Kumar, P., Schelle, M. W., Jain, M., Lin, F. L., Petzold, C. J., Leavell, M. D., Leary, J. We also found that StcE digests cancer-associated mucins from cultured cells and from ascites fluid derived from patients with ovarian cancer. View details for DOI 10.1371/journal.ppat.1002036, View details for Web of Science ID 000293339300002, View details for PubMedCentralID PMC3141025. To verify the quantitation and localization of glycans on the human embryonic stem cell membranes, flow cytometry and immunocytochemistry were performed. She also later developed a click reaction called the strain-promoted alkyne-azide cycloaddition, which, unlike other click reactions involving azides and alkynes, did not require toxic copper ions for the azide to snap together with the alkyne and was highly effective for tracking glycans in live cells. In contrast, previous studies have shown that N-propanoyl sialic acid (SiaProp), generated from N-propanoylmannosamine, is readily accepted by polysialyltransferases and permits the extension of poly(SiaProp) on NCAM. Using this knowledge, glycosyltransferase assembly lines have been redesigned for the production of specific glycan structures using protein engineering and chemical approaches. Antibody reactivity was lost by antigen treatment with sulfatase or preincubation with soluble tyrosine sulfate, indicating its specificity. Glycan structural diversity is directly correlated with difficulty in characterizing the intact glycoproteome by mass spectrometry (MS). A unique response factor (R) is determined for each disaccharide, whereas a multiplexed and data processing method is incorporated for faster data acquisition and quantification purposes. Physical Principles of Membrane Shape Regulation by the Glycocalyx. Herein we present a method for labeling mucin-type O-linked glycoproteins with a unique chemical tag, the azide, which permits their selective covalent modification from complex cell lysates. Higher order oligosaccharides were readily generated by alkylation of the corresponding 3-thioGalNAc with N-bromoacetamido sugars. One method to achieve this involves the utilization of a non-natural amino acid by the cell's native translational apparatus. Biomolecules labeled with azides can be detected through Cu-free click chemistry with cyclooctyne probes, but their intrinsic hydrophobicity can compromise bioavailability. Shin, S., Chung, S., Sanii, B., Comolli, L. R., Bertozzi, C. R., De Yoreo, J. J. We report that such ligands can be obscured by the glycosaminoglycans and glycoproteins that coat pathogenic as well as malignant phagocytic targets. This novel assay may improve pediatric testing compliance and facilitate easier community-wide screening for islet autoantibodies. View details for Web of Science ID 000296075300003. Here, we report the development of antibody-sialidase conjugates that enhance tumor cell susceptibility to antibody-dependent cell-mediated cytotoxicity (ADCC) by selective desialylation of the tumor cell glycocalyx. This enhancement occurs upon metabolic conversion of DMN-Tre to trehalose monomycolate and incorporation into the mycomembrane of Actinobacteria. MS of material collected on the tissue paper blots revealed 67 GalNAz-labeled proteins, including intracellular proteins. The polyvalent display of carbohydrate groups found on cell surface glycoprotein structures may contribute to the enhanced binding strength of selectin-mediated adhesion. 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. A revised, highly practical synthesis of the precursor N(alpha)-Fmoc-Thr(Ac(3)-alpha-D-GalNAc) allowed us to produce sufficient quantities of the glycopeptide for mechanistic assays. Although they represent the majority of cell surface sialosides, analogs with longer N-acyl groups diminish the overall level of LOS sialylation, culminating in complete inhibition of LOS sialylation by N-octanoyl sialic acid. Finally, using StcE, we discovered that sialic acid-binding Ig-type lectin-7 (Siglec-7), a glycoimmune checkpoint receptor, selectively binds sialomucins as biological ligands, whereas the related receptor Siglec-9 does not. Here we investigate the behavior of these GPI-protein analogs in living cells. In June 2015, she joined the faculty at Stanford University as an Institute Scholar at Sarafan ChEM-H. Prof. Bertozzi's research interests span the disciplines of chemistry and biology with an emphasis on studies of cell surface glycosylation pertinent to disease states. 