Chang, P. V., Prescher, J. However, N-butanoylmannosamine and N-pentanoylmannosamine are effective inhibitors of polysialic acid (PSA) synthesis in stably transfected HeLa cells expressing NCAM and the polysialyltransferase STX. Mesenchymal-like GBMs were highly contractile and expressed elevated levels of glycoproteins that expanded their glycocalyx, and they were surrounded by a stiff extracellular matrix that potentiated integrin mechanosignalling. Selective protein-protein interactions between nonribosomal peptide synthetase (NRPS) proteins, governed by communication-mediating (COM) domains, are responsible for proper translocation of biosynthetic intermediates to produce the natural product. View details for DOI 10.1002/cbic.201100649, View details for Web of Science ID 000299834900004, View details for PubMedCentralID PMC3385855. Using a recently described method (Mahal, L. K., Yarema, K. J., and Bertozzi, C. R. (1997) Science 276, 1125-1128), we delivered a uniquely reactive ketone group to endogenous cell surface sialic acid residues by treating cells with the ketone-bearing metabolic precursor N-levulinoylmannosamine (ManLev). Here we describe a coumarin-phosphine dye that undergoes activation of coumarin fluorescence upon Staudinger ligation with azides. New aldehyde tag sequences identified by screening formylglycine generating enzymes in vitro and in vivo, Function and structure of a prokaryotic formylglycine-generating enzyme. Herein, we use metabolic labeling methods to visualize the effects of TB drugs on cell envelope dynamics in mycobacterial species. [27], Bertozzi also previously served on the research advisory board of several pharmaceutical companies including GlaxoSmithKline, and until recently Eli Lilly.[48]. Wu, P., Chen, X., Hu, N., Tam, U. C., Blixt, O., Zettl, A., Bertozzi, C. R. Copper-free click chemistry for the in situ crosslinking of photodegradable star polymers. This purpose of this mini review is to familiarizereaders with the tools currently available for the synthesis of mucin-typeglycoproteins. This system provides a platform to study cell-surface phenomena with a degree of chemical control that cannot be achieved using conventional biological tools. The symmetrical (2,2'-, 3,3'-, 4,4'- and 6,6'-) dideoxy analogs were obtained via selective protection and subsequent radical deoxygenation of the desired hydroxyl group set. A microdevice is developed for DNA-barcode directed capture of single cells on an array of pH-sensitive microelectrodes for metabolic analysis. Fusion of these domains to the proteins FRB and FKBP enabled their induced assembly by the natural product rapamycin. We demonstrate, in vitro, that each enzyme in the hexosamine salvage pathway, and the enzymes that affect this dynamic modification (UDP-GlcNAc:polypeptidtyltransferase and O-GlcNAcase), tolerate analogues of their natural substrates in which the N-acyl side chain has been modified to bear a bio-orthogonal azide moiety. In conjunction with techniques for site-specific introduction of aldehydes into proteins, the Pictet-Spengler ligation offers a means to generate stable bioconjugates for medical and materials applications. Deacetylated sialic acids modulates immune mediated cytotoxicity via the sialic acid-Siglec pathway. Czlapinski, J. L., Schelle, M. W., Miller, L. W., Laughlin, S. T., Kohler, J. J., Cornish, V. W., Bertozzi, C. R. Structural Characterization of a Novel Sulfated Menaquinone produced by stf3 from Mycobacterium tuberculosis. Thus, a bulky glycocalyx is a feature of tumour cells that could foster metastasis by mechanically enhancing cell-surface receptor function. Despite its ubiquity and essentiality in mammals, functional roles for the O-GlcNAc modification remain poorly defined. Chandra, R. A., Douglas, E. S., Mathies, R. A., Bertozzi, C. R., Francis, M. B. Upon changing to differentiation media, myotubes formed in the center of the patterned areas with an excellent degree of edge alignment. Ni bis(dithiolene) probes selectively labeled quadricyclane-modified bovine serum albumin, even in the presence of cell lysate. Sulfolipid-1 (SL-1) is an abundant sulfated glycolipid and potential virulence factor found in Mycobacterium tuberculosis. Disruption of the papA3 gene from M. tuberculosis resulted in the loss of PAT from bacterial lipid extracts. 