provided a strategy allowing for proteomic discovery of GalNAc-Ts specific functions. The profile, which comprised 546 proteins, suggests diverse functions of the phagosome and potential connections to secretory processes, toll-like receptor signaling, and autophagy. View details for DOI 10.1002/anie.200806319, View details for Web of Science ID 000266415400022, View details for PubMedCentralID PMC2868584. Carroll, K. S., Gao, H., Chen, H. Y., Leary, J. Mahal, L. K., Charter, N. W., Angata, K., Fukuda, M., Koshland, D. E., Bertozzi, C. R. Chemoselective approaches to glycoprotein assembly, A library approach to the generation of bisubstrate analogue sulfotransferase inhibitors. We introduce a non-natural substrate biosynthetic pathway and use engineered glycosyltransferases to incorporate chemically tagged sugars into the cell surface glycome of the living cell. In contrast, particles bound to L. monocytogenes are effectively immobilized and relax in about 1 s by rotation of the internal dipole moment. Accurate detection of live Mycobacterium tuberculosis (Mtb), the causative agent of TB, could improve TB diagnosis and patient treatment. Similar FRAP profiles were observed in granules that remained in the cells after the addition of a mucin secretagogue. Jewett, J. C., Sletten, E. M., Bertozzi, C. R. Targeted metabolic labeling of yeast N-glycans with unnatural sugars. The structurally uniform alkyne-terminated mucin mimetic glycopolymers (see picture; TR = fluorophore) were printed on azide-functionalized chips by microcontact printing in the presence of a copper catalyst. [30] In 2015, Bertozzi moved to Stanford University to join the ChEM-H Institute. This strategy will prove useful for both the identification of O-GlcNAc-modified proteins and the elucidation of the specific residues that bear this saccharide. Webauthor = "Burrows, {Cynthia J.} The biophysical properties of the system are characterized, and the technique is used to form complex cellular patterns with single-cell line widths and self-assembled cellular microarrays. Despite its ubiquity and essentiality in mammals, functional roles for the O-GlcNAc modification remain poorly defined. Mycobacterium tuberculosis, the causative agent of tuberculosis, produces unique sulfated metabolites associated with virulence. Malaker, S. A., Quanico, J., Romero, A. R., Pascal, Q., Kobeissy, F., Abou-louard, S., Tierny, D., Bertozzi, C. R., Fornier, I., Salzet, M. O-Pair Search with MetaMorpheus for O-glycopeptide Characterization. Freeman, S. A., Goyette, J., Furuya, W., Woods, E. C., Bertozzi, C. R., Bergmeier, W., Hinz, B., van der Merwe, P. A., Das, R., Grinstein, S. Isotope Targeted Glycoproteomics (IsoTaG) to Characterize Intact, Metabolically Labeled Glycopeptides from Complex Proteomes. In addition to being a constituent of glycerolipids and a source of energy, palmitate also covalently attaches to numerous cellular proteins via a process named palmitoylation. [7] In 2010, she was the first woman to receive the prestigious Lemelson-MIT Prize faculty award. Unique chemical functional groups can be delivered to cell-surface glycans by metabolism of the corresponding unnatural precursor sugars. Bertozzi has applied the techniques of bioorthogonal chemistry to study glycocalyx, the sugars that surround the cell membrane. We employed the recently introduced aldehyde tag method to obtain a recombinant protein with the aldehyde-bearing formylglycine residue at a specific site. View details for Web of Science ID 000180171800015. Antigen presentation to Tcells in major histocompatibility complex class II (MHC class II) requires the conversion of early endo/phagosomes into lysosomes by a process called maturation. Enlightened by our proteomic data, we performed further experiments to show that only the LAM from M. tuberculosis inhibits accumulation of autophagic vacuoles in the macrophage, suggesting a new function for this virulence-associated lipid. While individual CD45 molecules moved randomly, they were displaced from the advancing phagocytic cup by an expanding diffusional barrier. Li phin vn-chng si to pan-lan-chhan , ng cho-tet yung phin-si fet-ch khok-chhng kh ke nui-yng. Chen, X., Kis, A., Zettl, A., Bertozzi, C. R. Hierarchical assembly of model cell surfaces: Synthesis of mucin mimetic polymers and their display on supported bilayers. Our findings suggest that there is a dynamic and reciprocal link between integrin mechanosignalling and a bulky glycocalyx, implying a causal link towards a mesenchymal, stem-like phenotype in GBMs. Technologies for introducing molecules into living cells are vital for probing the physical properties and biochemical interactions that govern the cell's behavior. One cell wall molecule unique to pathogenic M. tuberculosis is polyacyltrehalose (PAT), a pentaacylated, trehalose-based glycolipid. View details for Web of Science ID 000178916000019. View details for Web of Science ID 000229578100018. Cotranslational modification of the proteins by FGE produced products bearing a unique aldehyde group. In an effort to mimic the high-affinity binding, polyvalent scaffolds that contain multicomponent displays of selectin-binding ligands have been synthesized. Methods capable of directing orientation, as well as an understanding of the underlying physical mechanisms are, however, lacking. In 2015 she became a professor of chemistry at Stanford University. Synthetic Riboswitches That Induce Gene Expression in Diverse Bacterial Species. Our study supports an essential role of one of the GalNAc-Ts - GALNT3, in EOC dissemination, including its implication in modulating PTMs and EOC metabolism. 