Synthetic Siglec-9 Agonists Inhibit Neutrophil Activation Associated with COVID-19. The location of the surface-anchored TS resulted too far off as to be capable to sialylate mucins, a role played by the shed TS instead. Microglia maintain homeostasis in the central nervous system through phagocytic clearance of protein aggregates and cellular debris. These uridine analogs represent the first generation of chemical tools to study the functions of mucin-type O-linked glycosylation. 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R. An inhibitor of O-glycosylation induces apoptosis in NIH3T3 cells and developing mouse embryonic mandibular tissues (Retracted Article. By contrast, most bacteria use trehalose solely as a general osmoprotectant or thermoprotectant. and Irmgard Chu Distinguished Professorship in Chemistry (2005); Havinga Medal, Univ. Dai, T. n., Xie, J. n., Zhu, Q. n., Kamariza, M. n., Jiang, K. n., Bertozzi, C. R., Rao, J. n. Optimal Dissociation Methods Differ for N- and O-glycopeptides. A sensitive electrospray ionization mass spectrometry-based assay was used to extract the kinetic parameters for PAP, revealing a K m (8.1 +/- 3.1 microM) and k cat (5.4 +/- 1.1 s (-1)) comparable to those reported for other CysQ enzymes. Varki, A., Cummings, R. D., Esko, J. D., Freeze, H. H., Stanley, P., Marth, J. D., Bertozzi, C. R., Hart, G. W., Etzler, M. E. Control of the Molecular Orientation of Membrane-Anchored Biomimetic Glycopolymers. Long term inhibition of mucin-type O-glycosylation, sialylation, or sulfation altered SHGFP-MUC5AC/CK characteristic diffusion time (t(1/2)), whereas all but sulfation diminished its mobile fraction. summa cum laude in chemistry from Harvard University, where she worked with Professor Joe Grabowski on the design and construction of a photoacoustic calorimeter. Hsiao, S. C., Crow, A. K., Lam, W. A., Bertozzi, C. R., Fletcher, D. A., Francis, M. B. To validate our results, we employed gel shift assays based on conjugating mass tags to O-GlcNAc groups. Cells adorned with longer glycopolymers showed increased metastatic potential, enhanced cell cycle progression, and greater levels of integrin-FAK mechanosignaling and Akt signaling in a syngeneic mouse model of metastasis. In this Account, we focus on research in our laboratory that seeks to transform the study of glycan function from a challenge to routine practice. However, currently available agonists are heterogeneous glycoconjugates and polysaccharides from natural sources. and Irmgard Chu Distinguished Professorship in Chemistry, 2007 LGBTQ Scientist of the Year Award from the, 2008 Li Ka Shing Women in Science Award, 2008 Roy L. Whistler International Award in Carbohydrate Chemistry, 2009 Albert Hofmann Medal, Univ. On this Wikipedia the language links are at the top of the page across from the article title. Carolyn R. Bertozzi, in full Carolyn Ruth Bertozzi, (born October 10, 1966, Boston, Massachusetts), American chemist known for her application of chemical synthesis to the study of biological systems. She coined the term bioorthogonal chemistry to describe the use of click reactionsquick, simple chemical reactions to study living cells. We identified a concise disaccharide motif, GlcNAc beta 1-->6Gal alpha-R, that preserved both recognition and specificity determinants for the GlcNAc-6-0-sulfotransferase. Dibenzoselenacycloheptynes were prepared in three steps from commercially available reagents and trapped in situ with benzyl azide to form the corresponding triazoles. The simplicity and generality of this method make it well suited for use in the study of carbohydrate-mediated cell surface interactions. Biochemical studies demonstrated that the enzyme requires unmodified trehalose as substrate and is sensitive to small structural perturbations of the disaccharide. View details for DOI 10.1038/s41586-019-1088-4, View details for Web of Science ID 000464412700039, View details for DOI 10.1073/pnas.1813020116, View details for Web of Science ID 000463936900024. Applying IsoStamp, we were able to detect femtomole quantities of a single tagged protein from total mammalian cell lysates at signal-to-noise ratios as low as 2.5:1. Applications to the visualization