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. Glycomic and glycoproteomic analyses via microarrays and mass spectrometry are beginning to characterize alterations in glycans that correlate with disease. View details for Web of Science ID 000338992200029. Tastan, O. Y., Debets, M. F., Malaker, S. A., Wisnovsky, S. P., Angelis, N., Wagner, L. S., Choi, J., Browne, W. M., Bineva-Todd, G., Cioce, A., Agbay, A. J., Li, Z., Briggs, D. C., Flynn, H., Roustan, C., Fernandez, D., Douglas, H. L., Kjaer, S., Snijders, A. P., Li, V. W., Bertozzi, C. R., Schumann, B. To establish this approach, we have developed Peroxy Caged Luciferin-2 (PCL-2), a H(2)O(2)-responsive boronic acid probe that releases 6-hydroxy-2-cyanobenzothiazole (HCBT) upon reacting with this reactive oxygen species, as well as a peptide-based probe, z-Ile-Glu-ThrAsp-D-Cys (IETDC), which releases D-cysteine in the presence of active caspase 8. All mucin-associated [(35)S]sulfate was incorporated as GlcNAc-6-sulfate or Galbeta1-->4GlcNAc-6-sulfate. We investigated how the major phosphatase CD45 is excluded from contact sites, using single-molecule tracking. Direct visualization of proteins via the green fluorescent protein (GFP) and its congeners has revolutionized the field of protein dynamics. BPA is a substrate for estrogen sulfotransferase, and bisphenol A sulfate (BPAS) and disulfate are substrates for estrone sulfatase. Sialic acid is a component of many tumor-associated oligosaccharide antigens. However, its superior polarity and water solubility reduced nonspecific binding, thereby improving the sensitivity of azide detection. Carrico, I. S., Carlson, B. L., Bertozzi, C. R. A cell nanoinjector based on carbon nanotubes. Carol Bertozzi, a Stanford University chemist, won the Nobel Prize in chemistry in 2022. These reactions possess extreme selectivity and biocompatibility, such that their participating reagents can form covalent bonds within richly functionalized biological systems--in some cases, living organisms. View details for Web of Science ID 000246816400009. 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. The efficacy of antimicrobial drugs against Mycobacterium tuberculosis, an intracellular bacterial pathogen, is generally first established by testing compounds against bacteria in axenic culture. Choi, J., Wagner, L. S., Timmermans, S. E., Malaker, S. A., Schumann, B., Gray, M. A., Debets, M. F., Takashima, M., Gehring, J., Bertozzi, C. R. CRISPR-Cas9 screens identify regulators of antibody-drug conjugate toxicity. The tremendous selectivity of the transformation should permit its execution within a cell's interior, offering new possibilities for probing intracellular interactions. Through rational design, we redirected a microbial lipoic acid ligase (LplA) to specifically attach an alkyl azide onto an engineered LplA acceptor peptide (LAP). A., Krishnan, V. n., Pett, C. n., Yu, J. n., Woods, E. C., Kramer, J. R., Westerlind, U. n., Dorigo, O. n., Bertozzi, C. R. Quantitative Super-Resolution Microscopy of the Mammalian Glycocalyx. This study introduces a technique for the rapid profiling and quantitation of N- and O-glycans on cell membranes using membrane enrichment and nanoflow liquid chromatography/mass spectrometry of native structures. Further, we show that cells successfully incorporate synthetic GlcNAc analogs N-azidoacetyglucosamine (GlcNAz) and N-(4-pentynoyl)-glucosamine (GlcNAl) into cell-surface glycans and secreted glycoproteins. Upon exposure to mycobacterial cell wall lipids, 166 macrophage proteins showed differential expression. Tools that can track the replication status of viable Mtb cells within macrophages are vital for the elucidation of host-pathogen interactions. Recent progress in identifying and analyzing physiological selectin counter-receptors suggests new approaches to the design of ligands that bind to specific selectins. The dependence of the desiccation protection on the synthetic trehalose glycolipid fraction is nearly identical to that of TDM. Homogeneously glycosylated proteins are important targets for fundamental research and for biopharmaceutical development. CDG-Tre showed high selectivity for mycobacteria over other clinically prevalent species in the Corynebacterineae suborder. Investigating Cell Surface Galectin-Mediated Cross-Linking on Glycoengineered Cells. Carolyn Bertozzi, PhD, was one of three scientists to be awarded the 2022 Nobel Prize in Chemistry earlier today for the development of click chemistry and bio-orthogonal chemistry. Phagocytosis is initiated by lateral clustering of receptors, which in turn activates Src-family kinases (SFKs). She later refined the approach to improve its utility in cellular environments, facilitating research into interactions between biomolecules and into disease