In addition, the general assay architecture should be readily applicable to high-throughput screens of other carbohydrate sulfotransferases. Mucin-domain glycoproteins are known to be key players in a host of human diseases, especially cancer, wherein mucin expression and glycosylation patterns are altered. Dehnert, K. W., Beahm, B. J., Huynh, T. T., Baskin, J. M., Laughlin, S. T., Wang, W., Wu, P., Amacher, S. L., Bertozzi, C. R. Metabolic cross-talk allows labeling of O-linked beta-N-acetylglucosamine-modified proteins via the N-acetylgalactosamine salvage pathway. Methods for site-specific protein conjugation are critical to such efforts. Furthermore, we show that these mimetics enhance the survival of nonmalignant cells in a zebrafish model of metastasis. A mineralization technique was developed that exposes carboxylate groups on the surface of cross-linked pHEMA, promoting high-affinity nucleation and growth of calcium phosphate on the surface, along with extensive calcification of the hydrogel interior. View details for DOI 10.1016/j.chembiol.2015.07.009, View details for PubMedCentralID PMC4567249, View details for DOI 10.1021/acscentsci.5b00245, View details for PubMedCentralID PMC4827477. Research into protein glycosylation, therefore, has benefited from homogeneous, structurally-defined glycoproteins obtained by chemical synthesis. In contrast, polySia expression and function in the nervous system has been well characterized. Unbound particles randomize direction by Brownian rotation too quickly to be detected. Although genetically encoded tags such as GFP are widely used to monitor discrete proteins, they can cause significant perturbations to a protein's structure and have no direct extension to other classes of biomolecules such as glycans, lipids, nucleic acids and secondary metabolites. Finally, we obtained structural and computational data that revealed the relationship between the conformation of BARAC's central lactam and compound reactivity. Sulfite is then released in a thioredoxin-dependent manner. Recently, the ability to modify monosaccharide structures within cellular glycans through metabolic processes has offered a new avenue for biological studies. NodST catalyzes the sulfuryl group transfer from 3'-phosphoadenosine 5'-phosphosulfate (PAPS) to chitobiose, generating 3'-phosphoadenosine 5'-phosphate (PAP) and chitobiose-6-OSO(3)(-) as products. New developments have allowed researchers to begin probing the inner workings of the cell to gain new insight into cell function and metabolism. View details for Web of Science ID 000240465200023, View details for PubMedCentralID PMC3233198. Seeliger, J. C., Topp, S., Sogi, K. M., Previti, M. L., Gallivan, J. P., Bertozzi, C. R. Thiacycloalkynes for Copper-Free Click Chemistry. View details for Web of Science ID 000478861203266, View details for Web of Science ID 000478860500774, View details for Web of Science ID 000478860501585, View details for DOI 10.1073/pnas.1818274116, View details for Web of Science ID 000461679000031. 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. View details for Web of Science ID 000263320900008, View details for PubMedCentralID PMC2709987. Tomlin, F. M., Gerling-Driessen, U. I., Liu, Y. C., Flynn, R. A., Vangala, J. R., Lentz, C. S., Clauder-Muenster, S. n., Jakob, P. n., Mueller, W. F., Ordoez-Rueda, D. n., Paulsen, M. n., Matsui, N. n., Foley, D. n., Rafalko, A. n., Suzuki, T. n., Bogyo, M. n., Steinmetz, L. M., Radhakrishnan, S. K., Bertozzi, C. R. Ingredients for a Positive Safety Culture. Ni bis(dithiolene) probes selectively labeled quadricyclane-modified bovine serum albumin, even in the presence of cell lysate. This assay design shows excellent performance in 384-well format and is sensitive to known, non-specific palmitoylation inhibitors. A., Ogorzalek Loo, R. R., Lundberg, E. n., MacCoss, M. J., Mallick, P. n., Mootha, V. K., Mrksich, M. n., Muir, T. W., Patrie, S. M., Pesavento, J. J., Pitteri, S. J., Rodriguez, H. n., Saghatelian, A. n., Sandoval, W. n., Schlter, H. n., Sechi, S. n., Slavoff, S. A., Smith, L. M., Snyder, M. P., Thomas, P. M., Uhln, M. n., Van