of cellular glycans and enrichment of glycoproteins for proteomic analysis are described. [27][44], She co-founded Grace Science Foundation in 2018. We then demonstrated that in these microarrays, the glycopolymer ligands bind lectins according to the structures of their pendant glycans. To evaluate differential glycosylation in EOC caused by modulations in GALNT3 expression, we used a metabolic labeling strategy for enrichment and mass spectrometry-based characterization of glycoproteins following GALNT3 gene knockdown (KD) in A2780s EOC cells. Here we report the development of an HIV OF assay based on Antibody Detection by Agglutination-PCR (ADAP) technology. 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. In this study, we performed a proteomic analysis of the membrane fraction from latex bead-containing (LBC) phagosomes isolated from macrophages. Most progress has occurred in the area N-glycoproteomics. Mycobacteria, including the pathogen Mycobacterium tuberculosis, use the non-mammalian disaccharide trehalose as a precursor for essential cell-wall glycolipids and other metabolites. Lastly, we show that sialic acid depletion enhances ADC lysosomal delivery and killing in diverse cancer cell types, including with FDA (US Food and Drug Administration)-approved trastuzumab emtansine (T-DM1) in Her2-positive breast cancer cells. View details for DOI 10.1021/jacs.5b02383, View details for Web of Science ID 000356322300038, View details for PubMedCentralID PMC4487548. Disruption of papA2 and papA1 in M. tuberculosis confirmed their essential role in SL-1 biosynthesis and their order of action. She also later developed a click reaction called the strain-promoted alkyne-azide cycloaddition, which, unlike other click reactions involving azides and alkynes, did not require toxic copper ions for the azide to snap together with the alkyne and was highly effective for tracking glycans in live cells. View details for DOI 10.1099/jmm.0.46983-0, View details for Web of Science ID 000245795600002. There is urgent need for new therapeutic targets and a better understanding of EOC initiation and progression. View details for Web of Science ID 000310103800025, View details for PubMedCentralID PMC3596100. The azido sugars are then covalently tagged with imaging probes or epitope tags, either ex vivo or in vivo, using an azide-specific reaction. This may be a result of BPA sulfation/desulfation providing a pathway for selective uptake into hormone-responsive cells. Her research group profiles changes in cell surface glycosylation associated with cancer, inflammation and bacterial infection, and uses this information to develop new View details for Web of Science ID 000267694600045, View details for PubMedCentralID PMC2761887. Lantos, A. This protocol outlines both the generation and the analysis of proteins aldehyde-tagged at their termini and the methods for chemical conjugation to the formylglycine. 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. Zhou, X., Rodriguez-Rivera, F. P., Lim, H., Bell, J. C., Bernhardt, T. G., Bertozzi, C. R., Theriot, J. These studies are currently in progress in our laboratory. We report the synthesis of an alpha-formylglycine building block suitable for Fmoc-based solid-phase peptide synthesis. View details for DOI 10.1074/jbc.M212127200, View details for Web of Science ID 000181466800038, View details for Web of Science ID 000181517000014. View details for DOI 10.1073/pnas.1213186110, View details for Web of Science ID 000313630300024. Symbol Nomenclature for Graphical Representations of Glycans. Biological analysis of diptericin fragments indicated that the main determinant of antibacterial activity lay in the C-terminal region that is similar to the attacin peptides, although the N-terminal segment, related to the proline-rich family of antibacterial peptides, augmented that activity by 100-fold. View details for Web of Science ID 000279196500017, View details for PubMedCentralID PMC2890245. Dr. Carolyn R. Bertozzi Ph.D. serves as Independent Director of the Company. A., Quang, C. N., Bertozzi, C. R. A sulfated metabolite produced by stf3 negatively regulates the virulence of Mycobacterium tuberculosis. View details for DOI 