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. This system enables the production of glycoproteins that are functionalized for specific chemical modifications at their glycosylation sites. Regrettably, conventional biochemical and genetic methods often fall short for the study of glycans, because their structures are often not precisely defined at the genetic level. Such activatable probes with near-infrared (NIR) emission would be ideal for in vivo imaging but have proven difficult to engineer. We apply a pulsed magnetic field to align the magnetic dipole moments and use a high-transition temperature superconducting quantum interference device, an extremely sensitive detector of magnetic flux, to measure the magnetic relaxation signal when the field is turned off. These data are the first to suggest the feasibility of a strategy that improves the efficiency of gene transfer by using the biosynthetic machinery of the cell to engineer novel sugars on the cell surface. View details for DOI 10.1529/biophysj.107.125542, View details for Web of Science ID 000256231700017, View details for PubMedCentralID PMC2397374. N-Propanoylmannosamine (ManProp), which differs from ManBut by a single methylene group, did not inhibit PSA biosynthesis. Members of the Corynebacterineae, including Corynebacterium and Mycobacterium, have an atypical cell envelope characterized by an additional mycomembrane outside of the peptidoglycan layer. Robust surface mineral layers a few microns thick were obtained. To understand the adaptation of Mycobacterium tuberculosis to the intracellular environment, we used comprehensive metabolite profiling to identify the biochemical pathways utilized during growth on cholesterol, a critical carbon source during chronic infection. Chang, P. V., Prescher, J. Her father, William Bertozzi, was a physics professor at MIT. Treatment of cells with the compounds abrogated mucin-type O-linked glycosylation but not N-linked glycosylation and also induced apoptosis. These findings suggest that high mannose glycans are the major component of cell surface glycosylation with even terminal glucoses. Progress in understanding the biology of protein fatty acylation has been impeded by the lack of rapid direct detection and identification methods. There is growing interest in extending this progress to O-glycoproteomics, which necessitates comparisons of method performance for the two classes of glycopeptides. Hsiao, S. C., Shum, B. J., Onoe, H., Douglas, E. S., Gartner, Z. J., Mathies, R. A., Bertozzi, C. R., Francis, M. B. Elastomeric high-mineral content hydrogel-hydroxyapatite composites for orthopedic applications. The average overall agreement between ADAP and radioassay was above 91%. The compounds did not inhibit other mammalian glycosyltransferases or nucleotide sugar utilizing enzymes, suggesting selectivity for the ppGalNAcTs. WebCarolyn Ruth Bertozzi is an American chemist and Nobel laureate, known for her wide-ranging work spanning both chemistry and biology. Metabolic labeling can identify recently synthesized glycans and thus directly track glycan dynamics. An unnatural derivative of N-acetyl-mannosamine, which has a ketone group, was converted to the corresponding sialic acid and incorporated into cell surface oligosaccharides metabolically, resulting in the cell surface display of ketone groups. A microtiter plate assay for UDP-galactopyranose mutase, an essential cell wall biosynthetic enzyme of Mycobacterium tuberculosis, was developed. Charter, N. W., Mahal, L. K., Koshland, D. E., Bertozzi, C. R. Tyrosylprotein sulfotransferase inhibitors generated by combinatorial target-guided ligand assembly. Kiick, K. L., Saxon, E., Tirrell, D. A., Bertozzi, C. R. An inhibitor of the human UDP-GlcNAc 4-epimerase identified from a uridine-based library: A strategy to inhibit O-linked glycosylation, Homogeneous glycopeptides and glycoproteins for biological investigation. The sulfate esters on these structures are thought to be essential for high-affinity binding to L-selectin. Developmental events can be monitored at the cellular and molecular levels by using noninvasive imaging techniques. However, controlled investigations of the relationships between glycosylation, rigidity, and extension of membrane-bound mucins or similar macromolecules are lacking, largely because of the absence of tractable experimental models. We employed Tmp-SLF to modulate gene expression in a yeast three-hybrid assay. Here we applied the bioorthogonal chemical reporter technique for the molecular imaging of mucin-type O-glycans in live C. elegans. An essential step in this pathway is the activation of sulfate through adenylation by the enzyme ATP sulfurylase (ATPS), forming adenosine 5'-phosphosulfate (APS). However, current bioaerosol sampling approaches have reported low detection yields in sputum-positive TB cases. Welch Award in Chemistry (2022); The Dickson Prize in Medicine, University of Pittsburgh (2022); Dr H.P. Empty chamber samples were collected between patients as controls.The optimised RASC-2 protocol sampled a median of 258.4L (IQR: 226.9-273.6) of exhaled air per patient compared with 27.5L (IQR: 23.6-30.3) for RASC-1 (p<0.0001). 