The rv3406 strain did not replicate in minimal media with 2-ethyl hexyl sulfate as the sole sulfur source, in contrast to wild type Mtb or the complemented strain. We observed crosslinking between FG-repeat nucleoporins and nuclear transport factors, suggesting that O-GlcNAc residues are intimately associated with essential recognition events in nuclear transport. A. The azide serves as a bioorthogonal chemical handle for selective modification with biochemical or biophysical probes using the Staudinger ligation. Together with previous studies, these findings suggest that this redox cofactor may play a role in mycobacterial pathogenesis. A Bioorthogonal Reaction of N-Oxide and Boron Reagents. The importance of nonclassical, multistage crystallization pathways is increasingly evident from theoretical studies on colloidal systems and experimental investigations of proteins and biomineral phases. Conversely, ETD-based methods, especially EThcD, are indispensable for site-specific analyses of O-glycopeptides. No BPAS is found inside the cells. These findings functionally link mucinous proteins with tumor aggression, and offer a new view of the cancer glycocalyx as a major driver of disease progression. In particular, we focused on biarylazacyclooctynone (BARAC) because it reacts with azides faster than any other reported cyclooctyne and its modular synthesis facilitated rapid access to analogues. Cao, L., Petrone, A., Gatlin, W., Che, J., Das, A., LeBlanc, R., Siddiquee, Z., Nerle, S., Stanczak, M., Mayo, M., Xu, L., Normington, K., Brown, J., Yao, W., Bertozzi, C., Broderick, J., Laubli, H., Peng, L. Physical Principles of Membrane Shape Regulation by the Glycocalyx. The protective efficacy of the current Mycobacterium bovis bacille Calmette-Gurin (BCG) vaccine is highly variable. Intact glycopeptides are recovered by cleavage of the probe, analyzed with directed MS, and assigned by targeted mass-independent data analysis. This technique, which is described in detail, provides a direct measurement of the energy that is released nonradiatively following photostimulation, and can therefore be used to indirectly determine the amount of energy released via luminescent pathways. and Irmgard Chu Distinguished Professorship in Chemistry, UC Berkeley (2005-14), Agnes Fay Morgan Research Award, Iota Sigma Pi (2004), Fellow, American Association for the Advancement of Science (2002), Irving Sigal Young Investigator Award, Protein Society (2002), Donald Sterling Noyce Prize for Excellence in Undergraduate Teaching, UC Berkeley College of Chemistry (2001), Department of Chemistry Teaching Award, UC Berkeley (2000), Merck Academic Development Program Award, Merck (2000), Presidential Early Career Award in Science and Engineering (PECASE), The U.S. White House (2000), Camille Dreyfus Teacher-Scholar Award, Camille and Henry Dreyfus Foundation (1999), Beckman Young Investigator Award, Arnold and Mabel Beckman Foundation (1998), Glaxo Wellcome Scholar, Glaxo Wellcome (1998), Prytanean Faculty Award, Prytanean Women's Honor Society, UC Berkeley (1998), Research Innovation Award, Research Corporation (1998), Young Investigator Award, Office of Naval Research (1998), Horace S. Isbell Award in Carbohydrate Chemistry, American Chemical Society (1997), New Investigator Award in Pharmacology, Burroughs Wellcome (1997), Sloan Research Fellow, Alfred P. Sloan Foundation (1997), Pew Scholars Award in the Biomedical Sciences, Pew Charitable Trusts (1996), Young Investigator Award, Exxon Education Fund (1996), Dreyfus New Faculty Award, Camille and Henry Dreyfus Foundation (1995), Member, National Academy of Inventors (2013 - Present), Member, Institute of Medicine (2011 - Present), Member, German Academy of Sciences Leopoldina (2008 - Present), Member, National Academy of Sciences (2005 - Present), Member, American Academy of Arts and Sciences (2003 - Present), Chair, Scientific Advisory Board, Redwood Bioscience, Board Member, Board of Scientific Counslors, Broad Institutue, Board Member, Research Advisory Baord, Glaxo Smithkline, AB, Harvard University, Chemistry (1988), Membrane curvature regulates the spatial distribution of bulky glycoproteins. Corrections? 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. Using these probes, we studied the mobilities of labeled glycolipids by time-lapse microscopy and fluorescence recovery after photobleaching experiments and found that mycomembrane fluidity varies widely across species and correlates with mycolic acid structure. Illumination of dye-labeled structures generates singlet oxygen to locally catalyze the polymerization of diaminobenzidine into an osmiophilic reaction product that is readily imaged by EM. This enzyme is also the first characterized ppGalNAc-T of protozoan origin. 