10.1111/j.1365-2958.2006.05075.x, View details for Web of Science ID 000235842600009. View details for Web of Science ID 000423267000106, View details for Web of Science ID 000423267000140, View details for DOI 10.1021/acscentsci.7b00540, View details for PubMedCentralID PMC5704282, View details for PubMedCentralID PMC5658776, View details for Web of Science ID 000412089800691, View details for Web of Science ID 000429556701925, View details for Web of Science ID 000429556703083, View details for Web of Science ID 000429556702657, View details for Web of Science ID 000429556702049. Biochemistry in the context of a living cell or organism is complicated by many variables such as supramolecular organization, cytoplasmic viscosity, and substrate heterogeneity. A. Glycans in cancer and inflammation. Application of the IsoTaG platform to 15 cell lines metabolically labeled with Ac4GalNAz or Ac4ManNAz revealed 1375 N- and 2159 O-glycopeptides, variously modified with 74 discrete glycan structures. After nearly two decades as a professor at UC Berkeley, she uprooted her lab in 2015 in search of resources at Stanfordincluding an on-campus hospital and the schools entrepreneurial culturethat would better enable her to bring her academic work into the real world. 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. Thus, a bulky glycocalyx is a feature of tumour cells that could foster metastasis by mechanically enhancing cell-surface receptor function. This observation stood in stark contrast to the slow kinetics associated with 1,3-dipolar cycloaddition of azides with unstrained, linear alkynes, the conventional Huisgen process. In the paper, Dr. Bertozzi and her team described a new method of engineering an antibody to shuttle a targeted extracellular When evaluating mouse thymocytes and splenocytes as acceptors of the azido-sugar, a complex pattern of efficiently tagged glycoproteins was revealed. 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. View details for DOI 10.1074/jbc.M109.017236, View details for Web of Science ID 000268097400064, View details for PubMedCentralID PMC2740463. These screens identified CD22, a canonical Bcell receptor, as a negative regulator of phagocytosis that is upregulated on aged microglia. This protocol details the syntheses of the azido sugars N-azidoacetylmannosamine (ManNAz), N-azidoacetylgalactosamine (GalNAz), N-azidoacetylglucosamine (GlcNAz) and 6-azidofucose (6AzFuc), and the detection reagents phosphine-FLAG and phosphine-FLAG-His6. This review summarizes current efforts to obtain homogeneous glycopeptide and glycoprotein materials by a variety of methods that draw from the techniques of recombinant expression, chemical synthesis, enzymatic transformation, and chemoselective ligation. Parak, W. J., Gerion, D., Zanchet, D., Woerz, A. S., Pellegrino, T., Micheel, C., Williams, S. C., Seitz, M., Bruehl, R. E., Bryant, Z., Bustamante, C., Bertozzi, C. R., Alivisatos, A. P. Stereloselective synthesis of myo-inositol via ring-closing metathesis: A building block for glycosylphosphatidylinositol (GPI) anchor synthesis. View details for DOI 10.1021/jacs.6b12541, View details for PubMedCentralID PMC5345120. Since azides can be metabolically incorporated into cellular proteins and oligosaccharides, this dye may be a useful tool for profiling proteins and their posttranslational modifications. Metabolic incorporation of d-alanine derivatives and click chemistry detection constitute a facile, modular platform that facilitates unprecedented spatial and temporal resolution of PG dynamics in vivo. Cardiac myoblasts were also captured. The unique chemical functionality of these analogs is exploited for selective attachment of singlet oxygen-generating fluorescent dyes via bioorthogonal 'click chemistry' ligations. Methods capable of directing orientation, as well as an understanding of the underlying physical mechanisms are, however, lacking. Malaker, S. A., Pedram, K., Ferracane, M. J., Bensing, B. Bowman, K. G., Cook, B. N., de Graffenried, C. L., Bertozzi, C. R. The evolving academic research environment, Chemical synthesis of lymphotactin: A glycosylated chemokine with a C-terminal mucin-like domain. View details for DOI 10.1016/j.chembiol.2004.05.009, View details for Web of Science ID 000222987300018, View details for DOI 10.1002/cbic.200300789, View details for Web of Science ID 000220196800018. 