Eyk, J. E., Vidal, M. n., Walt, D. R., White, F. M., Williams, E. R., Wohlschlager, T. n., Wysocki, V. H., Yates, N. A., Young, N. L., Zhang, B. n. Mapping and quantification of over 2,000 O-linked glycopeptides in activated human T cells with isotope-targeted glycoproteomics (IsoTaG). Here, we systematically explore the advantages and disadvantages of conventional HCD, sceHCD, ETD, and EThcD for intact glycopeptide analysis and determine their suitability for both N- and O-glycoproteomic applications. Here, we engineer living cells to tag glycans with editable chemical functionalities while providing information on biosynthesis, physiological context, and glycan fine structure. Breidenbach, M. A., Gallagher, J. E., King, D. S., Smart, B. P., Wu, P., Bertozzi, C. R. Copper-free click chemistry in living animals. View details for Web of Science ID 000077466300003, View details for Web of Science ID 000077383600001. View details for Web of Science ID 000232605600062. Mild hydrolysis conditions were established that released sulfated oligosaccharides without cleavage of sulfate esters. Many unique lipids and glycolipids from the Mtb cell wall are thought to be virulence factors that mediate host-pathogen interactions. We present IsoTaG, a mass-independent chemical glycoproteomics platform for characterization of intact, metabolically labeled glycopeptides at the whole-proteome scale. Our results show that, like palmitate, incorporation of azido-palmitate occurred on mitochondrial proteins via thioester bonds at sites that could be competed out by palmitoyl-CoA. Nonetheless, the glycosylation on cell membranes remains not well characterized because of the lack of sensitive analytical methods. These receptors have attracted great attention in recent years due to their participation in a number of acute and chronic inflammatory diseases. She is a member of the National Academy of Sciences (2005), the Institute of Medicine (2011), and the National Academy of Inventors (2013). A chemical approach to unraveling the biological function of the glycosylphosphatidylinositol anchor. View details for Web of Science ID A1994PH46500004. A., Bertozzi, C. R. Investigation of the iron-sulfur cluster in Mycobacterium tuberculosis APS reductase: Implications for substrate binding and catalysis. The resulting surfaces are then demonstrated to be able to capture up to three distinct types of living cells in specific locations. View details for Web of Science ID 000222612600032. Bertozzis graduate research focused on carbohydrate analog synthesis, intended for biological applications. View details for Web of Science ID 000260193100005, View details for PubMedCentralID PMC2680727. In June 2015, she joined the faculty at Stanford University as an Institute Scholar at Sarafan ChEM-H. Prof. Bertozzi's research interests span the disciplines of chemistry and biology with an emphasis on studies of cell surface glycosylation pertinent to disease states. Oligosaccharides play a crucial role in many of the recognition, signaling, and adhesion events that take place at the surface of cells. One such development is creating chemical tools for studying glycans in living systems. Bertozzi, C. R., Fukuda, S., ROSEN, S. D. CRACKING THE CARBOHYDRATE CODE FOR SELECTIN RECOGNITION, IDENTIFICATION OF THE SULFATED MONOSACCHARIDES OF GLYCAM-1, AN ENDOTHELIAL-DERIVED LIGAND FOR L-SELECTIN. Although the mechanisms of Golgi enzyme localisation are still under debate, the distribution of these enzymes among the Golgi cisternae can dictate the overall structures produced by the cell. Stanford, CA 94305Phone: (650) 723-2501Campus Map, UndergraduatesPh.D. Thus the transient state exhibits the characteristics of a kinetic trap in a folding funnel. Incorporation studies using N-acylmannosamine analogues, N-glycolylneuraminic acid, and C-13-labeled N-acetylneuraminic acid. Myristoylation is the attachment of the 14-carbon fatty acid myristate to the N-terminal glycine residue of proteins. This phenotype probably reflects a decreased capacity of the ST8Sia