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. Nuclear repartitioning of galectin-1 by an extracellular glycan switch regulates mammary morphogenesis. Furthermore, their dynamic behavior in synthetic membranes mirrored that of natural biomolecules. View details for DOI 10.1021/acscentsci.6b00070, View details for PubMedCentralID PMC4827488. Woodruff, P. J., Carlson, B. L., Siridechadilok, B., Pratt, M. R., Senaratne, R. H., Mougous, J. D., Riley, L. W., Williams, S. J., Bertozzi, C. R. Syntheses of 6-sulfo sialyl Lewis X glycans corresponding to the L-selectin ligand "Sulfoadhesin", Deconvoluting the functions of polypeptide N-alpha-acetylgalactosaminyltransferase family members by glycopeptide substrate profiling. Kehoe, J. W., Velappan, N., Walbolt, M., Rasmussen, J., King, D., Lou, J., Knopp, K., Pavlik, P., Marks, J. D., Bertozzi, C. R., Bradbury, A. R. Substrate recognition, protein dynamics, and iron-sulfur cluster in Pseudomonas aeruginosa adenosine 5 '-phosphosulfate reductase. [27][44], She co-founded Grace Science Foundation in 2018. A major drawback to studying the sialylation kinetics and turnover of the trypomastigote glycoconjugates is the difficulty to identify and follow the recently acquired sialyl residues. The screening approach described here provides an integrated platform to identify specific modulators of palmitoylated proteins, demonstrated here for Ras and Fyn, but potentially applicable to pharmaceutical targets involved in a variety of human diseases. 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. [13] While an undergraduate, she played in several bands, notably Bored of Education with future Rage Against the Machine guitarist Tom Morello. View details for DOI 10.1074/jbc.M405709200, View details for Web of Science ID 000223791500101, View details for Web of Science ID 000225338800003. Potential for therapeutics and diagnostics, Kinetic measurements and mechanism determination of Stf0 sulfotransferase using mass spectrometry. Surprisingly, 6', 6-disulfolactose was poorly recognized by MECA-79, a carbohydrate- and sulfate-dependent monoclonal antibody that binds competitively to L-selectin ligands. The structure of CysN*D shows the two proteins in tight association; however, the nucleotides bound to each subunit are spatially segregated. Chen, X., Wu, P., Rousseas, M., Okawa, D., Gartner, Z., Zettl, A., Bertozzi, C. R. DNA-barcode directed capture and electrochemical metabolic analysis of single mammalian cells on a microelectrode array. 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. 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. One of the more remarkable lipids is a sulfated glycolipid, termed sulfolipid-1 (SL-1), which is thought to mediate specific host-pathogen interactions during infection. Dr. Bertozzi completed her undergraduate degree in Chemistry at Harvard University and her Ph.D. at 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 postulate that covalent modification and perhaps inhibition of various mitochondrial enzymes by palmitoyl-CoA could lead to the metabolic impairments found in obesity-related diseases. 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. Van de Bittner, G. C., Bertozzi, C. R., Chang, C. J. A general method is described to sequester peptides containing azides from complex peptide mixtures, aimed at facilitating mass spectrometric analysis to study different aspects of proteome dynamics. 1-68A and a 2-dehydroxy analogue, 1-68Aa, inhibit several purified LpxC orthologues. Ac4GalNAz treatment labeled the surface of healthy mouse corneas, leaving most cells viable, and bacteria preferentially associated with GalNAz-labeled regions. Here, we report technology for covalent, specific tagging of cellular proteins with chemical probes. The GPI-protein analogs also diffused freely in cellular membranes. The combination of novel biochemical and metabolism-based approaches with emerging genomic methods promises to accelerate efforts to understand glycosylation. Zurich (2009); Harrison Howe Award (2009); W. H. Nichols Award (2009); Willard Gibbs Medal (2008); Elected member of the German Academy of Sciences Leopoldina (2008); Roy L. Whistler International Award in Carbohydrate Chemistry (2008); Li Ka Shing Women in Science Award (2008); Ernst Schering Prize (2007); Elected member of the National Academy of Sciences (2005); T.Z. However, currently available agonists are heterogeneous glycoconjugates and polysaccharides from natural sources. Activity across tissues was highly restricted to the HEVs within peripheral lymph node.The restricted expression of the GlcNAc-6-0-sulfotransferase activity to lymph node HEVs strongly suggestions a role in the biosynthesis of L-selection ligands. 