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. However, the synthetic difficulties inherent to sialylated and fucosylated oligosaccharides motivate the search for alternative antagonists. View details for DOI 10.1371/journal.pone.0242049. Born: 10 October 1966, Boston, MA, USA. WebAbout our Founding. Tuberculosis (TB) is the leading cause of death from an infectious bacterial disease. The ESI-MS assay is used to determine NodST kinetic parameters, including K(M), V(max), and K(i) (for PAP). Additionally, we have utilized computational methods to understand the unique properties of these fully conjugated macrocycles. A step in this direction will be the development of tools to identify metabolites that share common structural features. A comparative study of bioorthogonal reactions with azides. One method to achieve this involves the utilization of a non-natural amino acid by the cell's native translational apparatus. Bertozzi is a member of the Royal Society and the academies of sciences of Germany and the United States. Membrane-proximal N-linked glycosylation was critical for maintaining the ligand dependence of the receptor. View details for DOI 10.1073/pnas.0900717106, View details for Web of Science ID 000264522600009, View details for PubMedCentralID PMC2660766. The results were in excellent agreement with those obtained from previous assays, verifying the accuracy and reliability of the ESI-MS assay. Recently it was shown that the mucin GlyCAM-1, a secreted physiological ligand for L-selectin, is capped with sulfated derivatives of sialyl Lewis x [sLe(x): Sia alpha 2-->3Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc] and that sulfation is required for the high-affinity interaction between GlyCAM-1 and L-selectin. Here, we report the development of a nanoscale cell injection system (termed the nanoinjector) that uses carbon nanotubes to deliver cargo into cells. We tested this prediction by investigating whether bulky glycoproteins in the glycocalyx promote a tumour phenotype in human cells by increasing integrin adhesion and signalling. Cell surface carbohydrates mediate interactions between the cell and its environment. Bertozzi holds the Anne T. and Robert M. Bass Professorship in the School of Humanities and Sciences at Stanford University. Assignment of intact glycan structures to specific protein attachment sites is a critical step towards elucidating the function encoded in the glycome. View details for Web of Science ID 000262171100029, View details for PubMedCentralID PMC2655317. View details for Web of Science ID 000266929900058, View details for PubMedCentralID PMC2812030, View details for Web of Science ID 000265985200026. Baker Family Director of Stanford ChEM-H, Anne T. and Robert M. Bass Professor in the School of Humanities and Sciences and Professor, by courtesy, of Chemical and Systems Biology and of Radiology, AB, Harvard University, Chemistry (1988). View details for Web of Science ID 000291896400004, View details for PubMedCentralID PMC3117394. We also combined LplA labeling with our previous biotin ligase labeling, to simultaneously image the dynamics of two different receptors, coexpressed in the same cell. Given that M. tuberculosis typically persists in the phagosomal vacuole after being phagocytosed by macrophages, we performed a proteomic analysis of that organelle after treatment of macrophages with LAMs purified from the two mycobacterial species. The omega-alkynyl-myristate and -palmitate analogs used with click chemistry and azido-probes will be invaluable to study protein acylation in vitro, in cells, and in vivo. WebBio. In this work, we apply an aluminum "lift off" lithography method to allow the efficient generation of complex patterns comprising different DNA sequences. Walton, E. M., Cronan, M. R., Cambier, C. J., Rossi, A., Marass, M., Foglia, M. D., Brewer, W., Poss, K. D., Stainier, D. R., Bertozzi, C. R., Tobin, D. M. A tension-mediated glycocalyx-integrin feedback loop promotes mesenchymal-like glioblastoma. View details for DOI 10.1016/j.cell.2015.11.048, View details for PubMedCentralID PMC4715264. Lim, H. C., Sher, J. W., Rodriguez-Rivera, F. P., Fumeaux, C. n., Bertozzi, C. R., Bernhardt, T. G. The mucin-selective protease StcE enables molecular and functional analysis of human cancer-associated mucins. 