IV(-/-) progenitors to escape from the bone marrow niche. By mutating catalytic residues of two such enzymes, we engineered mucin-selective binding agents with retained glycoform preferences. Polydiacetylene-based systems are attractive for sensing applications due to their colorimetric response to changes in the local environment. The biosynthesis of these glycoproteins is initiated by a family of polypeptide N-acetyl-alpha-galactosaminyltransferases (ppGalNAcTs) that modify proteins in the secretory pathway. Lin, F. L., van Halbeek, H., Bertozzi, C. R. Synthetic analogues of glycosylphosphatidylinositol-anchored proteins and their behavior in supported lipid bilayers. FGE has emerged as an enabling biotechnology tool due to the robust utility of the aldehyde product as a bioconjugation handle in recombinant proteins. Here, we extend LplA-based labeling to green- and red-emitting fluorophores by employing a two-step targeting scheme. Here, we report the development of antibody-sialidase conjugates that enhance tumor cell susceptibility to antibody-dependent cell-mediated cytotoxicity (ADCC) by selective desialylation of the tumor cell glycocalyx. Several changes have been made to the SNFG page in the past year to update the rules for depicting glycans using the SNFG, to include more examples of use, particularly for non-mammalian organisms, and to provide guidelines for the depiction of ambiguous glycan structures. Complete assignment of all (1)H and (13)C resonances in the spectra of these deoxytrehaloses was achieved through the extensive use of 2D [(1)H,(1)H] and [(1)H,(13)C] correlation NMR experiments. In this study, we examine the nature of the sulfate-modified carbohydrates of GlyCAM-1. To this end, we generated the first high-density library of transposon insertion mutants in the model organism C. glutamicum. Cell surface sialosides constitute a central axis of immune modulation that is exploited by tumors to evade both innate and adaptive immune destruction. The GPI anchor is a complex structure comprising a phosphoethanolamine linker, glycan core, and phospholipid tail. Most identified proteins were involved in mechanisms of cellular metabolic functions, post-translational modifications, and some have been reported to be implicated in EOC etiology. Through rational design, we redirected a microbial lipoic acid ligase (LplA) to specifically attach an alkyl azide onto an engineered LplA acceptor peptide (LAP). N-Acetylmannosamine (ManNAc) is the first committed intermediate in the sialic acid biosynthetic pathway; thus, the mechanisms that control intracellular ManNAc levels are important regulators of sialic acid production. We also exploited this finding to protect allogeneic and xenogeneic primary cells from NK-mediated killing, suggesting the potential of Siglecs as therapeutic targets in cell transplant therapy. 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. Wei, W., Riley, N. M., Yang, A. C., Kim, J. T., Terrell, S. M., Li, V. L., Garcia-Contreras, M., Bertozzi, C. R., Long, J. Together, localisation and association govern the assembly of complex glycans and thereby regulate interactions at the cell surface. In one step, 35S-labeled by-products are then eluted from the membrane, leaving spatially separated 35S-labeled product "dots" for subsequent quantification. Glycan structural diversity is directly correlated with difficulty in characterizing the intact glycoproteome by mass spectrometry (MS). Perez-Vilar, J., Mabolo, R., McVaugh, C. T., Bertozzi, C. R., Boucher, R. C. Molecular basis for G protein control of the prokaryotic ATP sulfurylase. Shes been out since the late 1980s, when being a lesbian could have jeopardized her career. Yao, J. Highly reactive cyclooctynes have been sought as substrates for Cu-free cycloaddition reactions with azides in biological systems. Subsequent bioorthogonal ligation with alkyne-functionalized probes enabled detection and visualization of cell-surface glycolipids. Pratt, M. R., Hang, H. C., Ten Hagen, K. G., Rarick, J., Gerken, T. A., Tabak, L. A., Bertozzi, C. R. Expanding the diversity of unnatural cell-surface sialic acids. 