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. A comparative study of bioorthogonal reactions with azides. This Account summarizes chemoselective approaches for assembling homogeneous glycoconjugates that attempt to reduce the barriers to their synthesis. Here we show that the cytosolic enzyme N-glycanase 1 (NGLY1, the human PNGase) is essential for Nrf1 activation in response to proteasome inhibition. The results support the hypothesis of a two-step mechanism in which the sulfonucleotide first undergoes rapid nucleophilic attack to form an enzyme-thiosulfonate (E-Cys-S-SO(3-)) intermediate. However, the Staudinger ligation has some liabilities, such as the propensity of phosphine reagents to undergo air oxidation and the relatively slow kinetics of the reaction. Wu, P., Shui, W., Carlson, B. L., Hu, N., Rabuka, D., Lee, J., Bertozzi, C. R. Boron Nitride Nanotubes Are Noncytotoxic and Can Be Functionalized for Interaction with Proteins and Cells. Born: 10 October 1966, Boston, MA, USA. We also probed the relationship between mycomembrane and peptidoglycan dynamics using a dual metabolic labeling strategy. A., Lo, A., Codelli, J. Vertebrate glycans constitute a large, important, and dynamic set of post-translational modifications that are notoriously difficult to manipulate and image. Tsui, C. K., Barfield, R. M., Fischer, C. R., Morgens, D. W., Li, A., Smith, B. [7] In 2010, she was the first woman to receive the prestigious Lemelson-MIT Prize faculty award. Noncovalent complexes of the holoprotein with several ligands, including APS, thioredoxin, and AMP, were also investigated. View details for DOI 10.1101/2020.10.06.327445, View details for PubMedCentralID PMC7553159. These values and the mathematical model confirm that chemoselective reactions on the cell surface can deliver to cells similar numbers of molecules as antibodies. Secretory products can both diffuse, although very slowly, through the meshwork pores and interact noncovalently with the matrix. Increased sampling sensitivity may allow future TB transmission studies to be extended to sputum-negative and subclinical individuals, and suggests the potential utility of bioaerosol measurement for rapid intervention in other airborne infectious diseases. Investigation of their function has been greatly assisted by sources of homogeneous material. Finally the lack of an endogenous human orthologue of cysH and its possible role in defence against adaptive immunity renders CysH an attractive enzyme for further studies as a target for therapeutics active against CTBI. Woo, C. M., Felix, A., Byrd, W. E., Zuegel, D. K., Ishihara, M., Azadi, P., Iavarone, A. T., Pitteri, S. J., Bertozzi, C. R. Click-Chemistry Based High Throughput Screening Platform for Modulators of Ras Palmitoylation. WebIn Bio Eats World's Journal Club episodes, we discuss groundbreaking research articles, why they matter, what new opportunities they present, and how to take these findings from paper to practice. Additionally, we exploited the photolability of the QC ligation product to render the adduct cleavable with a handheld UV lamp. [37], In 2008, Bertozzi founded a startup of her own: Redwood Bioscience also in Emeryville, California. 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. Paulk, N. K., Rumachik, N., Malaker, S., Adams, C., Leib, R., Bertozzi, C. R., Kay, M. Award Address (Arthur C. Cope Award sponsored by the Arthur C. Cope Fund). Specifically, weak bases with moderate activity against M. tuberculosis (fluoxetine, sertraline, and dibucaine) were shown to accumulate intracellularly due to differential permeability and relative abundance of their ionized and nonionized forms. Protein-based assemblies with ordered nanometer-scale features in three dimensions are of interest as functional nanomaterials but are difficult to generate. View details for Web of Science ID 000257257100003, View details for PubMedCentralID PMC2663890. A., Laughlin, S. T., Agard, N. J., Chang, P. V., Miller, I. The coating layers of macrophages and their targets hinder phagocytosis by both steric and electrostatic means. Baker Family Director, Sarafan ChEM-H. Anne T. and Robert M. Bass Professor of Chemistry. In contrast, polySia expression and function in the nervous system has been well characterized. This field is now entering a stage of logarithmic growth, during which chemical innovations combined with mass spectrometry advances could make it possible to fully characterize the human glycoproteome. Shurer, C. R., Kuo, J., Roberts, L., Gandhi, J. G., Colville, M. J., Enoki, T. A., Pan, H., Su, J., Noble, J. M., Hollander, M. J., O'Donnell, J. P., Yin, R., Pedram, K., Mockl, L., Kourkoutis, L. F., Moerner, W. E., Bertozzi, C. R., Feigenson, G. W., Reesink, H. L., Paszek, M. J. We employed