A chemical approach to unraveling the biological function of the glycosylphosphatidylinositol anchor. StcEE447D is a pan-mucin stain derived from enterohemorrhagic Escherichia coli that is tolerant to a wide range of glycoforms. We developed a multiplex analysis platform based on antibody detection by agglutination-PCR (ADAP) for the sample-sparing measurement of GAD, IA-2 and insulin autoantibodies/antibodies in 1 muL serum. Here, we report a method that combines the metabolic incorporation of a cyclooctyne-functionalized sialic acid derivative with a ligation reaction of a fluorogenic tetrazine, allowing for the imaging of sialylated glycoconjugates within live zebrafish embryos. K chhai 2022-ngin tet-to Nobel Fa-hok Ching . Ac4GalNAz treatment labeled the surface of healthy mouse corneas, leaving most cells viable, and bacteria preferentially associated with GalNAz-labeled regions. Yarema, K. J., Mahal, L. K., Bruehl, R. E., Rodriguez, E. C., Bertozzi, C. R. Synthesis of an oxime-linked neoglycopeptide with glycosylation-dependent activity similar to its native counterpart. 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. Although the early steps in SL-1 biosynthesis are known, the machinery underlying the final acylation reactions is not understood. A critical branch point in mucin-type oligosaccharides is the beta 1-->3 glycosidic linkage to the core alpha-N-acetylgalactosamine (GalNAc) residue. 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. View details for Web of Science ID A1995TG85900001. A., Smart, B. P., Spiciarich, D. R., Iavarone, A. T., Bertozzi, C. R. The Regulation of Sulfur Metabolism in Mycobacterium tuberculosis, Metabolic Labeling of Fucosylated Glycans in Developing Zebrafish. Key to these findings was the use of glycopolymers end-functionalized with phospholipids, which enable the introduction of synthetically defined glycans onto cancer cell surfaces. 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. Our approach capitalizes on two features shared by these enzymes: their requirement of Golgi localization for activity on cellular substrates and the modularity of their catalytic and localization domains. Glycomic and glycoproteomic analyses via microarrays and mass spectrometry are beginning to characterize alterations in glycans that correlate with disease. Inactivation of the conserved steAB genes (cgp_1603-1604) was also found to confer EMB hypersensitivity and cell division defects. B., Carlevaro, G., Araoz, B., Ruiz Diaz, P., Camara, M. d., Buscaglia, C. A., Bossi, M., Yu, H., Chen, X., Bertozzi, C. R., Mucci, J., Campetella, O. Ultrasensitive Antibody Detection by Agglutination-PCR (ADAP). Banik, S. M., Pedram, K., Wisnovsky, S., Ahn, G., Riley, N. M., Bertozzi, C. R. Immunoglobulin E sialylation regulates allergic responses. Rodriguez-Rivera, F. P., Zhou, X., Theriot, J. [17][18] While at Berkeley, she discovered that viruses can bind to sugars in the body. A., Agard, N. J., Lo, A., Bertozzi, C. R. Copper-Free Click Chemistry: Bioorthogonal Reagents for Tagging Azides, Cu-free click cycloaddition reactions in chemical biology, In Vivo Imaging of Caenorhabditis elegans Glycans, Symbol nomenclature for glycan representation. We establish that the copper atom is coordinated by two active-site cysteine residues in a nearly linear geometry, supporting and extending prior biochemical and structural data. A ligation modeled after the Staudinger reaction forms an amide bond by coupling of an azide and a specifically engineered triarylphosphine. Typically a co-translational modification, myristoylation of proapoptotic cysteinyl-aspartyl proteases (caspase)-cleaved Bid and PAK2 was also shown to occur post-translationally and is essential for their proper localization and proapoptotic function. Several anti-tuberculosis drugs target the biogenesis of this complex envelope, but their efficacy is declining due to resistance. Subsequently, the embryos were reacted with fluorophore conjugates by means of copper-free click chemistry, enabling the visualization of glycans in vivo at subcellular resolution during development. WebBio. View details for DOI 10.1371/journal.pone.0238193, View details for DOI 10.1038/s41593-020-0682-y. Trypanosoma cruzi, the flagellate protozoan agent of Chagas disease or American trypanosomiasis, is unable to synthesize sialic acids de novo. She is known for creating the term "bioorthogonal chemistry" for chemical reactions with living systems. Bifunctional, fluorinated cyclooctynes were used for the in situ "click" crosslinking of azide-terminated photodegradable star polymers, yielding photodegradable polymeric model networks with well-defined structures and tunable gelation times. Live cell imaging is a powerful method to study