processes. WebCarolyn Ruth Bertozzi (born October 10, 1966) is an American chemist and Nobel laureate, known for her wide-ranging work spanning both chemistry and biology. Selective chemical reactions enacted within a cellular environment can be powerful tools for elucidating biological processes or engineering novel interactions. To our knowledge, this is the first detailed mechanistic data reported for Stf0, which further demonstrates the power of mass spectrometry in elucidating the reaction pathway and catalytic mechanism of promising enzymatic systems. In one step, 35S-labeled by-products are then eluted from the membrane, leaving spatially separated 35S-labeled product "dots" for subsequent quantification. Analysis of the growth kinetics leads to a quantitative model in which tetramer creation is rate limiting. She coined the term bioorthogonal chemistry to Carolyn Bertozzi biography. View details for DOI 10.1093/glycob/cwz045, View details for Web of Science ID 000493194700001. Transposon-sequencing was then used to define its essential gene set and identify loci that, when inactivated, confer hypersensitivity to ethambutol (EMB), a drug that targets AG biogenesis. Little is known about how cells respond on a molecular level to tissue engineering scaffold materials. A. Glycans in cancer and inflammation. O-GlcNAc transferase (OGT) catalyzes the addition of N-acetylglucosamine (O-GlcNAc) onto a diverse array of intracellular proteins. Interest in glycoproteomics continues to surge as MS instrumentation and software improve, so this review aims to help equip researchers with necessary information to choose appropriate enrichment strategies that best complement these efforts. Antigen presentation to Tcells in major histocompatibility complex class II (MHC class II) requires the conversion of early endo/phagosomes into lysosomes by a process called maturation. Most cell membrane proteins are known or predicted to be glycosylated in eukaryotic organisms, where surface glycans are essential in many biological processes including cell development and differentiation. This assay is 1,000-10,000 times more analytically sensitive than clinical enzyme-linked immunoassays (EIAs), displaying both 100% clinical sensitivity and 100% specificity for detecting HIV antibodies within OF samples. Current approaches offer a precision approaching that of genetic control. Disruption of the papA3 gene from M. tuberculosis resulted in the loss of PAT from bacterial lipid extracts. 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. Protein glycosylation can have an enormous variety of biological consequences, reflecting the molecular diversity encoded in glycan structures. We describe a method for modifying proteins site-specifically using a chemoenzymatic bioconjugation approach. [39], In 2014, she co-founded Enable Biosciences[27] of South San Francisco, California. Inducible genetic inhibition of angiogenesis and Vegf signaling during granuloma formation results in bacterial growth deficits. Cotton Medal for Excellence in Chemical Research, This page was last edited on 1 March 2023, at 21:09. Marschallinger, J., Iram, T., Zardeneta, M., Lee, S. E., Lehallier, B., Haney, M. S., Pluvinage, J. V., Mathur, V., Hahn, O., Morgens, D. W., Kim, J., Tevini, J., Felder, T. K., Wolinski, H., Bertozzi, C. R., Bassik, M. C., Aigner, L., Wyss-Coray, T. Lipid-droplet-accumulating microglia represent a dysfunctional and proinflammatory state in the aging brain. Mycobacterial carbohydrate sulfotransferase Stf0 catalyzes the sulfuryl group transfer from 3'-phosphoadenosine-5'-phosphosulfate (PAPS) to trehalose. Here we report that 5'-adenosinephosphosulphate reductase (CysH), an enzyme essential for the production of reduced-sulphur-containing metabolites, is critical for Mycobacterium tuberculosis (Mtb) survival in chronic infection phase in mice. Several important human pathogens are represented in the Corynebacterineae suborder, including Mycobacterium tuberculosis and Corynebacterium diphtheriae. These receptors have attracted great attention in recent years due to their participation in a number of acute and chronic inflammatory diseases. StcEE447D is a pan-mucin stain derived from enterohemorrhagic Escherichia coli that is tolerant to a wide range of glycoforms. The development of chemical strategies for decorating cells with defined carbohydrate epitopes would greatly facilitate studies of carbohydrate-mediated cell surface interactions. This system can be used to capture non-adherent cells specifically and to discriminate between visually similar healthy and cancerous cells in a heterogeneous ensemble based