Sensitive detection of multiple islet autoantibodies in type 1 diabetes using small sample volumes by agglutination-PCR. Hatzios, S. K., Iavarone, A. T., Bertozzi, C. R. Noncovalent cell surface engineering: Incorporation of bioactive synthetic glycopolymers into cellular membranes. The importance and complexity associated with the totality of glycan structures, i.e. Because a sulfur auxotrophic strain is the only requirement of the approach, many microorganisms can be studied in this manner. The system was used to induce and repress heterologous protein overexpression reversibly, to create a conditional gene knockdown, and to control gene expression in a macrophage infection model. Thus, sialylation of H. ducreyi LOS can be modulated with respect to the structure of the terminal sialic acid residue and the extent to which the LOS acceptor is modified by supplying the bacteria with various sialic acid analogs. Detection and quantification of fatty acid fluxes in animal model systems following physiological, pathological, or pharmacological challenges is key to our understanding of complex metabolic networks as these macronutrients also activate transcription factors and modulate signaling cascades including insulin sensitivity. A panel of analogues with ketone-containing N-acyl groups that varied in the length or steric bulk was chemically synthesized and tested for metabolic conversion to cell surface glycans. The assay was validated by measuring K(M) values for PAPS and K(I) values for PAP, the product of sulfuryl transfer. These studies establish Cu-free click chemistry as a bioorthogonal reaction that can be executed in the physiologically relevant context of a mouse. cis-Cyclopropanation of mycobacterial mycolic acids by pcaA drives the activation of host Vegf signaling within granuloma macrophages. In particular, Bertozzi has advanced the understanding of cell surface oligosaccharides involved in cell recognition and inter-cellular communication. The cysH mutant was also susceptible to peroxynitrite and hydrogen peroxide in vitro. Third, omega-alkynyl-myristate is specifically incorporated into endogenous co- and posttranslationally myristoylated proteins. Here we review common enrichment strategies used in modern mass spectrometry-based glycoproteomic experiments, including lectins and other affinity chromatographies, hydrophilic interaction chromatography and its derivatives, porous graphitic carbon, reversible and irreversible chemical coupling strategies, and chemical biology tools that often leverage bioorthogonal handles. The approach was validated by metabolic labeling of nuclear pore protein p62, which is known to be posttranslationally modified with O-GlcNAc. Indeed, we showed previously that the acylation of two mitochondrial proteins at their active site cysteine residues result in their inhibition. Here we explored their effect on corneal surface glycosylation using a metabolic label, tetra-acetylated N-azidoacetylgalactosamine (Ac4GalNAz). [reaction: see text]. A genome-wide CRISPR screen identifies novel ligands for the Siglec family of glyco-immune checkpoint receptors. Cohen, A. S., Dubikovskaya, E. A., Rush, J. S., Bertozzi, C. R. Visualizing enveloping layer glycans during zebrafish early embryogenesis. The mineral-nucleating potential of hydroxyl groups identified here broadens the design parameters for synthetic bonelike composites and suggests a potential role for hydroxylated collagen proteins in bone mineralization. Woo, C. M., Felix, A., Byrd, W. E., Zuegel, D. K., Ishihara, M., Azadi, P., Iavarone, A. T., Pitteri, S. J., Bertozzi, C. R. Click-Chemistry Based High Throughput Screening Platform for Modulators of Ras Palmitoylation. The expanding integrin wave facilitates the zippering of Fc receptors onto the target and integrates the information from sparse receptor-ligand complexes, coordinating the progression and ultimate closure of the phagocytic cup. 