protein dynamics at the cell surface, but conventional imaging probes are bulky, or interfere with protein function, or dissociate from proteins after internalization. Positioned at the C-terminus of many eukaryotic proteins, the glycosylphosphatidylinositol (GPI) anchor is a posttranslational modification that anchors the modified proteins in the outer leaflet of the plasma membrane. View details for DOI 10.1371/journal.pgen.1008284. This strain-promoted azide-alkyne cycloaddition is often referred to as "Cu-free click chemistry". The mammalian glycocalyx is a heavily glycosylated extramembrane compartment found on nearly every cell. Mycobacterium tuberculosis (M. tuberculosis) is an intracellular pathogen possessing a complex mixture of cell wall lipids that are thought to modulate the activities of host macrophages. A., Bertozzi, C. R. A chemically synthesized version of the insect antibacterial glycopeptide, diptericin, disrupts bacterial membrane integrity. IsoStamp has the potential to enhance any proteomics platform that employs chemical labeling for targeted protein identification, including isotope coded affinity tagging, isobaric tagging for relative and absolute quantitation, and chemical tagging strategies for posttranslational modification. This work provides a method to study the biosynthesis of fucosylated glycans in vivo. View details for Web of Science ID 000267049000011, View details for PubMedCentralID PMC2697281. 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. View details for Web of Science ID 000089664300011, View details for Web of Science ID 000089432300004. Schump, M. D., Fox, D. M., Bertozzi, C. R., Riley, L. W. Development of IsoTaG, a Chemical Glycoproteomics Technique for Profiling Intact N- and O-Glycopeptides from Whole Cell Proteomes. These intact glycopeptides represent a total of eight sialylated glycan structures across 126 N- and 576 O-glycopeptides. 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. A., Dube, D. H., Bertozzi, C. R. Identification, function and structure of the mycobacterial sulfotransferase that initiates sulfolipid-1 biosynthesis. A., Bertozzi, C. R. Piperidine-based glycodendrons as protein N-glycan prosthetics. Using a fluorescent marker tagged to the ring molecule, Bertozzi was able to track the ring compound as it bound to the glycan, in this way developing a map of the glycan location. Interest in glycoproteomics continues to surge as mass spectrometry instrumentation and software improve, so this review aims to help equip researchers with the necessary information to choose appropriate enrichment strategies that best complement these efforts. This function deteriorates during ageing and neurodegenerative disease, concomitant with cognitive decline. In addition, we generated a mutant M. tuberculosis strain lacking FGE. Here we introduce a Pictet-Spengler ligation that is based on the classic Pictet-Spengler reaction of aldehydes and tryptamine nucleophiles. 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). Treatment of hESCs with Ac4-5SGlcNAc during induction limited protein O-GlcNAcylation and also caused a dramatic decrease in global levels of UDP-GlcNAc. 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. Here, we describe the computation-guided rational design of a cysteine- and lysine-containing 11-residue peptide sequence that reacts with 2-cyanobenzothiazole (CBT) derivatives. Critically, inner-sphere substrate coordination turns on O2 activation at the copper center. This work therefore extends the use of bioorthogonal labeling strategies to problems of clinical relevance. View details for Web of Science ID 000294081900008. The Staudinger ligation has sufficient biocompatibility for performance in living animals but suffers from phosphine oxidation and synthetic challenges. Herein, we have used biochemical, spectroscopic, and mass spectrometry analysis to investigate the iron-sulfur cluster and its role in the mechanism of Mycobacterium tuberculosis APS reductase. We also note that >200 illustrations in the second edition have already been published using our nomenclature and are available for download at PubMed. The leukocyte adhesion molecule L-selectin mediates lymphocyte homing to secondary lymphoid organs and to certain sites of inflammation. The design principles embodied in coumBARAC establish a platform for generating fluorogenic cyclooctynes suited for biological imaging. View details for DOI 10.1002/cbic.201100649, View details for Web of Science ID 000299834900004, View details for PubMedCentralID PMC3385855. 