Fluorescent bioorthogonal smart probes across the visible spectrum will enable sensitive visualization of metabolically labeled molecules in biological systems. Applying IsoStamp, we were able to detect femtomole quantities of a single tagged protein from total mammalian cell lysates at signal-to-noise ratios as low as 2.5:1. Synthetic glycopolymers that emulate cell-surface mucins have been used to elucidate the role of mucin overexpression in cancer. Here, we engineer living cells to tag glycans with editable chemical functionalities while providing information on biosynthesis, physiological context, and glycan fine structure. [6] In 1999, while working with HHMI and at Berkeley, she founded the field of bioorthogonal chemistry and coined the term in 2003. Metastasis depends upon cancer cell growth and survival within the metastatic niche. The importance of sulfated molecules in cell-cell communication motivated us to develop a rapid two-step method for identifying these metabolites in microorganisms, particularly in pathogenic mycobacteria. The 35S-labeled products are then captured on an appropriate membrane, taking advantage of their polymeric architecture. To accomplish this goal, we took advantage of the bioorthogonal chemical reporter technique. Though not directly subject to mutation, we can determine glycan structure-function relationships by synthesizing defined glycoconjugates or by altering natural glycosylation pathways. 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. Proof of principle was performed by using various heparin/HS samples isolated from bovine and porcine tissues. A., Bertozzi, C. R. Cell type-selective secretome profiling in vivo. In an effort to mimic the high-affinity binding, polyvalent scaffolds that contain multicomponent displays of selectin-binding ligands have been synthesized. WebAn important step is to identify the key go/nogo experiments that would" - Carolyn Bertozzi (@CarolynBertozzi) - Prof @Stanford & Bioorthogonal Chemistry Pioneer Shoutout: @EnableBio, @Palleon_Pharma, @vennbio, @OliluxB, @gracescience, @LyciaTx, @NobelPrize! Douglas, E. S., Hsiao, S. C., Onoe, H., Bertozzi, C. R., Francis, M. B., Mathies, R. A. Synthesis and Microcontact Printing of Dual End-Functionalized Mucin-like Glycopolymers for Microarray Applications. Bertozzi, C. R., SINGER, M. S., ROSEN, S. D. L-selectin-carbohydrate interactions: Relevant modifications of the Lewis x trisaccharide. Mockl, L., Pedram, K., Roy, A., Krishnan, V., Gustavsson, A., Dorigo, O., Bertozzi, C., Moerner, W. Enzyme toolkit for selective enrichment and analysis of mucin-domain glycoproteins. View details for Web of Science ID 000082564500003. Investigation of their function has been greatly assisted by sources of homogeneous material. Progress in understanding the biology of protein fatty acylation has been impeded by the lack of rapid direct detection and identification methods. SiaNAz was found to comprise between 4% and 41% of total sialosides, depending on the system. A., Bertozzi, C. R. Fluorophore Targeting to Cellular Proteins via Enzyme-Mediated Azide Ligation and Strain-Promoted Cycloaddition. View details for Web of Science ID 000233068900026, View details for Web of Science ID 000234130500004. Chem. This review highlights changes in glycosylation associated with cancer and chronic inflammation and new therapeutic and diagnostic strategies that are based on the underlying glycobiology. 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. Application of our enzymatic toolkit to ascites fluid and tissue slices from patients with ovarian cancer facilitated characterization of patients based on differences in mucin cleavage and expression patterns. Understanding the impact of a scaffold on attached cells will facilitate the design of improved tissue engineering materials. A., Bertozzi, C. R. Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation. Here, we demonstrate that the conserved N-acetyglucosamine (GlcNAc) residues within chitobiose cores of N-glycans in the model organism Saccharomyces cerevisiae can be specifically targeted for metabolic replacement by unnatural sugars. Incorporation of sialosides into LOS was assessed by matrix-assisted laser desorption and electrospray ionization mass spectrometry. We show that both Rv1129c and the MCC enzymes are required for intracellular growth in macrophages and that the growth defect of MCC mutants is largely attributable to the degradation of host-derived cholesterol. A combination of PZA and the {Au(PPh3)}-thiol polymeric species appears to lead to enhanced efficacy of 1 against M. tuberculosis. Traditional spectrophotometric assays are not applicable to the NodST system since no shift in absorption accompanies sulfuryl group transfer. These included proteins involved in the immune response, oxidation and reduction, and vesicle transport, as well as other cellular processes. Their large size and extensive glycosylation makes the synthesis of these biopolymers impractical. [43], In 2017, Bertozzi helped found InterVenn Biosciences, which uses mass spectrometry and artificial intelligence to enhance glycoproteomics for target and biomarker discovery, ovarian cancer diagnostics, and predicting the successes and failures of clinical trials. Palmitoylation is a widespread, reversible lipid modification that has been implicated in regulating a variety of cellular processes. Specific labeling of biomolecules with biochemical and biophysical probes is a central element of proteomics research. Using this method, we identified 21 putative palmitoylated proteins in the rat liver mitochondrial matrix, a compartment not recognized for its content in palmitoylated proteins, and confirmed the palmitoylation of newly identified mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase. Stanford is continually monitoring the status of COVID-19, also called novel coronavirus. Varki, A., Cummings, R. D., Aebi, M., Packer, N. H., Seeberger, P. H., Esko, J. D., Stanley, P., Hart, G., Darvill, A., Kinoshita, T., Prestegard, J. J., Schnaar, R. L., Freeze, H. H., Marth, J. D., Bertozzi, C. R., Etzler, M. E., Frank, M., Vliegenthart, J. F., Ltteke, T., Perez, S., Bolton, E., Rudd, P., Paulson, J., Kanehisa, M., Toukach, P., Aoki-Kinoshita, K. F., Dell, A., Narimatsu, H., York, W., Taniguchi, N., Kornfeld, S. Chemistry Is Central to Repairing Genes and Global Health: Reflections on the 2015 Nobel Prizes in Chemistry and Physiology or Medicine. Sletten, E. M., Nakamura, H., Jewett, J. C., Bertozzi, C. R. Synthesis of Glycopolymers for Microarray Applications via Ligation of Reducing Sugars to a Poly(acryloyl hydrazide) Scaffold, A Strategy for the Selective Imaging of Glycans Using Caged Metabolic Precursors. Methods for directing the cell surface expression of novel protein-based and oligosaccharide-based epitopes are stimulating new directions in biotechnology and biomedical research. Although experiments with organisms in vitro have yielded a wealth of information on PG synthesis and maturation, it is unclear how these studies translate to bacteria replicating within host cells. DMN-Tre labeling was detected within minutes and was inhibited by heat killing of mycobacteria. View details for Web of Science ID 000172448800001. The approach provides a means for studying sulfate-dependent processes in cellular systems and, potentially, in vivo. [17][18] While at Berkeley, she discovered that viruses can bind to sugars in the body. 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. Muia, R. P., Yu, H., Prescher, J. These techniques have permitted the study of molecular components within the context of living cells. WebProfessor 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. Chemical inducers of dimerization (CIDs) are cell-permeable small molecules capable of dimerizing two protein targets. Cortez, F. d., Gebhart, D., Robinson, P. V., Seftel, D., Pourmandi, N., Owyoung, J., Bertozzi, C. R., Wilson, D. M., Maahs, D. M., Buckingham, B. 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. 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. Tumors which remodel their glycocalyces, by overexpressing bulky glycoproteins like mucins, exhibit a higher predisposition to metastasize, but the role of mucins in oncogenesis remains poorly understood. Kinetic analysis of the mutants identified residues that are essential for catalytic activity. The repertoire of sialic acids presented by cells can be expanded to include unnatural variants by intercepting the sialic acid biosynthetic pathway with unnatural precursors. Bertozzi is a professor Modification of the terminal arabinan residues of this lipoglycan with mannose caps in M. tuberculosis or with phosphoinositol caps in Mycobacterium smegmatis results in distinct host immune responses. Specific