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. [88] Her father was a physics professor at the Massachusetts Institute of Technology. Chemical or genetic disruption of NGLY1 activity results in the accumulation of misprocessed Nrf1 that is largely excluded from the nucleus. Dr. 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. During postdoctoral work at UC San Francisco, she studied the activity of endothelial oligosaccharides in promoting cell adhesion at sites of inflammation. The loss of SL-1 (and SL(1278)) did not appear to affect bacterial replication or trafficking, suggesting that the functions of SL-1 are specific to human infection. A wide variety of bacterial species incorporated azide and alkyne-functionalized d-alanine into their cell walls, which we visualized by covalent reaction with click chemistry probes. Marschallinger, J., Iram, T., Zardeneta, M., Lee, S. E., Lehallier, B., Haney, M. S., Pluvinage, J. V., Mathur, V., Hahn, O., Morgens, D. W., Kim, J., Tevini, J., Felder, T. K., Wolinski, H., Bertozzi, C. R., Bassik, M. C., Aigner, L., Wyss-Coray, T. Lipid-droplet-accumulating microglia represent a dysfunctional and proinflammatory state in the aging brain. In this study we probed the importance of the stem region with respect to substrate preference, localization, and oligomerization. WebCarolyn Ruth Bertozzi (born October 10, 1966) is an American chemist and Nobel laureate, known for her wide-ranging work spanning both chemistry and biology. View details for DOI 10.1371/journal.pgen.1008284. The correlation of its abundance with the virulence of clinical isolates suggests a role for SL-I in pathogenesis, although its biological functions remain unknown. Additionally, we demonstrate that in C. glutamicum, the peripheral peptidoglycan layer at the septal junction remains contiguous throughout septation, forming a diffusion barrier for the fluid mycomembrane. Bioorthogonal reactions are chemical reactions that neither interact with nor interfere with a biological system. Furthermore, DMN-Tre labeling was reduced by treatment with TB drugs, unlike the clinically used auramine stain. 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. View details for Web of Science ID 000090003800038. These modified proteins integrated into the plasma membranes of a variety of mammalian cells and were internalized and directed to recycling endosomes similarly to GFP bearing a native GPI anchor. We further show that proteins containing azidohomoalanine can be selectively modified in the presence of other cellular proteins by means of Staudinger ligation with triarylphosphine reagents. 275, 21075-21080). Our methodology should provide general access to biochemical and imaging studies of cell surface proteins, using small fluorophores introduced via a short peptide tag. Low molecular weight and singly charged fragments, obtained by a combination of gel filtration and anion-exchange chromatography, were analyzed. Consistent with this view, increased levels of MMCoA led to increased abundance and mass of both PDIM and SL-1. The synthesis of a 93-residue chemokine, lymphotactin, containing eight sites of O-linked glycosylation, was achieved using the technique of native chemical ligation. View details for DOI 10.1016/j.bmcl.2007.05.008, View details for Web of Science ID 000248074600008, View details for PubMedCentralID PMC3225185, View details for Web of Science ID 000247759400001, View details for PubMedCentralID PMC2535820. 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. View details for DOI 10.1093/glycob/cwz045, View details for Web of Science ID 000493194700001. Thus, choice of enrichment strategy has profound implications on experimental outcomes. View details for Web of Science ID A1997WZ22500048. This system enables the production of glycoproteins that are functionalized for specific chemical modifications at their glycosylation sites. In cells, GlcNAc6ST-1 exists as a dimer; two cysteine residues within the stem and transmembrane domain were found to be critical for dimerization. Jacobs, C. L., Yarema, K. J., Mahal, L. K., Nauman, D. A., Charters, N. W., Bertozzi, C. R. Fmoc-based synthesis of peptide-(alpha)thioesters: Application to the total chemical synthesis of a glycoprotein by native chemical ligation. 