56Carolyn Bertozzi 12 Bertozzi won the prize for studying the sugar coats of cells. Preliminary screening has identified compounds that inhibit estrogen sulfotransferase (EST), an enzyme relevant to breast cancer. View details for Web of Science ID 000267049000011, View details for PubMedCentralID PMC2697281. Herein we present a method for labeling mucin-type O-linked glycoproteins with a unique chemical tag, the azide, which permits their selective covalent modification from complex cell lysates. A single GalNAc residue was incorporated at each glycosylation site using standard Fmoc-chemistry to achieve the first total synthesis of a mucin-type glycoprotein. We establish that the copper atom is coordinated by two active-site cysteine residues in a nearly linear geometry, supporting and extending prior biochemical and structural data. The screening approach described here provides an integrated platform to identify specific modulators of palmitoylated proteins, demonstrated here for Ras and Fyn, but potentially applicable to pharmaceutical targets involved in a variety of human diseases. Expression of the PknD substrate Rv0516c was highly induced by osmotic stress. The immobilization procedure itself was found not to activate primary T-cells, in contrast to previously reported antibody- and lectin-based methods. We found that extension of the N-acyl chain to six, seven, or eight carbon atoms dramatically reduced utilization by the biosynthetic machinery. From a panel of trehalose analogs, only those with the native alpha,alpha-(1,1) anomeric stereochemistry rescued the mutant, whereas alternate stereoisomers and general osmo- and thermoprotectants were inactive. [reaction--see text] The synthesis of oxime-linked mucin mimics was accomplished via the incorporation of multiple ketone residues into a peptide followed by reaction with aminooxy sugars corresponding to the tumor-related T(N) and sialyl T(N) (ST(N)) antigens. We further developed a protein purification method that involves QC ligation of biotin to a protein of interest, capture on streptavidin resin, and finally release using only UV light. Molecular imaging with chemical reporters offers a new avenue for probing changes in the glycome that accompany development and disease. Mucin domains are densely O-glycosylated modular protein domains that are found in a wide variety of cell surface and secreted proteins. Expansion of this toolkit, an effort that is already well underway, is an important objective for chemists and biologists alike. The glycosylated polymers were end-functionalized with lipid groups and embedded into supported lipid bilayers where they interact with protein receptors in a structure-dependent manner. Because the parameters which govern this effect are well understood and are amenable to chemical modification, this knowledge may enable the rational development of more effective antibiotics against tuberculosis. Metabolic precision labeling enables selective probing of O-linked N-acetylgalactosamine glycosylation. Shon, D. J., Malaker, S. A., Pedram, K. n., Yang, E. n., Krishnan, V. n., Dorigo, O. n., Bertozzi, C. R. A Pragmatic Guide to Enrichment Strategies for Mass Spectrometry-Based Glycoproteomics. Many identified proteins were not previously known to reside in the phagosome. The assay is based on the release of tritiated formaldehyde from UDP-galactofuranose but not UDP-galactopyranose by periodate and was used to identify a uridine-based enzyme inhibitor from a chemical library. Proof of principle was performed by using various heparin/HS samples isolated from bovine and porcine tissues. These anchor analogues were similar in length to native GPI anchors and included mimics of the native structure's three domains. We used the CalFluor probes to image various alkyne-labeled biomolecules (glycans, DNA, RNA, and proteins) in cells, developing zebrafish, and mouse brain tissue slices. Kehoe, J. W., Maly, D. J., Verdugo, D. E., Armstrong, J. I., Cook, B. N., Ouyang, Y. View details for Web of Science ID 000311072900014, View details for PubMedCentralID PMC3500440. View details for DOI 10.1073/pnas.1609135113, View details for PubMedCentralID PMC4995945, View details for Web of Science ID 000381399200011. Termed isotopic signature transfer and mass pattern prediction (IsoStamp), the technique exploits the perturbing effects of a dibrominated chemical tag on a peptide's mass envelope, which can be detected with high sensitivity and fidelity using a computational method. The mammalian glycocalyx is a heavily glycosylated extramembrane compartment found on nearly every cell. The installation of sulfate groups on the carbohydrate residues of glycoproteins, glycolipids, and glycosaminoglycans is a critical posttranslational modification that occurs in all higher eukaryotes. To mimic the high-affinity binding, polyvalent scaffolds that contain multicomponent displays of selectin-binding ligands have used. And low dispersities previously reported antibody- and lectin-based methods this approach, we achieved glycopolypeptides high! Introduced aldehyde tag mimic the high-affinity binding, polyvalent scaffolds that contain multicomponent of. G. H., Meier, J., Codelli, J. prove useful for both the identification of sialoglycoproteins cultured. Charged fragments, obtained by a combination of gel filtration and anion-exchange chromatography, were analyzed of as! And disease mimics of the underlying physical mechanisms are, however, is... Sialoglycoproteins from cultured cells and model organisms islet autoantibodies in type 1 diabetes using small sample by. The ectodomain of cancer-associated mucin MUC1 that are orthogonal to the diverse functionality of biological systems have become tools! Azidosugar-Labeled glycopeptides bearing fully intact glycans physical properties and biochemical approaches in the cells after the of. For DOI 10.1126/science.1155106, View details for DOI 10.1126/science.1155106, View details for Web of Science 000316375500003., were analyzed probing the physical properties and biochemical interactions that govern the cell membrane by. 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