glycocalyx compositions can also induce plasma membrane instabilities to generate more exotic undulating and pearled membrane structures and drive secretion of extracellular vesicles. Our results demonstrate a key role of PIKfyve in the processing and presentation of antigens, which should be taken into consideration when targeting PIKfyve in autoimmune disease and cancer. A significant proportion (>45%) of the identified O-GlcNAc sites lie in close proximity to or coincide with a known phosphorylation site, supporting the potential for PTM crosstalk. For example, cancer cells frequently display glycans at different levels or with fundamentally different structures than those observed on normal cells. Positioned at the C-terminus of many eukaryotic proteins, the glycosylphosphatidylinositol (GPI) anchor is a posttranslational modification that anchors the modified protein in the outer leaflet of the cell membrane. Most clinically approved biomarkers of cancer are glycoproteins, and those residing on the cell surface are of particular interest in biotherapeutics. To overcome this barrier, we developed an artificial receptor based on expression of a novel sugar. Given that M. tuberculosis typically persists in the phagosomal vacuole after being phagocytosed by macrophages, we performed a proteomic analysis of that organelle after treatment of macrophages with LAMs purified from the two mycobacterial species. Conceptual translation of the cDNA sequence reveals a relatively long (i.e. The human pathogen Mycobacterium tuberculosis (M. tb) is thought to control the human immune response with diverse biomolecules, including a variety of exotic lipids. They also suggest increased P. aeruginosa adhesion to MyD88-/- and blotted corneas is not due to reduction in total surface glycosylation, and for tissue paper blotting is likely due to cell permeabilization.-Jolly, A. L., Agarwal, P., Metruccio, M. M. E., Spiciarich, D. R., Evans, D. J., Bertozzi, C. R., Fleiszig, S. M. J. Corneal surface glycosylation is modulated by IL-1R and Pseudomonas aeruginosa challenge but is insufficient for inhibiting bacterial binding. Here we present a unified design, based on the principle of photoinduced electron transfer, to access a panel of highly fluorogenic azide probes that are activated by conversion to the corresponding triazoles via click chemistry. CholA-anchored glycopolymers therefore expand the application of glycocalyx engineering in glycobiology. The recently described O-glycoprotease OpeRATOR presents exciting opportunities for O-glycoproteomics. Although several proteins involved in SL-1 biosynthesis have been identified, the enzymes that acylate the T2S core to form SL(1278) and SL-1, and the biosynthetic order of these acylation reactions, are unknown. [38] Redwood Bioscience is a biotechnology company that uses SMARTag, a site-specific protein modification technology that allows small drugs to attach to sites on the proteins and can be used to help fight cancers. [27], Bertozzi also previously served on the research advisory board of several pharmaceutical companies including GlaxoSmithKline, and until recently Eli Lilly.[48]. Recent progress in identifying and analyzing physiological selectin counter-receptors suggests new approaches to the design of ligands that bind to specific selectins. WebIn the early 1990s, Carolyn Bertozzi began mapping a glycan that attracts immune cells to lymph nodes. Applications to noninvasive imaging and glycoproteomic analyses are discussed. By analyzing the time and temperature dependencies of formation and transformation we find that the energy barriers to formation of the two states differ by only 0.7 kT, but once the high-energy state forms, the barrier to transformation to the low-energy state is 25 kT. In the ligation reaction, the intermediate aza-ylide undergoes intramolecular reaction with an ester, forming an amide bond faster than aza-ylide hydrolysis would otherwise occur in water. Tests against related enzymes confirmed the compound's specificity for the UDP-GlcNAc 4-epimerase. Methods for targeting of small molecules to cellular proteins can allow imaging with fluorophores that are smaller, brighter, and more photostable than fluorescent proteins. Inhibitors of carbohydrate recognition and biosynthesis can reveal the biological functions of the carbohydrate epitope and its cognate receptors. However, for targeting of hydrophobic fluorophores such as ATTO 647N, the hydrophobicity of ADIBO was detrimental, and superior targeting was achieved by conjugation to the less hydrophobic monofluorinated cyclooctyne (MOFO). [10][11], Bertozzi was awarded the 2022 Nobel Prize in Chemistry, jointly with Morten P. Meldal and Karl Barry Sharpless, "for the development of click chemistry and bioorthogonal chemistry". 