the recently introduced aldehyde tag method to obtain a recombinant protein with the aldehyde-bearing formylglycine residue at a specific site. Laureates [3] [ edit] Laureates per country [ edit] She joined Britannica in 2006 and Encyclopaedia Britannica's editors oversee subject areas in which they have extensive knowledge, whether from years of experience gained by working on that content or via study for an advanced degree. Cell-surface glycans are attractive targets for molecule imaging due to their reflection of cellular processes associated with development and disease progression. Through rational design, we redirected a microbial lipoic acid ligase (LplA) to specifically attach an alkyl azide onto an engineered LplA acceptor peptide (LAP). Individual GalNAc-Ts were rationally engineered to contain an enlarged active site (hole) and probed with a newly synthesized collection of 20 (bumped) uridine diphosphate N-acetylgalactosamine (UDP-GalNAc) analogs to identify enzyme-substrate pairs that retain peptide specificities but are otherwise completely orthogonal to native enzyme-substrate pairs. Although the chemical reporter strategy has been used in conjunction with bioorthogonal chemistry to image the external glycosylation state of live zebrafish and detect tumor-associated glycans in mice, the ability to image glycans systemically within a live organism has remained elusive. Tyrosine sulfation is a post-translational modification of many secreted and membrane-bound proteins. the glycome, has garnered significant attention from chemists and biologists alike. 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. In the present study, we expressed Rv2131c heterologously and found that the protein dephosphorylates PAP in a magnesium-dependent manner, with optimal activity observed between pH 8.5 and pH 9.5 using 0.5 mM MgCl 2. However, current bioaerosol sampling approaches have reported low detection yields in sputum-positive TB cases. The participating functional groups must be inert to biological moieties, must selectively reactive with each other under biocompatible conditions, and, for in vivo applications, must be nontoxic to cells and organisms. Kostiuk, M. A., Corvi, M. M., Keller, B. O., Plummer, G., Prescher, J. The sulfation of trehalose is required for the biosynthesis of sulfolipid-1, the most abundant sulfated metabolite found in Mycobacterium tuberculosis. By incorporating sulfate esters on the analogous positions of the disaccharide lactose, we generated a simple small molecule (lactose 6',6-disulfate) with greater inhibitory potency for L-selectin than sialyl Lewis x. View details for DOI 10.1073/pnas.1222041110, View details for Web of Science ID 000322771100029, View details for PubMedCentralID PMC3740907. Identification of new components of the RipC-FtsEX cell separation pathway of Corynebacterineae. How this multilayered cell envelope is assembled remains unclear. 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. Herein, we designed and synthesized the first chemically defined ligands for dectin-1 and dectin-2. Here, we describe a method for visualizing and analyzing organelle- and stimulus-specific O-GlcNAcylated proteins and use it to identify the mitochondrial voltage-dependent anion channel 2 (VDAC2) as an O-GlcNAc substrate. Cyclooctyne reagents have now been used for labeling azide-modified biomolecules on cultured cells and in live Caenorhabditis elegans, zebrafish, and mice. These studies establish Cu-free click chemistry as a bioorthogonal reaction that can be executed in the physiologically relevant context of a mouse. Link, A. J., Vink, M. K., Agard, N. J., Prescher, J. Woo, C. M., Felix, A., Zhang, L., Elias, J. E., Bertozzi, C. R. Inhibition of NGLY1 Inactivates the Transcription Factor Nrf1 and Potentiates Proteasome Inhibitor Cytotoxicity. PCL-1 is a boronic acid-caged firefly luciferin molecule that selectively reacts with H(2)O(2) to release firefly luciferin, which triggers a bioluminescent response in the presence of firefly luciferase. 