WebBio BIO Professor Carolyn Bertozzi's research interests span the disciplines of chemistry and biology with an emphasis on studies of cell surface sugars important to human health and disease. Some members of the family prefer previously gly co sylated peptides (ppGalNAc T7 and T10), whereas others are inhibited by neighboring gly co sy la tion (ppGalNAc T1 and T2). Investigation of their function has been greatly assisted by sources of homogeneous material. These data provide strong evidence that Stf0 carries out the first committed step in the biosynthesis of SL-1 and establish a system for probing the role of SL-1 in M. tuberculosis infection. View details for DOI 10.1021/jacs.6b03861, View details for PubMedCentralID PMC5327792, View details for DOI 10.1021/acscentsci.6b00224, View details for PubMedCentralID PMC4999963. The GlcNAc-6-sulfotransferases are a family of Golgi-resident enzymes that modulate glycan function. Luchansky, S. J., Yarema, K. J., Takahashi, S., Bertozzi, C. R. Synthesis of thioether-linked analogues of the 2,3-sialyl-TF and MECA-79 antigens: Mucin-type glycopeptides associated with cancer and inflammation. Here we present a unified design, based on the principle of photoinduced electron transfer, to access a panel of highly fluorogenic azide probes that are activated by conversion to the corresponding triazoles via click chemistry. This system thus constitutes an AND-type molecular logic gate that reports on the simultaneous presence of H(2)O(2) and caspase 8 activity. GlcNAc6ST-2 is a member of a family of related enzymes that act on similar carbohydrate substrates in vitro but discrete glycoproteins in vivo. The process of generating aldehyde-tagged protein followed by chemical conjugation and purification takes 20 d. View details for DOI 10.1038/nprot.2012.045, View details for Web of Science ID 000304720700005, View details for PubMedCentralID PMC3498491. View details for DOI 10.1073/pnas.0610634104, View details for Web of Science ID 000245256700066, View details for PubMedCentralID PMC1829275. We identified and characterized a conserved mycobacterial sulfotransferase, Stf0, which generates the T2S moiety of SL-1. Shon, D., Malaker, S. A., Pedram, K., Yang, E., Krishnan, V., Dorigo, O., Bertozzi, C. R. On-tissue microscale glycoproteomics and N-glycan imaging reveal global dysregulation of canine glioma glycoproteomic landscape. GST-5 has recently been characterized as a novel GalNAc 6-O-sulfotransferase termed chondroitin 6-sulfotransferase-2 (Kitagawa, H., Fujita, M., Itio, N., and Sugahara K. (2000) J. Biol. Here we investigate the behavior of these GPI-protein analogs in living cells. The deep structural analysis enabled by this new method will enable future mechanistic studies on the biological significance of high mannose glycans on stem cell membranes and provide a general tool to examine cell surface glycosylation. View details for DOI 10.1146/annurev.biochem.71.110601.135334, View details for Web of Science ID 000177352600021. The group was deliberately composed not only of individuals with a current research emphasis in the glycosciences, but also of many experts from other fields, who evinced a strong interest in being involved in the discussions. Protein-carbohydrate interactions are known to mediate cell-cell recognition and adhesion events. Hudak, J. E., Canham, S. M., Bertozzi, C. R. Osmosensory signaling in Mycobacterium tuberculosis mediated by a eukaryotic-like Ser/Thr protein kinase. This Account summarizes chemoselective approaches for assembling homogeneous glycoconjugates that attempt to reduce the barriers to their synthesis. Here we report that a truncated S-layer protein assembles into stable bilayers, which we characterized using cryogenic-electron microscopy, tomography, and X-ray spectroscopy. Ac4GalNAz treatment labeled the surface of healthy mouse corneas, leaving most cells viable, and bacteria preferentially associated with GalNAz-labeled regions. Tools that can track the replication status of viable Mtb cells within macrophages are vital for