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. These tools have identified potential disease biomarkers and ways to monitor dynamic changes to the glycome in living organisms. A library of potential bisubstrate analogue inhibitors (1) targeting sulfotransferase enzymes was generated by the chemoselective ligation of the PAPS mimic 2 with a panel of 447 aldehydes. In this paper, we report on a general synthetic strategy for the assembly of glycopolymers that capitalizes on the intrinsic reactivity of reducing glycans toward hydrazides to form stable cyclic N-glycosides. Metabolically labeled glycoproteins are then tagged using Click chemistry and enriched with an isotopic recoding biotin probe. Conversely, ETD-based methods, especially EThcD, are indispensable for site-specific analyses of O-glycopeptides. After completing postdoctoral work at UCSF in the field of cellular immunology, she joined the UC Berkeley faculty in 1996. the glycome, has garnered significant attention from chemists and biologists alike. Seeliger, J. C., Holsclaw, C. M., Schelle, M. W., Botyanszki, Z., Gilmore, S. A., Tully, S. E., Niederweis, M., Cravatt, B. F., Leary, J. The emergence of drug-resistant Mycobacterium tuberculosis strains and the widespread occurrence of AIDS demand newer and more efficient control of tuberculosis. Here we report an approach toward generating homogeneously glycosylated proteins that involves chemical attachment of aminooxy glycans to recombinantly produced proteins via oxime linkages. Freeman, S. A., Goyette, J., Furuya, W., Woods, E. C., Bertozzi, C. R., Bergmeier, W., Hinz, B., van der Merwe, P. A., Das, R., Grinstein, S. Isotope Targeted Glycoproteomics (IsoTaG) to Characterize Intact, Metabolically Labeled Glycopeptides from Complex Proteomes. She grew up in Lexington, Massachusetts with two sisters, one of which is on the mathematics faculty at the University of California, Los Angeles (UCLA). In a proof-of-principle proteomics experiment, we used metabolic GalNAz labeling of human cells and a bioorthogonal chemical probe to affinity-purify and identify numerous O-GlcNAcylated proteins. Barb, A. W., Leavy, T. M., Robins, L. I., Guan, Z., Six, D. A., Zhou, P., Bertozzi, C. R., Raetz, C. R. Programmed assembly of 3-dimensional microtissues with defined cellular connectivity, Site-specific chemical modification of recombinant proteins produced in mammalian cells by using the genetically encoded aldehyde tag. Grogan, M. J., Kaizuka, Y., Conrad, R. M., Groves, J. T., Bertozzi, C. R. The chemistry and biology of mucin-type O-linked glycosylation, A conserved mechanism for sulfonucleotide reduction. This process involves two steps. 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. Collectively, these chemical approaches are contributing great insight into the myriad biological functions of oligosaccharides. A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems. This strategy will prove useful for both the identification of O-GlcNAc-modified proteins and the elucidation of the specific residues that bear this saccharide. Third, omega-alkynyl-myristate is specifically incorporated into endogenous co- and posttranslationally myristoylated proteins. The absence of activity on the trisaccharide Gal beta 1-->6Gal alpha-R indicates a requirement for a substrate with a terminal GlcNAc residue, suggesting that sulfation precedes further biosynthetic assembly of L-selection ligands. BT4244E575A derived from Bacteroides thetaiotaomicron is selective for truncated, asialylated core 1 structures commonly associated with malignant and premalignant tissues. Importantly, glycopolymers containing biologically relevant branched oligosaccharides, such as sialyl Lewis(x), as well as sulfated glycosaminoglycan-like epitopes can be readily prepared using our methodology. of Chemistry (2018); Foreign Member of the Royal Society Inductee (2018); National Inventors Hall of Fame Inductee (2017); Arthur C. Cope Award (2017); UCSF 150th Anniversary Alumni Excellence Award (2015); Hans Bloemendal Award (Radboud Univ. The leukocyte adhesion molecule L-selectin mediates lymphocyte homing to secondary lymphoid organs and to certain sites of inflammation. In 1961, Wittig and Krebs noted that the strained, cyclic alkyne cyclooctyne reacts violently when combined neat with phenyl azide, forming a triazole product by 1,3-dipolar cycloaddition. Winans, K. A., King, D. S., Rao, V. R., Bertozzi, C. R. Engineering novel cell surface receptors for virus-mediated gene transfer. Highly reactive cyclooctynes have been sought as substrates for Cu-free cycloaddition reactions with azides in biological systems. 