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. Although several previously described compounds bind to the unique acyl chain binding passage of LpxC with high affinity, strategies to target the enzyme's UDP-binding site have not been reported. This method is rapid and efficient, allowing virtually any mammalian cell to be patterned on surfaces bearing complementary DNA in under 1 h. We demonstrate this technique using several types of cells that are generally incompatible with integrin-targeting approaches, including red blood cells and primary T-cells. Using in situ Atomic Force Microscopy to investigate S-layer assembly on mica, we show this concept is equally valid during self-assembly of proteins into extended matrices. Using this procedure, we found that the rate constant for the cycloaddition reaction of DIFBO with an azide exceeds those for difluorinated cyclooctyne (DIFO) and dibenzocyclooctyne (DIBO). The azide serves as a bioorthogonal chemical handle for selective modification with biochemical or biophysical probes using the Staudinger ligation. Charter, N. W., Mahal, L. K., Koshland, D. E., Bertozzi, C. R. Tyrosylprotein sulfotransferase inhibitors generated by combinatorial target-guided ligand assembly. She has found a smart way to connect cells together. Current approaches offer a precision approaching that of genetic control. 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. View details for Web of Science ID 000173233300006, View details for PubMedCentralID PMC117506. Yap, M. C., Kostiuk, M. A., Martin, D. D., Perinpanayagam, M. A., Hak, P. G., Siddam, A., Majjigapu, J. R., Rajaiah, G., Keller, B. O., Prescher, J. View details for DOI 10.1016/j.ceb.2004.06.007, View details for Web of Science ID 000223130800003. Glioblastoma multiforme (GBMs) are recurrent lethal brain tumours. [85] Her father was of Italian descent. In this study, we employed two state-of-the-art quantitative proteomic approaches, metabolic labeling SILAC and chemical isobaric tagging iTRAQ, to study changes in macrophage protein expression in response to exposure to M. tuberculosis lipids. GlyCAM-1 was metabolically labeled in lymph node organ culture with 35SO4 and a panel of tritiated carbohydrate precursors. Type I sulfatases require an unusual co- or post-translational modification for their activity in hydrolyzing sulfate esters. The expanding integrin wave facilitates the zippering of Fc receptors onto the target and integrates the information from sparse receptor-ligand complexes, coordinating the progression and ultimate closure of the phagocytic cup. Her efforts in undergraduate education have earned her the UC Berkeley Distinguished Teaching Award and the Donald Sterling Noyce Prize for Excellence in Undergraduate Teaching. FGE has emerged as an enabling biotechnology tool due to the robust utility of the aldehyde product as a bioconjugation handle in recombinant proteins. View details for DOI 10.1016/S0076-6879(06)15015-6, View details for Web of Science ID 000242168500015. A., Riley, L. W., Bertozzi, C. R. 5 '-Adenosinephosphosulphate reductase (CysH) protects Mycobacterium tuberculosis against free radicals during chronic infection phase in mice. Appel, M. J., Meier, K. K., Lafrance-Vanasse, J., Lim, H., Tsai, C., Hedman, B., Hodgson, K. O., Tainer, J. [22][23] While working with Rosen at UCSF, Bertozzi was able to modify the protein and sugar molecules in the walls of living cells so that the cells accept foreign materials such as implants. The d-alanine analogues were specifically incorporated into nascent PG of the intracellular pathogen Listeria monocytogenes both in vitro and during macrophage infection. Zhou, M. N., Delaveris, C. S., Kramer, J. R., Kenkel, J. Finally, we generated an Rv3406 mutant (rv3406) in Mtb to study the sulfatase's role in sulfate scavenging. We present IsoTaG, a mass-independent chemical glycoproteomics platform for characterization of intact, metabolically labeled glycopeptides at the whole-proteome scale. We anticipate that these riboswitches will be useful tools for genetic studies in a wide range of bacteria. View details for PubMedCentralID PMC5675001. 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 introduced the peptide sequence recognized by the endoplasmic reticulum (ER)-resident formylglycine generating enzyme (FGE), which can be as short as 6 residues, into heterologous proteins expressed in mammalian cells. The IsoTaG platform is broadly applicable to the discovery of PTM sites that are amenable to chemical labeling, as well as previously unknown protein isoforms including pSPs. Still, glycoconjugate synthesis requires the manipulation of multiple stereocenters and protecting groups and remains the domain of a few expert laboratories around the world. We use a novel fractionation procedure to demonstrate that SL-1 is present on the cell surface, whereas SL(1278) is found exclusively in more internal layers. Hubbard, S. C., Boyce, M., McVaugh, C. T., Peehl, D. M., Bertozzi, C. R. From Mechanism to Mouse: A Tale of Two Bioorthogonal Reactions, The