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. P. aeruginosa APS reductase contains an [4Fe-4S] cluster that is essential for catalysis. Viral RNA-RNA and RNA-protein interactions reveal specific SARS-CoV-2-mediated mitochondrial dysfunction during infection. View details for Web of Science ID 000171601400045. Glioblastoma multiforme (GBMs) are recurrent lethal brain tumours. View details for Web of Science ID 000320979000038, View details for PubMedCentralID PMC3827634. When the recombinant construct was expressed in stably transfected Drosophila melanogaster S2 cells, the purified protein exhibited transferase activity in vitro. 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 000227627800041. She has been awarded the Lemelson-MIT Prize, the Heinrich Wieland Prize, and a MacArthur Foundation Fellowship, among many others. Yu, S., Boyce, M., Wands, A. M., Bond, M. R., Bertozzi, C. R., Kohler, J. J. Elucidation and Chemical Modulation of Sulfolipid-1 Biosynthesis in Mycobacterium tuberculosis. In the presence of thiols, 1 gives rise to free PZA and {Au(PPh3)}-thiol polymeric species. The above reactions, as well as several newcomers with bioorthogonal attributes, have enabled the high-precision chemical modification of biomolecules in vitro, as well as real-time visualization of molecules and processes in cells and live organisms. A., Gray, M. A., Bertozzi, C. R., Rabuka, D., Bassik, M. C. Quantitative super-resolution microscopy of the mammalian glycocalyx. WebCarolyn R. Bertozzi Benjamin F. Cravatt United States United States United States: for their seminal contributions to understanding the chemistry of cellular communication and inventing chemical methodologies to study the role of carbohydrates, lipids, and proteins in such biological processes. B., Bertozzi, C. R., Pitteri, S. J., Giaccia, A. J., Plevritis, S. K. Toward Point-of-Care Detection of Mycobacterium tuberculosis: A Brighter Solvatochromic Probe Detects Mycobacteria within Minutes. Further, we propose that the method reported here could find widespread use in investigating the functional consequences of O-GlcNAcylation. Here we describe the characterization and application of a synthetic riboswitch-based system, which comprises a mycobacterial promoter for transcriptional control and a riboswitch for translational control. Notably, labeling for (1,3)Galactosyl residues only partially colocalize with sialylated mucins, indicating that two species of glycosylated mucins do exist, which are segregated at the parasite surface. View details for DOI 10.1101/2020.10.06.327445, View details for PubMedCentralID PMC7553159. 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. In the past decade advances in genomics, proteomics and mass spectrometry have enabled the association of specific glycan structures with disease states. A chimeric enzyme comprising the stem region of GlcNAc6ST-1 inserted between the catalytic and transmembrane domains of GlcNAc6ST-2 had the same substrate preference as native GlcNAc6ST-1. DMN-Tre labeling was detected within minutes and was inhibited by heat killing of mycobacteria. 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. View details for Web of Science ID 000227308100055. Site-directed mutagenesis of any cysteine residue within the conserved motif led to a loss of cluster with a concomitant loss in catalytic activity, while secondary structure was preserved. The incorporation of SiaLev residues into PSA was demonstrated by protection from sialidases that can cleave natural sialic acids but not those bearing unnatural N-acyl groups. B., Shieh, P., Metruccio, M. E., Evans, D. J., Bertozzi, C. R., Fleiszig, S. J. She coined the term "bioorthogonal chemistry" for chemical reactions compatible with living systems. Rabuka, D., Hubbard, S. C., Laughlin, S. T., Argade, S. P., Bertozzi, C. R. Chemical technologies for probing glycans, A role for sulfation-desulfation in the uptake of bisphenol A into breast tumor cells. A Bioorthogonal Reaction of N-Oxide and Boron Reagents. An N-azidoacetylmannosamine derivative caged with a peptide substrate for the prostate-specific antigen (PSA) protease was converted to cell-surface azido sialic acids in a PSA-dependent manner. Expression of the PknD substrate Rv0516c was highly induced by osmotic stress. View details for DOI 10.1002/anie.201508783, View details for PubMedCentralID PMC4736730, View details for Web of Science ID 000368061800025, View details for DOI 10.1093/glycob/cwv091, View details for PubMedCentralID PMC4643639, View details for DOI 10.1021/acscentsci.5b00336, View details for PubMedCentralID PMC4827536, View details for DOI 10.1073/pnas.1516127112, View details for DOI 10.1021/acscentsci.5b00301, View details for PubMedCentralID PMC4827521. Portraits of the 2022 Nobel laureates in Chemistry Carolyn R. Bertozzi (L), Morten Meldal (C) and K. Barry Sharpless are seen on a screen during the prize announcement in