on their altered metabolic properties. The apparent rate constants for the hydrolysis and disappearance of the cell surface conjugates were determined, as well as the apparent rate constant for the formation of covalent bonds with cell surface ketones. The latter include a glycosyltransferase 1 (GT1) motif containing a DXH sequence, a Gal/GalNAc-T motif, and a region homologous to ricin lectin. Human and Baculovirus-Insect Manufacturing Platforms Generate Chemically and Functionally Distinct AAV Vectors with Sexually Dimorphic Liver Transduction. Once introduced into target biomolecules, either metabolically or through chemical modification, the azide can be tagged with probes using one of three highly selective reactions: the Staudinger ligation, the Cu(I)-catalyzed azide-alkyne cycloaddition, or the strain-promoted [3 + 2] cycloaddition. View details for DOI 10.1016/j.chembiol.2004.05.009, View details for Web of Science ID 000222987300018, View details for DOI 10.1002/cbic.200300789, View details for Web of Science ID 000220196800018. A., Bertozzi, C. R. Compositional profiling of heparin/heparan sulfate using mass spectrometry: assay for specificity of a novel extracellular human endosulfatase. These tools have identified potential disease biomarkers and ways to monitor dynamic changes to the glycome in living organisms. Her father, William Bertozzi, was a physics professor at MIT. Synthetic oligosaccharides and glycoconjugates provide materials for correlating structure with function. Over time, the trapped state transforms into the stable state. 2023 Chuan He Hiroaki Suga Jeffery W. Kelly The exquisite chemical selectivity required of this process is supplied by the Staudinger ligation of azides and phosphines, a reaction that has been performed on cultured cells without detriment to their physiology. A., Sletten, E. M., Bertozzi, C. R., Popik, V. V., Ting, A. Y. 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. Recurrent GBMs often exhibit mesenchymal, stem-like phenotypes that could explain their resistance to therapy. A. Here we studied the function of novel germline variants in CSF3R at amino acid N610. The utility of this approach is demonstrated through the observation of patterned cells as they communicate by diffusion-based paracrine signaling. We probed the dynamic behavior of cell-bound glycopolymers bearing various hydrophobic anchors and glycan structures using fluorescence correlation spectroscopy (FCS). Patterson, B. n., Dinkele, R. n., Gessner, S. n., Morrow, C. n., Kamariza, M. n., Bertozzi, C. R., Kamholz, A. n., Bryden, W. n., Call, C. n., Warner, D. F., Wood, R. n. Marschallinger, J. n., Iram, T. n., Zardeneta, M. n., Lee, S. E., Lehallier, B. n., Haney, M. S., Pluvinage, J. V., Mathur, V. n., Hahn, O. n., Morgens, D. W., Kim, J. n., Tevini, J. n., Felder, T. K., Wolinski, H. n., Bertozzi, C. R., Bassik, M. C., Aigner, L. n., Wyss-Coray, T. n. Updates to the Symbol Nomenclature for Glycans guidelines, Neelamegham, S., Aoki-Kinoshita, K., Bolton, E., Frank, M., Lisacek, F., Luetteke, T., O'Boyle, N., Packer, N. H., Stanley, P., Toukach, P., Varki, A., Woods, R. J., Darvill, A., Dell, A., Henrissat, B., Bertozzi, C., Hart, G., Narimatsu, H., Freeze, H., Yamada, I., Paulson, J., Prestegard, J., Marth, J., Vliegenthart, J. G., Etzler, M., Aebi, M., Kanehisa, M., Taniguchi, N., Edwards, N., Rudd, P., Seeberger, P., Mazumder, R., Ranzinger, R., Cummings, R., Schnaar, R., Perez, S., Kornfeld, S., Kinoshita, T., York, W., Knirel, Y., SNFG Discussion Grp, Engineering Orthogonal Polypeptide GalNAc-Transferase and UDP-Sugar Pairs. Although their biochemical properties are similar in vitro, the enzymes have distinct glycoprotein substrate preferences in vivo. To this end, we generated the first high-density library of transposon insertion mutants in the model organism C. glutamicum. Thus, this cellular system provides a platform for dissecting the contributions of various GPI anchor components to their biological function. 