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. A., Bertozzi, C. R. Investigation of the iron-sulfur cluster in Mycobacterium tuberculosis APS reductase: Implications for substrate binding and catalysis. Methods for site-specific protein conjugation are critical to such efforts. A significant proportion (>45%) of the identified O-GlcNAc sites lie in close proximity to or coincide with a known phosphorylation site, supporting the potential for PTM crosstalk. Bertozzi, C. R., Chang, C. J., Davis, B. G., Olvera de la Cruz, M., Tirrell, D. A., Zhao, D. Integrins Form an Expanding Diffusional Barrier that Coordinates Phagocytosis. At elevated temperatures, however, the mutant was unable to proliferate even in the presence of trehalose. Yang, A. C., Stevens, M. Y., Chen, M. B., Lee, D. P., Stahli, D., Gate, D., Contrepois, K., Chen, W., Iram, T., Zhang, L., Vest, R. T., Chaney, A., Lehallier, B., Olsson, N., du Bois, H., Hsieh, R., Cropper, H. C., Berdnik, D., Li, L., Wang, E. Y., Traber, G. M., Bertozzi, C. R., Luo, J., Snyder, M. P., Elias, J. E., Quake, S. R., James, M. L., Wyss-Coray, T. Membrane-tethered mucin-like polypeptides sterically inhibit binding and slow fusion kinetics of influenza A virus. Bertozzi remains a part of the advisory board for the biologics sector of the company. IsoTaG is therefore an effective platform for identification of intact glycopeptides labeled by alkynyl or azido sugars and will facilitate further studies of the glycoproteome. Appel, M. J., Meier, K. K., Lafrance-Vanasse, J., Lim, H., Tsai, C., Hedman, B., Hodgson, K. O., Tainer, J. View details for Web of Science ID 000177054900001, View details for Web of Science ID 000175790100030, Here we report a concise stereoselective synthesis of myo-inositol via ring-closing metathesis. Their dense glycosylation is believed to confer structural rigidity as well as molecular extension beyond the glycocalyx, crucial to interaction with the cellular environment. View details for DOI 10.1016/j.devcel.2019.04.035. We further generated rapamycin-inducible chimeric enzymes comprising the localization domain of a sulfotransferase and the catalytic domain of a glycosyltransferase, demonstrating the generality of the system among other Golgi enzymes. Wojczyk, B. S., Stwora-Wojczyk, M. M., Hagen, F. K., Striepen, B., Hang, H. C., Bertozzi, C. R., Roos, D. S., Spitalnik, S. L. Metabolic oligosaccharide engineering as a tool for glycobiology, Formation of 1,1-alpha,alpha-glycosidic bonds by intramolecular aglycone delivery. We used the method to directly assay the O-GlcNAcylation status of a low-abundance transcription factor from cell lysates without need for isolation or enrichment. We have therefore made use of recently developed synthetic mucin mimetics, in which the core alpha-GalNAc monosaccharides of natural mucins are conjugated to a lipidated polymer backbone and anchored to fluid, solid-supported lipid membranes, and fluorescence interference contrast microscopy, an optical technique that provides nanometer-scale topographic information about objects near a reflective interface, to measure the orientation of the mucin mimics relative to the membrane plane. A critical branch point in mucin-type oligosaccharides is the beta 1-->3 glycosidic linkage to the core alpha-N-acetylgalactosamine (GalNAc) residue. View details for DOI 10.1016/j.celrep.2013.08.048, View details for Web of Science ID 000328263000025, View details for PubMedCentralID PMC3869705, View details for DOI 10.1371/journal.pone.0072304, View details for Web of Science ID 000323425700163. We report herein the chemical synthesis and preliminary mechanistic investigation of diptericin, an 82 residue glycopeptide that contains regions similar to two different types of antibacterial peptides. Sulfite is then released in a thioredoxin-dependent manner. The unnatural sialic acid analog, N-levulinoyl sialic acid (SiaLev), was incorporated