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. 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. Monomeric sialyl Lewis(X) (sLe(x)) and sLe(x)-like oligosaccharides are minimal structures capable of supporting selectin binding in vitro. The group was deliberately composed not only of individuals with a current research emphasis in the glycosciences, but also of many experts from other fields, who evinced a strong interest in being involved in the discussions. This type of enzyme catalyzes the initial step of mucin-type O-glycosylation, that is, the transfer of GalNAc in O-glycosidic linkage to serine and threonine residues in polypeptides. Dai, T. n., Xie, J. n., Zhu, Q. n., Kamariza, M. n., Jiang, K. n., Bertozzi, C. R., Rao, J. n. Optimal Dissociation Methods Differ for N- and O-glycopeptides. After completing postdoctoral work at UCSF in the field of cellular immunology, she joined the UC Berkeley faculty in 1996. These alkenyl compounds arise from a hydrogen transfer reaction from solvent to the unisolable intermediate, and we postulate that the reaction proceeds via a radical mechanism originating from the strained alkynyl bond that has unusually high radical character. In this report, we screened FGEs from M. tuberculosis and S. coelicolor against synthetic peptide libraries and identified new substrate sequences that diverge from the canonical motif. Here, we demonstrate that, relative to wild-type controls, ST8Sia IV(-/-) mice have a 30% reduction in total thymocytes and a concomitant deficiency in the earliest thymocyte precursors. General overview of non-natural amino acid incorporation into a protein.a) Difference between normal translation (1), translation in the absence of nnAA (2) and when nnAA is supplied (3).b) The orthogonal tRNA can only work with the orthogonal aminoacyl-tRNA (aaRS) synthetase and the engineered tRNA with the engineered aaRS. This study reports the vaccine potential of an attenuated 5'-adenosine phosphosulfate reductase mutant (DeltacysH) of M. tuberculosis. Together with previous studies, these findings suggest that this redox cofactor may play a role in mycobacterial pathogenesis. The properties of therapeutic proteins can be enhanced by chemical modification. Monomeric and multivalent oligosaccharides that bind to bacterial and viral receptors have been shown to abrogate infection by agents such as Helicobacter pilori, influenza virus and HIV. The data suggest that the ppGalNAcTs can be classified into at least four types, which working together, are able to produce densely glycosylated mucin glycoproteins. CDG-Tre fluoresces upon activation by BlaC, the -lactamase uniquely expressed by Mtb, and the fluorescent product is subsequently incorporated within the bacterial cell wall via trehalose metabolic pathway. We developed a sulfatase-activated probe, 7-hydroxy-9H-(1,3-dichloro-9,9-dimethylacridin-2-one)-sulfate, that detects enzyme activity in native protein gels, allowing the rapid detection of sulfatases in mycobacterial lysates. We frame central issues regarding determination of protein-level variation and PTMs, including some paradoxes present in the field today. Here, we present a panel of bacterial proteases that cleave mucin domains via distinct peptide- and glycan-based motifs, generating a diverse enzymatic toolkit for mucin-selective proteolysis. Her research group profiles changes in cell surface glycosylation associated with cancer, inflammation and bacterial infection, and uses this information to develop new The ability to rapidly and systematically vary the composition of these assemblies is a distinguishing feature of this methodology and may be applied to the study of other systems where composite binding determinants are important for high-affinity binding. Here we report a new biocompatible CID, Tmp-SLF, which dimerizes E. coli DHFR and FKBP and has no endogenous mammalian targets that would lead to unwanted in vivo side effects. 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