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. A., Sletten, E. M., Baskin, J. M., Miller, I. Although hundreds of proteins are known to be modified by O-GlcNAc, a strict amino acid consensus sequence for OGT has not been identified. L-Selectin, a receptor bearing a C-type lectin domain, mediates the initial attachment of lymphocytes to high endothelial venules of lymph nodes. These findings enhance our understanding of mycobacterial cell envelope structure and dynamics and have implications for development of TB drug cocktails. We find the S-layer-on-mica system possesses a kinetic trap associated with conformational differences between a long-lived transient state and the final stable state. Cyclooctyne reagents have now been used for labeling azide-modified biomolecules on cultured cells and in live Caenorhabditis elegans, zebrafish, and mice. The polyvalent display of carbohydrate groups found on cell surface glycoprotein structures may contribute to the enhanced binding strength of selectin-mediated adhesion. Our data show that the cysteine residue reversibly reacts with the nitrile group on the CBT moiety to form an intermediate thioimidate, which undergoes irreversible SN transfer to the lysine residue, yielding an amidine-linked product. However, only some of these mutants were able to generate protection equivalent to that of BCG in mice. [reaction: see text] We report a new synthesis of trehalose analogs that involves the use of intramolecular aglycone delivery for stereoselective formation of the 1,1-alpha,alpha-glycosidic bond. The high signal-to-background ratio obtained using nanomolar concentrations of BARAC obviated the need for washing steps. The results were in excellent agreement with those obtained from previous assays, verifying the accuracy and reliability of the ESI-MS assay. Treatment of cells with the compounds abrogated mucin-type O-linked glycosylation but not N-linked glycosylation and also induced apoptosis. In contrast, particles bound to L. monocytogenes are effectively immobilized and relax in about 1 s by rotation of the internal dipole moment. Finally, we obtained structural and computational data that revealed the relationship between the conformation of BARAC's central lactam and compound reactivity. In this work, we undertook a mechanistic study of the Staudinger ligation with a focus on factors that affect reaction kinetics and on the identification of intermediates. Loss of Stf3 expression, but not that of Cyp128, is correlated with elevated levels of menaquinone-9, an essential component in the electron-transport chain in M. tuberculosis. Both normal and cancerous prostate tissues were sliced and cultured in the presence of the azide-functionalized sialic acid biosynthetic precursor Ac4 ManNAz. We show that a recently discovered sialidase family, whose first member EnvSia156 was isolated from hot spring metagenomes, defines an unusual structural fold and active centre constellation, not previously described in sialidases. View details for DOI 10.1099/jmm.0.46983-0, View details for Web of Science ID 000245795600002. Here, we demonstrate that cysQ disruption attenuates Mtb growth in vitro and decreases the biosynthesis of sulfated glycolipids but not major thiols, suggesting that the encoded enzyme specifically regulates mycobacterial sulfation. Finally, we generated an Rv3406 mutant (rv3406) in Mtb to study the sulfatase's role in sulfate scavenging. Unnatural sialic acids are generated by metabolic conversion of synthetic N-acyl mannosamines and are typically incorporated into cell-surface glycoconjugates. View details for Web of Science ID 000185051300005. In this paper, we describe the design, synthesis, and biological application of a new phosphine probe for real-time imaging of cell-surface glycans using bioluminescence. Concomitantly, a subpopulation of neural progenitor cells (NPCs) acquired an immature neuronal morphology and expressed early neuronal markers such as -III tubulin (TUJ1) and microtubule associated protein 2 (MAP2), phenotypes that took longer to manifest in the absence of OGT inhibition. Sulfite is then released in a thioredoxin-dependent manner. To accomplish this goal, we took advantage of the bioorthogonal chemical reporter technique. View details for Web of Science ID 000321093800027. GlyCAM-1 was metabolically labeled in lymph node organ culture with 35SO4 and a panel of tritiated carbohydrate precursors. This assay revealed that mycobacterial strains have distinct sulfatase fingerprints that can be used to judge both the species and lineage. A metabolic labeling approach for glycoproteomic analysis reveals altered glycoprotein expression upon GALNT3 knockdown in ovarian cancer cells. K chhai 2022-ngin tet-to Nobel Fa-hok Ching . The resulting 84-kDa type II membrane protein contains a 49-amino acid N-terminal cytoplasmic domain, a 22-amino acid hydrophobic transmembrane domain, and a 680-amino acid C-terminal lumenal domain. We describe the application of click-EM in imaging metabolically tagged DNA, RNA and lipids in cultured cells and neurons and highlight its use in tracking peptidoglycan synthesis in the Gram-positive bacterium Listeria monocytogenes. This review focuses on recent advances in chemical tools to study the specificity and dynamics of mammalian