the elucidation of host-pathogen interactions. In addition, we have redefined the substrate specificity of the B. subtilis CysH, formerly designated a PAPS reductase, as an APS reductase, based on its ability to complement a mutant E. coli strain deficient in APS kinase. The sulfite generated in this reaction is utilized in bacteria and plants for the eventual production of essential biomolecules such as cysteine and coenzyme A. Genome-wide CRISPR screens reveal a specific ligand for the glycan-binding immune checkpoint receptor Siglec-7. Importantly, we show that mmpL8 mutants are attenuated for growth in a mouse model of tuberculosis. View details for Web of Science ID 000187945400003. These O-azidoacetylglucosamine-modified proteins can be covalently derivatized with various biochemical probes at the site of protein glycosylation by using the Staudinger ligation. A., Sun, J., Iram, T., Bonanno, L., Li, L., Lee, D. P., Morgens, D. W., Yang, A. C., Shuken, S. R., Gate, D., Scott, M., Khatri, P., Luo, J., Bertozzi, C. R., Bassik, M. C., Wyss-Coray, T. Towards Mycobacterium tuberculosis detection at the point-of-care: solvatochromic probes permits the detection of mycobacteria within minutes, Orthogonal enzyme/substrate engineering to profile biological substrates of glycosyltransferases, Glyco-immune modulation in the tumor microenvironment, Formylglycine-generating enzyme binds substrate directly at a mononuclear Cu(I) center to initiate O-2 activation. Circumventing the steps of purification from native cell membranes, this methodology facilitates the reconstitution of membrane-associated proteins. A., Dube, D. H., Bertozzi, C. R. Identification, function and structure of the mycobacterial sulfotransferase that initiates sulfolipid-1 biosynthesis. The absence of activity on the trisaccharide Gal beta 1-->6Gal alpha-R indicates a requirement for a substrate with a terminal GlcNAc residue, suggesting that sulfation precedes further biosynthetic assembly of L-selection ligands. Using an in vitro biochemical assay, we confirmed that Rv3406 is a sulfatase with a preference for alkyl sulfate substrates similar to those processed by AtsK. These receptors have attracted great attention in recent years due to their participation in a number of acute and chronic inflammatory diseases. Finally, we showed that BNNTs can deliver DNA oligomers to the interior of cells with no apparent toxicity. The staggering complexity of glycans renders their analysis extraordinarily difficult, particularly in living systems. However, a detailed structural analysis of S881 has remained elusive. de Graffenried, C. L., Laughlin, S. T., Kohler, J. J., Bertozzi, C. R. An inhibitor of O-glycosylation induces apoptosis in NIH3T3 cells and developing mouse embryonic mandibular tissues (Retracted Article. Measurements from the ADAP assay were compared to radioassay to determine correlation, concordance, agreement, clinical sensitivity and specificity. The galectin family of glycan-binding proteins is thought to mediate many cellular processes by oligomerizing cell surface glycoproteins and glycolipids into higher-order aggregates. High mannose glycans are not commonly presented on the surfaces of mammalian cells or in serum yet may play important roles in stem cell biology. Our method imparts N-glycopeptide mass envelopes with a pattern that is computationally distinguishable from background ions. Barnes, J., Kaushik, S., Bainer, R. O., Sa, J. K., Woods, E. C., Kai, F., Przybyla, L., Lee, M., Lee, H., Tung, J. C., Maller, O., Barrett, A. S., Lu, K. V., Lakins, J. N., Hansen, K. C., Obernier, K., Alvarez-Buylla, A., Bergers, G., Phillips, J. J., Nam, D., Bertozzi, C. R., Weaver, V. M. Glycosyltransferase bump-hole engineering to dissect mucin-type O-glycosylation in the living cell. The design principles embodied in coumBARAC establish a platform for generating fluorogenic cyclooctynes suited for biological imaging. An essential step in this pathway is the activation of sulfate through adenylation by the enzyme ATP sulfurylase (ATPS), forming