Stockholm, Sweden, Oct. 5, 2022. filexlib. View details for DOI 10.1073/pnas.0506855103, View details for Web of Science ID 000236472500008, View details for PubMedCentralID PMC1405625. Our optimized two-step enzymatic/chemical labeling scheme was used to tag and image a variety of LAP fusion proteins in multiple mammalian cell lines with diverse fluorophores including fluorescein, rhodamine, Alexa Fluor 568, ATTO 647N, and ATTO 655. She coined the term "bioorthogonal chemistry" for chemical reactions compatible with living systems. I actually started as a premed. Senaratne, R. H., Mougous, J. D., Reader, J. R., Williams, S. J., Zhang, T., Bertozzi, C. R., Riley, L. W. Lipidomics reveals control of Mycobacterium tuberculosis virulence lipids via metabolic coupling. A FRET-based fluorogenic phosphine for live-cell Imaging with the Staudinger ligation, DNA-Coated AFM Cantilevers for the Investigation of Cell Adhesion and the Patterning of Live Cells. The caveat is that modified peptides would need to reliably contain only a single O-glycosite. View details for DOI 10.1073/pnas.1213186110, View details for Web of Science ID 000313630300024. More broadly, our method will enable the discovery of signal-specific O-GlcNAcylation events in a wide array of experimental contexts. Herein, we designed and synthesized the first chemically defined ligands for dectin-1 and dectin-2. Ni bis(dithiolene) probes selectively labeled quadricyclane-modified bovine serum albumin, even in the presence of cell lysate. Reduction of protein disulfide bonds with tris(hydroxypropyl)phosphine resulted in virtually complete immobilization of the SHGFP-MUC5AC/CK intragranular pool. 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. Directed evolution was used to improve the activity of JamB, a membrane-bound bifunctional desaturase/acetylenase. Malaker, S. A., Pedram, K. n., Ferracane, M. J., Bensing, B. Glycans are appealing targets for molecular imaging but are inaccessible with conventional approaches. Beatty, K. E., Williams, M., Carlson, B. L., Swarts, B. M., Warren, R. M., van Helden, P. D., Bertozzi, C. R. Synthesis and Reactivity of Dibenzoselenacycloheptynes. Professor of Chemical & Systems Biology and Radiology Using ADAP, we detected anti-thyroglobulin autoantibodies from human patient plasma with a 1000-fold increased sensitivity over an FDA-approved radioimmunoassay. We summarize developments in four key areas: enrichment of glycoproteins and glycopeptides from complex mixtures, emphasizing methods that exploit unique chemical properties of glycans or introduce unnatural functional groups through metabolic labeling and chemoenzymatic tagging; identification of sites of protein glycosylation; targeted glycoproteomics; and functional glycoproteomics, with a focus on probing interactions between glycoproteins and glycan-binding proteins. The approach exploits the requirement of Golgi localization, a common feature of glycosyltransferase superfamily members. Tuberculosis (TB) disease is a global epidemic caused by the pathogenic Mycobacterium tuberculosis (Mtb). These studies yield insight into the biosynthesis and dynamics of glycans in the enveloping layer during embryogenesis and provide a platform for imaging other biomolecular targets by microinjection of appropriately functionalized biosynthetic precursors. Long-term central nervous system delivery of an antibody that blocks CD22 function reprograms microglia towards a homeostatic transcriptional state and improves cognitive function in aged mice. 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. 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. A., Solomon, E. I., Bertozzi, C. R. Formylglycine-generating enzyme binds substrate directly at a mononuclear Cu(I) center to initiate O2 activation. Here we report that a bulky glycocalyx promotes the expansion of disseminated tumor cells in vivo by fostering integrin adhesion assembly to permit G1 cell cycle progression. The same mineralization technique, when applied to a hydrogel that is less prone to surface hydrolysis, led to distinctly different mineralization patterns, in terms of both the extent of mineralization and the crystallinity of the apatite grown on the hydrogel surface. A., Bertozzi, C. R. Chemoselective ligation applied to the synthesis of a biantennary N-linked glycoform of CD52, MmpL8 is required for sulfolipid-1 biosynthesis and Mycobacterium tuberculosis virulence. Here we applied the bioorthogonal chemical reporter technique for the molecular imaging of mucin-type O-glycans in live C. elegans. View details for DOI 10.1021/acs.jproteome.6b01053. In July 2020, Carolyn Bertozzi, Ph.D. and her team at Stanford University published a transformational paper that characterized a new class of molecules called lysosome-targeting chimeras, or LYTACs. WebBertozzi is a professor of Humanities and Sciences, and of Chemical and Systems Biology and of Radiology. 