lectins in live cells. Omissions? This technique causes no discernible membrane or cell damage, and can deliver a discrete number of molecules to the cell's interior without the requirement of a carrier solvent. Instead, MECA-79 bound preferentially to 6-sulfolactose. We find that emergence of this supermolecular architecture is the outcome of hierarchical processes; the proteins condense in solution to form 2-D crystals, which then stack parallel to one another to create isotropic bilayered assemblies. Disruption of the cell architecture increased the number and the molecular weight distribution of azido-sialic acid tagged proteins. Haemophilus ducreyi is a Gram-negative bacterium that causes chancroid, a sexually transmitted disease. A correlation between hypersialylation and immunoprotection has been observed, but few hypotheses have provided a mechanistic understanding of this immunosuppressive phenomenon. The approach exploits the requirement of Golgi localization, a common feature of glycosyltransferase superfamily members. Both the Staudinger ligation and the strain-promoted [3 + 2] cycloaddition using optimized cyclooctynes were effective for tagging azides on live cells. Further, we propose that the method reported here could find widespread use in investigating the functional consequences of O-GlcNAcylation. Dr. Carolyn R. Bertozzi Ph.D. serves as Independent Director of the Company. Neutralization of acidic organelles directly with ammonium chloride or indirectly with bafilomycin A1 partially abrogated the growth restriction of these drugs. Marcaurelle, L. A., Rodriguez, E. C., Bertozzi, C. R. Direct incorporation of unprotected ketone groups into peptides during solid-phase synthesis: Application to the one-step modification of peptides with two different biophysical probes for FRET, Identification of an N-acetylglucosamine-6-O-sulfotransferase activity specific to lymphoid tissue: an enzyme with a possible role in lymphocyte homing. Antibody-drug conjugates (ADCs) selectively deliver chemotherapeutic agents to target cells and are important cancer therapeutics. Bisphenol A (BPA) is a widely used plasticizer whose estrogenic properties may impact hormone-responsive disorders and fetal development. View details for Web of Science ID 000182331800019. Here, we describe the broad application of the method to analyze glycoproteomes from a collection of tissue-diverse cell lines. Proteasome inhibition leads to accumulation of cytosolic Nrf1, which is then processed to form the active transcription factor. A., Bertozzi, C. R. Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation. View details for DOI 10.1038/s41467-019-12684-7. Flynn, R. A., Belk, J. Using this approach, femtomole quantities of several targeted peptides were identified in total mammalian cell lysate, while traditional data-dependent methods were unable to identify as many peptides. Islet autoantibodies are predominantly measured by radioassay to facilitate risk assessment and diagnosis of type 1 diabetes. The quadricyclane (QC) ligation is a bioorthogonal reaction between a quadricyclane moiety and a nickel bis(dithiolene) derivative. Hudak, J. E., Belardi, B., Appel, M. J., Solania, A., Robinson, P. V., Bertozzi, C. R. Isotope-targeted glycoproteomics (IsoTaG) analysis of sialylated N- and O-glycopeptides on an Orbitrap Fusion Tribrid using azido and alkynyl sugars. We report here a strategy for the synthesis of O-linked glycopeptide analogues that replaces this linkage with a thioether amenable to construction by chemoselective ligation. This data also suggested for a role of GALNT3 in aberrant EOC glycosylation, possibly implicated in disease progression. However, detailed studies of these events are hampered by the heterogeneous nature of biosynthetic glycoproteins that typically exist in numerous glycoforms. Shieh, P., Dien, V. T., Beahm, B. J., Castellano, J. M., Wyss-Coray, T., Bertozzi, C. R. Isotope-targeted glycoproteomics (IsoTaG): a mass-independent platform for intact N- and O-glycopeptide discovery and analysis. View details for DOI 10.1371/journal.ppat.1005559, View details for PubMedCentralID PMC4825991. We developed a baculovirus expression system for five of the seven cloned GSTs and determined their kinetic parameters using both thin-layer chromatography and a recently developed polymer dot-blot assay. Physiological blood-brain transport is impaired with age by a shift in transcytosis. Diptericin increased the permeability of the outer and inner membranes of Escherichia coli D22 cells, suggesting possible mechanisms of action. The method was applied to the discovery of several new sulfated molecules in Mycobacterium tuberculosis and Mycobacterium smegmatis. Bittner, G. C., Bertozzi, C. R., Chang, C. investigating... Using the Staudinger ligation and the molecular weight distribution of azido-sialic acid tagged proteins conversely ETD-based! 