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. The biological study of O-linked glycosylation is particularly problematic, as chemical tools to control this modification are lacking. ( Bertozzi A., Mills, J. R., Roforth, M. M., Pittock, S. J., McKeon, A., Page, K., Wolf, W. A., Sanda, S., Speake, C., Greenbaum, C. J., Tsai, C. Bump-and-Hole Engineering Identifies Specific Substrates of Glycosyltransferases in Living Cells. We provide genetic and biochemical evidence for the activities of two proteins, Chp1 and Sap (corresponding to gene loci rv3822 and rv3821), that complete this pathway. 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. [22][26] She has been an investigator with HHMI since 2000. WebDr. Our editors will review what youve submitted and determine whether to revise the article. Structural and mechanistic studies of this family of sulfotransferases have been hindered by the lack of a productive recombinant protein expression system. Grand Challenges in Chemistry for 2016 and Beyond. View details for Web of Science ID 000257629200046, View details for PubMedCentralID PMC2664610. Thus, choice of enrichment strategy has profoundimplications on experimental outcomes. I actually started as a premed. In particular, Bertozzi has advanced the understanding of cell surface oligosaccharides involved in cell recognition and inter-cellular communication. Asparagine-linked glycosylation is a common post-translational modification of proteins; in addition to participating in key macromolecular interactions, N-glycans contribute to protein folding, trafficking, and stability. We explored whether unnatural cell surface sialosides produced by metabolism can act as neo-antigens and modulate the immunogenicity of cells.Immunization of rabbits with synthetic conjugates of an unnatural sialic acid bound to keyhole limpet hemocyanin produced significant titers of antibodies that were specific for the structurally altered sialic acid. Finally, we discovered that treatment of mycobacteria with ethambutol, a front-line tuberculosis (TB) drug, significantly increases mycomembrane fluidity. Monomeric and multivalent oligosaccharides that bind to bacterial and viral receptors have been shown to abrogate infection by agents such as Helicobacter pilori, influenza virus and HIV. Sialic acid is a major determinant of carbohydrate-receptor interactions in many systems pertinent to human health and disease. A., Riley, L. W., Bertozzi, C. R. 5 '-Adenosinephosphosulphate reductase (CysH) protects Mycobacterium tuberculosis against free radicals during chronic infection phase in mice. A., Bertozzi, C. R., Gibson, B. W. A small-molecule modulator of poly-alpha 2,8-sialic acid expression on cultured neurons and tumor cells. The measurements indicate a detection limit of (5.6 +/- 1.1) x 10(6) L. monocytogenes in our sample volume of 20 microl. View details for DOI 10.1016/j.chembiol.2004.02.023, View details for Web of Science ID 000220502900010. These included proteins involved in the immune response, oxidation and reduction, and vesicle transport, as well as other cellular processes. Agre, P., Bertozzi, C., Bissell, M., Campbell, K. P., Cummings, R. D., Desai, U. R., Estes, M., Flotte, T., Fogleman, G., Gage, F., Ginsburg, D., Gordon, J. I., Hart, G., Hascall, V., Kiessling, L., Kornfeld, S., Lowe, J., Magnani, J., Mahal, L. K., Medzhitov, R., Roberts, R. J., Sackstein, R., Sarkar, R., Schnaar, R., Schwartz, N., Varki, A., Walt, D., Weissman, I. Mukkamala, R., Kushner, A. M., Bertozzi, C. R. Constructing azide-labeled cell surfaces using polysaccharide biosynthetic pathways. The article will highlight recent approaches to thesynthesis of glycopeptide fragments bearing complex O-linkedglycans, as well as new strategies for the generation of full-lengthglycoproteins. 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