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. The quadricyclane (QC) ligation is a bioorthogonal reaction between a quadricyclane moiety and a nickel bis(dithiolene) derivative. While several GPI-anchored proteins have been characterized, the biological functions of the GPI anchor have yet to be elucidated at a molecular level. This review focuses on recent advances in chemical tools to study the specificity and dynamics of mammalian lectins in live cells. Our results suggest a correlation between decreased alkyne bond angle and increased cyclooctyne reactivity. Furthermore, we developed a biomemetic coating strategy to interface BNNTs with proteins and cells. Our data show that O-glycopeptides cannot be robustly characterized with HCD-centric methods that are sufficient for N-glycopeptides, and glycoproteomic methods aiming to characterize O-glycopeptides must be constructed accordingly. The key building block, a pentasaccharide-Asn analogue containing two thiol residues, was incorporated into CD52 by 9-fluorenylmethoxycarbonyl (Fmoc)-based solid-phase peptide synthesis. Maturation is driven by the phosphoinositide kinase PIKfyve. To use IsoTaG, cell culture samples are metabolically labeled with an azido- or alkynyl-sugar. Mycobacterium tuberculosis synthesizes specific polyketide lipids that interact with the host and are required for virulence. This was confirmed by enzymatic assay of the partially purified enzyme with unnatural substrates. Here, we report a synergy between shape-generating processes in the cell interior and the external organization and composition of the cell-surface glycocalyx. Shon, D., Malaker, S. A., Pedram, K., Yang, E., Krishnan, V., Dorigo, O., Bertozzi, C. R. On-tissue microscale glycoproteomics and N-glycan imaging reveal global dysregulation of canine glioma glycoproteomic landscape. On the basis of these results, we propose possible pathways for 6-sulfo sialyl Lewis x biosynthesis and suggest that sulfation may be an early committed step. View details for Web of Science ID 000207584000003, View details for PubMedCentralID PMC138933. A preliminary study of the mechanism of this reaction, and refined conditions for its in vivo execution, are reported. and Irmgard Chu Distinguished Professorship in Chemistry (2005); Havinga Medal, Univ. Tian, E., Ten Hagen, K. G., SHUM, L., Hang, H. C., Imbert, Y., Young, W. W., Bertozzi, C. R., Tabak, L. A. The identification of certain cell surface oligosaccharides as potent antigens has prompted their use in tumor vaccines, and inspired new approaches to the management of tissue rejection subsequent to xenotransplantation. Indeed, we showed previously that the acylation of two mitochondrial proteins at their active site cysteine residues result in their inhibition. From 1996 to 2015, she was a professor of Chemistry Here, we report that metabolic cross-talk between the N-acetylgalactosamine salvage and O-GlcNAcylation pathways can be exploited for the tagging and identification of O-GlcNAcylated proteins. The reaction features a large dynamic range of reactivity, showcasing second-order rate constants as high as 2.310(3) M(-1) s(-1) using diboron reaction partners. This method for the selective formation of an amide bond, which does not require the orthogonal protection of distal functional groups, should find general utility in synthetic and biological chemistry. The unique labeling strategy of BCG by CDG-Tre provides a versatile tool for tracking Mtb in both pre- and post-phagocytosis and elucidating fundamental physiological and pathological processes related to the mycomembrane. We found that E. coli's FGE-like activity is similarly promiscuous, enabling the use of novel aldehyde tag sequences for in vivo modification of recombinant proteins. Riley, N. M., Bertozzi, C. R., Pitteri, S. J. View details for DOI 10.1016/S0166-6851(03)00196-8, View details for Web of Science ID 000185793400002. B., Shieh, P., Metruccio, M. E., Evans, D. J., Bertozzi, C. R., Fleiszig, S. J. The approach has applications in tissue-selective imaging of glycans for clinical and basic research purposes. One leads directly to the final low-energy state and the other to the kinetic trap. Metabolic labeling of recombinant interferon-beta and GlyCAM-Ig was achieved, demonstrating the utility of the method for functionalizing N-linked and O-linked glycoproteins of therapeutic interest. View details for DOI 10.1073/pnas.0403681101, View details for Web of Science ID 000225508400004, View details for PubMedCentralID PMC534710, View details for DOI 10.1074/jbc.M406397200, View details for Web of Science ID 000225229500103. View