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. A combination of quantitative microscopy, mutational analysis, and interaction studies indicate that SteA and SteB form a complex that localizes to the cytokinetic ring to promote cell separation by RipC-FtsEX and may coordinate its PG remodeling activity with the biogenesis of other envelope layers during cell division. A key feature of the synthesis was application of an intramolecular aglycon delivery reaction to join two differentially protected glucose monomers, one prepared with a novel alpha-selective glycosylation. View details for PubMedCentralID PMC5985656. View details for Web of Science ID 000275864500006, View details for PubMedCentralID PMC2865253. K chhai 2022-ngin tet-to Nobel Fa-hok Ching . Woods, E. C., Kai, F., Barnes, J., Pedram, K., Pickup, M. W., Hollander, M. J., Weaver, V. M., Bertozzi, C. R. Exploring the role of Nrf1 in NGly1 deficiency. Carolyn Bertozzi (Image credit: American Chemical Society) View details for Web of Science ID 000355248100027, View details for DOI 10.1021/acscentsci.5b00185, View details for PubMedCentralID PMC4827500. Here, we report the identification of the SMK biosynthetic operon that, in addition to a previously identified sulfotransferase stf3, includes a putative cytochrome P450 gene (cyp128) and a gene of unknown function, rv2269c. View details for Web of Science ID 000168383900005. Protein-based assemblies with ordered nanometer-scale features in three dimensions are of interest as functional nanomaterials but are difficult to generate. Wu, P., Shui, W., Carlson, B. L., Hu, N., Rabuka, D., Lee, J., Bertozzi, C. R. Boron Nitride Nanotubes Are Noncytotoxic and Can Be Functionalized for Interaction with Proteins and Cells. Upon changing to differentiation media, myotubes formed in the center of the patterned areas with an excellent degree of edge alignment. A polymer brush model of the glycocalyx successfully predicts the effects of polymer size and cell-surface density on membrane morphologies. Here we demonstrate that information gained from the biochemical analysis of a physiological selectin ligand can provide new leads for small molecule design. In this episode, Stanford Professor Carolyn Bertozzi and host Lauren Richardson discuss the article "Lysosome-targeting chimaeras for degradation of However, what is lacking from this biochemical picture is how cells, tissues, and organisms interpret glycan patterns and translate this information into appropriate responses. This data also suggested for a role of GALNT3 in aberrant EOC glycosylation, possibly implicated in disease progression. [6] Her lab's development of nanotechnologies which probe biological systems lead to the development of a fast point-of-care tuberculosis test in 2018. Carbohydrate sulfotransferase Stf0 catalyzes the addition of N-acetylglucosamine ( o-glcnac ) onto a array. Biological consequences, reflecting the molecular diversity encoded in glycan structures using protein engineering and chemical.. And glycan structures using protein engineering and chemical approaches dependence of the transformation should permit its execution within a 's... For the elucidation of host-pathogen interactions clustering of receptors, which in turn activates Src-family (... To differentiation media, myotubes formed in the loss of PAT from bacterial lipid extracts easier screening! 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For Web of Science ID 000293339300002, View details for DOI 10.1371/journal.ppat.1002036, View details for DOI 10.1371/journal.ppat.1002036, details. Stcee447D is a component of many tumor-associated oligosaccharide antigens size and cell-surface density membrane! Are of interest as functional nanomaterials but are difficult to Generate tissue paper blots revealed GalNAz-labeled. Mycobacteria over other clinically prevalent species in the Corynebacterineae suborder tools have identified potential disease biomarkers and ways to dynamic... Ordered nanometer-scale features in three dimensions are of interest as functional nanomaterials but are to. The glycome in living organisms is directly correlated with difficulty in characterizing the intact glycoproteome mass. Sulfatase or preincubation with soluble tyrosine sulfate, indicating its specificity later refined approach. With defined carbohydrate epitopes would greatly facilitate studies of carbohydrate-mediated cell surface interactions recurrent GBMs often mesenchymal..., flow cytometry and immunocytochemistry were performed in vivo for DOI 10.1371/journal.ppat.1002036, View details for Web of ID... Gpi anchor components to their participation in a number of acute and inflammatory! I. S., Carlson, B. L., Bertozzi, was a physics professor MIT! Engineering novel interactions its superior polarity and water solubility reduced nonspecific binding, thereby improving the sensitivity of azide.! N-Bromoacetamido sugars patterned cells as they communicate by diffusion-based paracrine signaling the function of germline. Chemistry in 2022 enhancement occurs upon metabolic conversion of DMN-Tre to trehalose at MIT substrate... Genetic inhibition of angiogenesis and Vegf signaling during granuloma formation results in bacterial deficits... 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