adenosine 5'-phosphosulfate (APS). Phagocytosis is the central process by which macrophage cells internalize and eliminate infectious microbes as well as apoptotic cells. In the mouse genome we have found a homologous ORF that predicts a novel murine GlcNAc 6-O-sulfotransferase with 88% identity to the human enzyme. Tian, E., Ten Hagen, K. G., SHUM, L., Hang, H. C., Imbert, Y., Young, W. W., Bertozzi, C. R., Tabak, L. A. Thus, this versatile strategy can elucidate features of human biology that control the pathogenesis of clinically relevant viruses. View details for DOI 10.1073/pnas.0437851100, View details for Web of Science ID 000181675200023, View details for PubMedCentralID PMC152251. This review presents an overview of techniques for examining and manipulating cell surface oligosaccharides through genetic, enzymatic, and chemical strategies. ScTyrY43G and MmPheT413G label overlapping but distinct proteomes in human cell lines, with broader proteome coverage upon their coexpression. Chen, X., Wu, P., Rousseas, M., Okawa, D., Gartner, Z., Zettl, A., Bertozzi, C. R. DNA-barcode directed capture and electrochemical metabolic analysis of single mammalian cells on a microelectrode array. The kinetic constants of Stf0 were measured, and the catalytic mechanism of the sulfuryl group transfer reaction was investigated in initial rate kinetics and product inhibition experiments. We combined CRISPR-Cas9 knockout screens with RNAsequencing analysis to discover age-related genetic modifiers of microglial phagocytosis. Webauthor = "Burrows, {Cynthia J.} Incorporation of sialosides into LOS was assessed by matrix-assisted laser desorption and electrospray ionization mass spectrometry. PKMTs are likely to have many additional substrates in addition to histones, but relatively few nonhistone substrates have been characterized, and the substrate specificity for many PKMTs has yet to be defined. Remodeling the sialylation status of cancer cells affected the susceptibility to NK cell cytotoxicity via Siglec-7 engagement in a variety of tumor types. In conclusion, the new ADAP assay can reliably detect the three cardinal islet autoantibodies/antibodies in 1muL serum with high sensitivity. We frame central issues regarding determination of protein-level variation and PTMs, including some paradoxes present in the field today. In the IASP 2018 workshop, ADAP achieved the highest sensitivity of all assays tested at 95% specificity (AS95) rating for GAD and IA-2 autoantibodies and top-tier performance for insulin autoantibodies. One prevalent M. tb-specific sulfated metabolite, termed sulfolipid-1 (SL-1), has been correlated with virulence though its specific biological function is not known. To address this deficiency, chemists have developed technologies to perturb glycan biosynthesis, profile their presentation at the systems level, and perceive their spatial distribution. View details for Web of Science ID 000179817000032, View details for Web of Science ID 000178916000001. Shin, S., Comolli, L. R., Tscheliessnig, R., Wang, C., Ki Tae Nam, K. T., Hexemer, A., Siegerist, C. E., De Yoreo, J. J., Bertozzi, C. R. D-Amino Acid Chemical Reporters Reveal Peptidoglycan Dynamics of an Intracellular Pathogen. View details for DOI 10.1074/jbc.M510520200, View details for Web of Science ID 000235426200035. Using this new method, the glycome analysis of cell membranes isolated from human embryonic stem cells and somatic cell lines was performed. Mycobacterial carbohydrate sulfotransferase Stf0 catalyzes the sulfuryl group transfer from 3'-phosphoadenosine-5'-phosphosulfate (PAPS) to trehalose. N-butanoylmannosamine blocked polysialylation of NCAM and significantly reduced neurite outgrowth comparable with enzymatic removal of PSA by endoneuraminidases. In doing so, we examine prevailing notions about the number of modifications displayed on human proteins and how they combine to generate the protein diversity underlying health and disease. View details for DOI 10.1074/mcp.M111.010660, View details for Web of Science ID 000302786500006, View details for PubMedCentralID PMC3322563. 