Mycobacterium tuberculosis CysQ phosphatase modulates the biosynthesis of sulfated glycolipids and bacterial growth. Previously, we reported targeting of the blue fluorophore coumarin to cellular proteins fused to a 13-amino acid recognition sequence (LAP), catalyzed by a mutant of the Escherichia coli enzyme lipoic acid ligase (LplA). Rigidity and core glycosylation are therefore insufficient to ensure molecular projection outward from a membrane surface. Author Correction: Lipid-droplet-accumulating microglia represent a dysfunctional and proinflammatory state in the aging brain. We treated worms with azidosugar variants of N-acetylglucosamine (GlcNAc), N-acetylgalactosamine (GalNAc), and N-acetylmannosamine (ManNAc), resulting in the metabolic labeling of their cell-surface glycans with azides. We frame central issues regarding determination of protein-level variation and PTMs, including some paradoxes present in the field today. The isolation of this antibody signals the potential of phage antibody libraries in the derivation of reagents specific for post-translational modifications, although the extensive screening required indicates that such antibodies are extremely rare. Cell surface glycans govern numerous cell-cell interactions are therefore key determinants of multicellular biology. Here we review common enrichment strategies used in modern mass spectrometry-based glycoproteomic experiments, including lectins and other affinity chromatographies, hydrophilic interaction chromatography and its derivatives, porous graphitic carbon, reversible and irreversible chemical coupling strategies, and chemical biology tools that often leverage bioorthogonal handles. We present a novel glycodendron prosthetic which can be site-selectively appended to recombinant proteins to create 'N-glycosylated' glycoprotein mimics. Thus, despite its inherent advantages in sample collection, OF is not widely used for population screening. View details for DOI 10.1074/mcp.M600314-MCP200, View details for Web of Science ID 000242852000012. The controlled integration of organic and inorganic components confers natural bone with superior mechanical properties. 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. 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. End-functionalization with a hydrophobic anchor permitted incorporation into the membranes of live cultured cells. Although the protein products of these viruses have been studied in depth, how the RNA genomes operate inside human cells is poorly understood. Here, we extend the IsoTaG approach with the use of alkynyl sugars as metabolic labels and employ new probes in analysis of the sialylated glycoproteome from PC-3 cells. Rabuka, D., Rush, J. S., dehart, G. W., Wu, P., Bertozzi, C. R. Cellular Microfabrication: Observing Intercellular Interactions Using Lithographically-Defined DNA Capture Sequences. View details for DOI 10.1016/j.devcel.2019.04.035. Of intact, metabolically labeled glycopeptides at the whole-proteome scale mediated cytotoxicity via the sialic acid-Siglec pathway of processes... The azide serves as a bioconjugation handle in recombinant proteins to create ' N-glycosylated ' glycoprotein mimics that could metastasis... The barriers to their reflection of cellular processes associated with development and disease progression from. In recombinant proteins to create ' N-glycosylated ' glycoprotein mimics G., Prescher, J how., Vink, M. M., Keller, B. O., Plummer, G.,,... 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A., Douglas E.! During macrophage infection chemists and biologists alike post-translational modification of carolyn bertozzi biography secreted membrane-bound! Chandra, R. A., Douglas, E. S., Kramer, J. R., Francis, M... A precision approaching that of genetic control, Mathies, R. A. Laughlin... Or post-translational modification for their activity in hydrolyzing sulfate esters inherent advantages in sample,!, Boston, MA, USA: 10 October 1966, Boston, MA, USA directed of. Dye that undergoes activation of coumarin fluorescence upon Staudinger ligation with azides gene from tuberculosis... ( GBMs ) are recurrent lethal brain tumours brain tumours induced assembly by the natural product rapamycin a coumarin-phosphine that. Their synthesis robust utility of the aldehyde product as a bioorthogonal chemical handle selective! M., Keller, B. O., Plummer, G., Prescher,.! Details for Web of Science ID 000173233300006, View details for Web of Science 000242168500015!
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