details for DOI 10.1016/j.molcel.2020.03.030. In this study we probed the importance of the stem region with respect to substrate preference, localization, and oligomerization. View details for Web of Science ID 000435537701267. Herein we report a semisynthetic method of producing membrane-anchored proteins. de Almeida, G., Townsend, L. C., Bertozzi, C. R. Mycobacterium tuberculosis Rv3406 Is a Type II Alkyl Sulfatase Capable of Sulfate Scavenging. Before joining Britannica in 2007, he worked at the University of Chicago Press on the Kara Rogers is the senior editor of biomedical sciences at Encyclopdia Britannica, where she oversees a range of content from medicine and genetics to microorganisms. Grabenstein, S., Barnard, K. N., Anim, M., Armoo, A., Weichert, W. S., Bertozzi, C. R., Parrish, C. R., Willand-Charnley, R. Systemic delivery of a targeted synthetic immunostimulant transforms the immune landscape for effective tumor regression. Despite its relevance in both health and disease, studies of the glycocalyx remain hampered by a paucity of methods to spatially classify its components. [27][46] The founding of Lycia Therapeutics occurred when Bertozzi's group discovered lysosome-targeting chimeras (LYTACs). The antibody-sialidase conjugate desialylated tumor cells in a HER2-dependent manner, reduced binding by natural killer (NK) cell inhibitory sialic acid-binding Ig-like lectin (Siglec) receptors, and enhanced binding to the NK-activating receptor natural killer group 2D (NKG2D). The cell-surface repertoire can be expanded to include abiotic functionality through the biosynthetic introduction of unnatural sugars into cellular glycans, a process termed metabolic oligosaccharide engineering. An intriguing example is Sulfolipid-1 (SL-1), a sulfated glycolipid that has been implicated in Mtb pathogenesis, although no direct role for SL-1 in virulence has been established. The assay method should be useful for inhibitor screens for both enzymes. View details for Web of Science ID 000180713000046. 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. Bruehl, R. E., Dasgupta, F., Katsumoto, T. R., Tan, J. H., Bertozzi, C. R., Spevak, W., Ahn, D. J., ROSEN, S. D., Nagy, J. O. Biosynthesis of L-selectin ligands: Sulfation of sialyl Lewis x-related oligosaccharides by a family of GlcNAc-6-sulfotransferases. The chemical reporter is then covalently modified in a highly selective fashion with an exogenously delivered probe. Lemieux, G. A., Yarema, K. J., Jacobs, C. L., Bertozzi, C. R. New directions in the synthesis of glycopeptide mimetics, Probing the surface structural rearrangement of hydrogels by sum-frequency generation spectroscopy. 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. Complementation of the mutant strain restored PAT production, demonstrating that PapA3 is essential for the biosynthesis of this glycolipid in vivo. Mauris, J., Mantelli, F., Woodward, A. M., Cao, Z., Bertozzi, C. R., Panjwani, N., Godula, K., Argueeso, P. Sulfatase-activated fluorophores for rapid discrimination of mycobacterial species and strains. Methods capable of directing orientation, as well as an understanding of the underlying physical mechanisms are, however, lacking. The structure reveals an unusual mode of cluster coordination by tandem cysteine residues and suggests how this arrangement might facilitate conformational change and cluster interaction with the substrate. Proteasome inhibition leads to accumulation of cytosolic Nrf1, which is then processed to form the active transcription factor. View details for Web of Science ID 000275864500006, View details for PubMedCentralID PMC2865253. Delaveris, C. S., Chiu, S. H., Riley, N. M., Bertozzi, C. R. The clinical impact of glycobiology: targeting selectins, Siglecs and mammalian glycans. Flynn, R. A., Pedram, K., Malaker, S. A., Batista, P. J., Smith, B. Here we studied the mechanism of sulfonucleotide reduction by APS reductase from the human pathogen Mycobacterium tuberculosis, using a combination of mass spectrometry and biochemical approaches. Investigations into the roles of protein glycosylation have revealed functions such as modulating protein structure and localization, cell-cell recognition, and signaling in multicellular systems. Rigidity and core glycosylation are therefore insufficient to ensure molecular projection outward from a membrane surface. The azide serves as a bioorthogonal chemical handle for selective modification with biochemical or biophysical probes using the Staudinger ligation. 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. Genomic and proteomic profiling form a basis for biological discovery. With their native proteinaceous backbones and natural glycosidic linkages, these agonists are attractive for translational applications. 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