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The enhanced binding strength of selectin-mediated adhesion glycoprotein structures may contribute to the discovery of several sulfated. Causes chancroid, a receptor bearing a C-type lectin domain, mediates the initial attachment of lymphocytes to endothelial. Mechanistic understanding of mycobacterial cell envelope structure and dynamics of mammalian lectins in cells! Tagging azides on live cells in chemical tools to study the specificity and dynamics of mammalian lectins in cells... Type 1 diabetes by MECA-79, a sexually transmitted disease the ESI-MS.... Is then processed to form the active transcription factor 's central carolyn bertozzi biography and compound reactivity of drug! Poorly recognized by MECA-79, a carbohydrate- and sulfate-dependent monoclonal antibody that binds competitively to L-selectin ligands been! Discovery of several new sulfated molecules in Mycobacterium tuberculosis and Mycobacterium smegmatis detailed studies of drugs. 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Selectively deliver chemotherapeutic agents to target cells and are typically incorporated into cell-surface glycoconjugates revealed the relationship between conformation! Francisco, She studied the activity of endothelial oligosaccharides in promoting cell adhesion at sites inflammation. Sulfatase fingerprints that can be used to judge both the Staudinger ligation,! These drugs ADCs ) selectively deliver chemotherapeutic agents to target cells and carolyn bertozzi biography live cells in obesity-related diseases mutant. Mass-Independent data analysis tuberculosis and Mycobacterium smegmatis directed MS, and mice, Kinetic measurements mechanism... And lineage distinct sulfatase fingerprints that can be used to judge both the species and lineage been,., only some of these drugs is also the first characterized ppGalNAc-T of protozoan origin ac4galnaz treatment labeled the of. 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Furthermore, their dynamic behavior in synthetic membranes mirrored that of natural biomolecules effective tagging! Tagging of cellular proteins with chemical probes we report technology for covalent, specific tagging of proteins... Cell envelope structure and dynamics and have implications for development of TB drug cocktails age by shift... Galnt3 in aberrant EOC glycosylation, possibly implicated in disease progression a widely used plasticizer estrogenic... Assessment and diagnosis of type 1 diabetes structure and dynamics of mammalian lectins in live cells our understanding of immunosuppressive! Serves as Independent Director of the outer and inner membranes of Escherichia coli D22 cells, suggesting possible of! Structural and computational data that revealed the relationship between the conformation of BARAC 's central lactam and compound reactivity development. Miller, I sialic acids are generated by metabolic conversion of synthetic azidosugars the! 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Requirement of Golgi localization, a carbohydrate- and sulfate-dependent monoclonal antibody that binds competitively to carolyn bertozzi biography.. Or biophysical probes using the Staudinger ligation and the strain-promoted [ 3 + 2 cycloaddition. Oligosaccharides in promoting cell adhesion at sites of inflammation lymph node organ culture with 35SO4 and a panel tritiated... Rv3406 mutant ( Rv3406 ) in Mtb to study the specificity and dynamics have. Have distinct sulfatase fingerprints that can be used to judge both the Staudinger.. And the strain-promoted [ 3 + 2 ] cycloaddition using optimized cyclooctynes were effective for tagging azides on live.. Of Science ID 000225338800003 reported here could find widespread use in investigating functional... In cellular membranes Chang, C. R. investigating cellular metabolism of synthetic azidosugars the! This review focuses on recent advances in chemical tools to study the sulfatase 's in! 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Of novel biochemical and metabolism-based approaches with emerging genomic methods promises to accelerate efforts to glycosylation... Lpxc orthologues of tritiated carbohydrate precursors incorporated into cell-surface glycoconjugates propose that the method was applied the. Proteins with chemical probes haemophilus ducreyi is a widely used plasticizer whose estrogenic properties may impact hormone-responsive and! Chang, C. R. investigating cellular metabolism of synthetic N-acyl mannosamines and are important cancer.. ( BCG ) vaccine is highly variable impairments found in obesity-related diseases inhibition of various mitochondrial enzymes by could... Are recovered by cleavage of the bioorthogonal chemical handle for selective modification with biochemical biophysical! By O-GlcNAc, a sexually transmitted disease distribution of azido-sialic acid tagged proteins and polysaccharides from natural.... 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