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. Mucin biopolymers and long-chain polysaccharides within the glycocalyx can generate entropic forces that favor or disfavor the projection of spherical and finger-like extensions from the cell surface. Structural and mechanistic studies of this family of sulfotransferases have been hindered by the lack of a productive recombinant protein expression system. 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. Onoe, H., Hsiao, S. C., Douglas, E. S., Gartner, Z. J., Bertozzi, C. R., Francis, M. B., Mathies, R. A. Sulfolipid-1 Biosynthesis Restricts Mycobacterium tuberculosis Growth in Human Macrophages. View details for Web of Science ID 000207584000003, View details for PubMedCentralID PMC138933. Our results demonstrate the potential of enzyme-activated probes for rapid pathogen discrimination for infectious diseases. We demonstrated the noninvasive imaging of glycans in live developing zebrafish, using a chemical reporter strategy. These anchor analogues were similar in length to native GPI anchors and included mimics of the native structure's three domains. It is hosted by the National Center for Biotechnology Information (NCBI) at the NCBI-Glycans Page (www.ncbi.nlm.nih.gov/glycans/snfg.html). The results address the mechanism by which sulfonucleotide reductases protect the covalent but labile enzyme-intermediate before release of sulfite by the protein cofactor thioredoxin. View details for Web of Science ID 000304129200013, View details for PubMedCentralID PMC3355658. View details for DOI 10.1002/anie.200806319, View details for Web of Science ID 000266415400022, View details for PubMedCentralID PMC2868584. Cotton Medal for Excellence in Chemical Research, This page was last edited on 1 March 2023, at 21:09. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. View details for Web of Science ID 000246816400009. Isotopic recoding is achieved via metabolic incorporation of a defined mixture of N-acetylglucosamine isotopologs into N-glycans. The remodeled cells were endowed with novel lectin binding profiles as determined by flow cytometry analysis. Sheta, R., Roux-Dalvai, F., Woo, C. M., Fournier, F., Bourassa, S., Bertozzi, C. R., Droit, A., Bachvarov, D. Glyco-seek: Ultrasensitive Detection of Protein-Specific Glycosylation by Proximity Ligation Polymerase Chain Reaction. View details for Web of Science ID 000173233300006, View details for PubMedCentralID PMC117506. This process involves two steps. Cell surfaces are endowed with biological functionality designed to mediate extracellular communication. These effects were mirrored by expression of the ectodomain of cancer-associated mucin MUC1. Webauthor = "Burrows, {Cynthia J.} We developed a baculovirus expression system for five of the seven cloned GSTs and determined their kinetic parameters using both thin-layer chromatography and a recently developed polymer dot-blot assay. Sulfurcontaining molecules were initially identified by mass spectral analysis of cell extracts from bacteria labeled metabolically with a stable sulfur isotope (34SO 4 2-). View details for Web of Science ID 000185051300005. In particular, she showed that such reactions could be carried out inside living cells to map molecules and cell function, without disturbing normal cellular chemistry. Bertozzi has applied the techniques of bioorthogonal chemistry to study glycocalyx, the sugars that surround the cell membrane. Under nondenaturing conditions, a distribution of the apoprotein, a 2Fe-2S intermediate, and the 4Fe-4S holoprotein were observed. [3] At Stanford University, she holds the Anne T. and Robert M. Bass Professorship in the School of Humanities and Sciences. View details for Web of Science ID 000257257100003, View details for PubMedCentralID PMC2663890. View details for Web of Science ID 000255629400034, View details for PubMedCentralID PMC2724873. Such metabolic interference can block the expression of oligosaccharides or alter the structures of the sugars presented on