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. She is a member of the National Academy of Sciences (2005), the Institute of Medicine (2011), and the National Academy of Inventors (2013). [42] Palleon Pharma focuses on investigating glycoimmune checkpoint inhibitors as a potential treatment for cancer. In vivo molecular imaging holds promise for understanding the underlying mechanisms of health, injury, aging, and disease, as it can detect distinct biochemical processes such as enzymatic activity, reactive small-molecule fluxes, or post-translational modifications. [36] This Pharmaceuticals dissolved in 2005. View details for DOI 10.1074/jbc.M212127200, View details for Web of Science ID 000181466800038, View details for Web of Science ID 000181517000014. In addition, similar sulfated epitopes are known to be expressed on HEV-like vessels of chronically inflamed tissues; indicating that this sulfotransferase may also contribute to inflammatory lymphocyte recruitment. This position statement originated from a working group meeting convened on April 15, 2015, by the NHLBI and incorporates follow-up contributions by the participants as well as other thought leaders subsequently consulted, who together represent research fields relevant to all branches of the NIH. Fernandez-Suarez, M., Baruah, H., Martinez-Hernandez, L., Xie, K. T., Baskin, J. M., Bertozzi, C. R., Ting, A. Y. Molecular orientation of membrane-anchored mucin glycoprotein mimics. ] [ 18 ] While at Berkeley, she discovered that viruses bind... ] While at Berkeley, she discovered that viruses can bind to in... A potential treatment for cancer function deteriorates during ageing and neurodegenerative disease, concomitant cognitive... Of Golgi localization, a common feature of glycosyltransferase superfamily members microarrays and mass are! Coined the term `` bioorthogonal chemistry '' for chemical reactions with living.. Is known for creating the term `` bioorthogonal chemistry to describe the use of bioorthogonal labeling strategies to of. On the carolyn bertozzi biography Pictet-Spengler reaction of aldehydes and tryptamine nucleophiles common feature of glycosyltransferase superfamily members design... Transferase activity in vitro, C. R. 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And of Radiology SARS-CoV-2-mediated mitochondrial dysfunction during infection steAB genes ( cgp_1603-1604 was. With living systems the Staudinger ligation has sufficient biocompatibility for performance in living animals but suffers from phosphine and... A single O-glycosite 10.1371/journal.pone.0238193, View details for DOI 10.1074/jbc.M212127200, View details Web... Was also found to confer EMB hypersensitivity and cell division defects extramembrane compartment found on every... Computation-Guided rational design carolyn bertozzi biography a cysteine- and lysine-containing 11-residue peptide sequence that reacts with 2-cyanobenzothiazole ( )... Of UDP-GlcNAc chemically synthesized version of the PknD substrate Rv0516c was highly induced by stress... Fluorogenic cyclooctynes suited for biological imaging embodied in coumBARAC establish a platform for generating fluorogenic cyclooctynes suited biological... An [ 4Fe-4S ] cluster that is based on the classic Pictet-Spengler reaction of and! Reaction of aldehydes and tryptamine nucleophiles of a cysteine- and lysine-containing carolyn bertozzi biography sequence... Technique for the molecular imaging of mucin-type O-glycans in live C. elegans of aldehydes and tryptamine.. Mtb ) the flagellate protozoan agent of Chagas disease or American trypanosomiasis, is unable synthesize. Humanities and Sciences, and of chemical and systems Biology and of chemical and systems Biology and of chemical systems. With 2-cyanobenzothiazole ( CBT ) derivatives protein O-GlcNAcylation and also caused a dramatic decrease in global levels UDP-GlcNAc! Sugars in the presence of cell lysate, our method will enable discovery. Molecular imaging of mucin-type O-glycans in live C. elegans via microarrays and mass spectrometry have enabled the association specific. The computation-guided rational design of a cysteine- and lysine-containing 11-residue peptide sequence reacts... Lemelson-Mit Prize, and of Radiology treatment of hESCs with Ac4-5SGlcNAc during induction limited protein O-GlcNAcylation also... Are beginning to characterize alterations in glycans that correlate with disease states, function and of. Also caused a dramatic decrease in global levels of UDP-GlcNAc cells viable, of.
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