into cell surface glycoconjugates including PSA by the incubation of cultured neurons with the metabolic precursor N-levulinoylmannosamine (ManLev). Using these probes, chemoselective imaging of either H(2)O(2) or caspase 8 activity was performed in vitro and in vivo. Mycobacterium tuberculosis synthesizes specific polyketide lipids that interact with the host and are required for virulence. These results show that CysH is important for Mtb protection during the chronic infection phase, and that resistance to nitrosative and oxidative stress may be the mechanism of this protection. of Chemistry (2018); Foreign Member of the Royal Society Inductee (2018); National Inventors Hall of Fame Inductee (2017); Arthur C. Cope Award (2017); UCSF 150th Anniversary Alumni Excellence Award (2015); Hans Bloemendal Award (Radboud Univ. Shin, Y., Winans, K. A., Backes, B. J., KENT, S. B., Ellman, J. Here we explored their effect on corneal surface glycosylation using a metabolic label, tetra-acetylated N-azidoacetylgalactosamine (Ac4GalNAz). We show that Glyco-seek detects attomoles of glycoproteins of interest from cell lysates, with sensitivity several orders of magnitude higher than that of current techniques. Now N-(4-pentynoyl)mannosamine can be used to metabolically label sialylated glycoproteins in living animals, enabling future identification of new biomarkers. Cioce, A., Bineva-Todd, G., Agbay, A. J., Choi, J., Wood, T. M., Debets, M. F., Browne, W. M., Douglas, H. L., Roustan, C., Tastan, O. Y., Kjaer, S., Bush, J. T., Bertozzi, C. R., Schumann, B. LYTACs that engage the asialoglycoprotein receptor for targeted protein degradation. 56Carolyn Bertozzi 12 Bertozzi won the prize for studying the sugar coats of cells. We identified fluorescein-trehalose analogues that are metabolically incorporated into the trehalose mycolates of representative Mycobacterium, Corynebacterium, Nocardia, and Rhodococcus species. Carolyn R. Bertozzi, in full Carolyn Ruth Bertozzi, (born October 10, 1966, Boston, Massachusetts), American chemist known for her application of chemical synthesis to the study of biological systems. In some cases, the functional significance of disease-associated changes in glycosylation has been revealed. This tutorial review focuses on recent applications of homogeneous synthetic glycopeptides and glycoproteins for studies of structure and function. We used this method to identify interaction partners for the O-GlcNAc-modified FG-repeat nucleoporins. Specifically, three carbohydrate binding proteins termed selectins (E-, P-, and L-selectin) have been shown to be essential for leukocyte rolling along the vascular endothelium, the first step in the recruitment of leukocytes from the blood into inflammatory sites or into secondary lymphoid organs. Some awards of note include the Lemelson-MIT award for inventors, Whistler Award, Ernst Schering Prize, MacArthur Foundation Fellowship, the ACS Award in Pure Chemistry, Tetrahedron Young Investigator Award, and Irving Sigal Young Investigator Award of the Protein Society. Drake, P. M., Stock, C. M., Nathan, J. K., Gip, P., Golden, K. P., Weinhold, B., Gerardy-Schahn, R., Bertozzi, C. R. Selective Enrichment of Azide-Containing Peptides from Complex Mixtures. Chang, P. V., Prescher, J. The end purpose of the described approaches is the production of glycosylated materials for experiments relevant to the biological investigation of glycoproteins, although the strategies presented apply to other posttranslational modifications as well. Thus, a canonical Bcell receptor, as well as an understanding of EOC and! On aged microglia born: 10 October 1966, Boston, MA USA! To validate our results, we employed gel carolyn bertozzi biography assays based on Antibody Detection by Agglutination-PCR ADAP., View details for Web of Science ID 000265985200026 protein attachment sites is a critical step elucidating! Been revealed > 3 glycosidic linkage to the core alpha-N-acetylgalactosamine ( GalNAc ) residue PubMedCentralID PMC4487548 generality! Pubmedcentralid PMC4487548 B., Ellman, J heterogeneous glycoconjugates and polysaccharides from natural sources Mycobacterium,,!, C. 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