cells. [14][15] After graduating from Harvard in 1988, she worked at Bell Labs with Chris Chidsey. Such genetic engineering in combination with stable isotopic labeling can be applied to various metabolic pathways and their products. The antibodies recognized cells that were fed the unnatural biosynthetic precursor, and were capable of directing complement-mediated lysis.Structural alteration of sialic acids replaces a tolerized self-antigen with an antigenic determinant. [20][21], After graduating from Berkeley with a Ph.D., Bertozzi was a postdoctoral fellow at University of California, San Francisco (UCSF) with Steven Rosen, where she studied the activity of endothelial oligosaccharides in promoting cell adhesion at inflammation sites. A., Berger, J. M., Bertozzi, C. R. The roles of enzyme localisation and complex formation in glycan assembly within the Golgi apparatus, Functional self-assembling bolaamphiphilic polydiacetylenes as colorimetric sensor scaffolds, Trehalose is required for growth of Mycobacterium smegmatis. The ability to chemoselectively monitor H(2)O(2) fluxes in real time in living animals offers opportunities to dissect H(2)O(2)'s disparate contributions to health, aging, and disease. However, the complexities of glycan biosynthesis prevent the installation of nonnatural moieties at defined, predictable locations within glycoproteins at high levels of incorporation. A comparative study of bioorthogonal reactions with azides. Senaratne, R. H., De Silva, A. D., Williams, S. J., Mougous, J. D., Reader, J. R., Zhang, T. J., Chan, S., Sidders, B., Lee, D. H., Chan, J., Bertozzi, C. R., Riley, L. W. Mucin granule intraluminal organization in living mucous/goblet cells - Roles of protein post-translational modifications and secretion. She coined the term bioorthogonal chemistry to A., Boojamra, C. G., Griggs, J. L., Bertozzi, C. R. Tin-mediated phosphorylation: Synthesis and selectin binding of a phospho Lewis a analog. This approach can highlight changes in physiology or environment and may be more informative than steady-state analyses. Goon, S., Schilling, B., Tullius, M. V., Gibson, B. W., Bertozzi, C. R. GlcNAc 2-epimerase can serve a catabolic role in sialic acid metabolism. View details for DOI 10.1002/anie.201508861, View details for Web of Science ID 000368061800024, View details for PubMedCentralID PMC4715665. The enrichment method is based on covalent capture of azide-containing peptides by the azide-reactive cyclooctyne (ARCO) resin and is demonstrated for two different applications. Single-particle tracking was used to characterize the diffusion dynamics of injected quantum dots in the cytosol. Both the Staudinger ligation and the strain-promoted [3 + 2] cycloaddition using optimized cyclooctynes were effective for tagging azides on live cells. FGE has emerged as an enabling biotechnology tool due to the robust utility of the aldehyde product as a bioconjugation handle in recombinant proteins. The key building block was a 2-azido-3-thiogalactose-Thr analogue that was incorporated into a peptide by fluorenylmethoxycarbonyl (Fmoc)-based solid-phase peptide synthesis. Gas-phase stability of the 4Fe-4S cluster was investigated using both in-source and collision induced dissociation, which provided information regarding the relative gas-phase binding strength of iron towards protein ligands and inorganic sulfides. Through comparative analysis of screens with ADCs bearing different linkers, we show that a subset of late endolysosomal regulators selectively influence toxicity of noncleavable linker ADCs. 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. WebAbout Carolyn's Work. Hemmerich, S., Bertozzi, C. R., Leffler, H., ROSEN, S. D. FLUORESCENCE PROBES IN BIOCHEMISTRY - AN EXAMINATION OF THE NONFLUORESCENT BEHAVIOR OF DANSYLAMIDE BY PHOTOACOUSTIC CALORIMETRY. View details for DOI 10.1016/j.devcel.2019.04.035. T2S moiety of SL-1 Page ( www.ncbi.nlm.nih.gov/glycans/snfg.html ) dynamics of injected quantum dots in the School Humanities... 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