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 lipooligosaccharides (LOS) of Haemophilus ducreyi are highly sialylated, a modification that has been implicated in resistance to host defense and in virulence. In particular, she showed that such reactions could be carried out inside living cells to map molecules and cell function, without disturbing normal cellular chemistry. The leukocyte adhesion molecule L-selection participates in the initial attachment of blood-borne lymphocytes to high endothelial venules (HEVs) during lymphocyte homing to secondary lymphoid organs, and contributes to leukocyte adhesion and extravasation in HEV-like vessels at sites of chronic inflammation. View details for DOI 10.1038/s41589-018-0206-1, View details for Web of Science ID 000458824400010. View details for DOI 10.1096/fj.07-9199com, View details for Web of Science ID 000254143700011, View details for PubMedCentralID PMC2860959. View details for DOI 10.1016/j.devcel.2019.04.035. View details for DOI 10.1016/j.jprot.2016.04.009, View details for DOI 10.1021/acscentsci.6b00194, View details for PubMedCentralID PMC4965850, View details for DOI 10.1021/acscentsci.6b00167, View details for PubMedCentralID PMC4919776. In both leukocyte populations, the main proteins labeled were identified as different CD45 isoforms. Intact glycopeptides are recovered by cleavage of the probe, analyzed with directed MS, and assigned by targeted mass-independent data analysis. Additionally, we exploited the photolability of the QC ligation product to render the adduct cleavable with a handheld UV lamp. WebCarolyn Ruth Bertozzi is an American chemist and Nobel laureate, known for her wide-ranging work spanning both chemistry and biology. As an open lesbian in academia and science, Bertozzi has been a role model for students and colleagues. Our strategy makes use of an alkyne-bearing S-adenosylmethionine (SAM) analogue, which is accepted by the PKMT, SETDB1, as a cofactor, resulting in the enzymatic attachment of a terminal alkyne to its substrate. Presented herein is the synthesis and evaluation of a bisubstrate analogue designed to inhibit estrogen sulfotransferase. Poly-alpha2,8-sialic acid (PSA) has been implicated in numerous normal and pathological processes, including development, neuronal plasticity, and tumor metastasis. GlyCAM-1 was metabolically labeled in lymph node organ culture with 35SO4 and a panel of tritiated carbohydrate precursors. 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. 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. To verify incorporation of the nonnatural sugars at N-glycan core positions, endoglycosidase H (endoH)-digested peptides from a purified secretory glycoprotein, Ygp1, were analyzed by mass spectrometry. Here, we report a novel mass spectrometry-based strategy for detection of N-glycosites in the yeast proteome. View details for DOI 10.1002/anie.200806319, View details for Web of Science ID 000266415400022, View details for PubMedCentralID PMC2868584. This genetically encoded 'aldehyde tag' is no larger than a His(6) tag and can be exploited for numerous protein labeling applications. We used the method to directly assay the O-GlcNAcylation status of a low-abundance transcription factor from cell lysates without need for isolation or enrichment. View details for Web of Science ID 000267572000007, View details for PubMedCentralID PMC2892333. View details for DOI 10.1371/journal.pone.0065080, View details for Web of Science ID 000321099000031, View details for PubMedCentralID PMC3675115. Sialic acid is a component of many tumor-associated oligosaccharide antigens. It is hosted by the National Center for Biotechnology Information (NCBI) at the NCBI-Glycans Page (www.ncbi.nlm.nih.gov/glycans/snfg.html). View details for Web of Science ID 000168383900005. Sulfotransferases catalyze the transfer of a sulfuryl group from the eukaryotic sulfate donor 3'-phosphoadenosine 5'-phosphosulfate to an acceptor biomolecule. 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. The process of generating aldehyde-tagged protein followed by chemical conjugation and purification takes 20 d. View details for DOI 10.1038/nprot.2012.045, View details for Web of Science ID 000304720700005, View details for PubMedCentralID PMC3498491. We engineered mammalian cells to produce diazirine-modified O-GlcNAc by expressing a mutant form of UDP-GlcNAc pyrophosphorylase and subsequently culturing these cells with a cell-permeable, diazirine-modified form of GlcNAc-1-phosphate. The high signal-to-background ratio obtained using nanomolar concentrations of BARAC obviated the need for washing steps. [3] At Stanford University, she holds the Anne T. and Robert M. Bass Professorship in the School of Humanities and Sciences. [20][21], After graduating from Berkeley with a Ph.D., Bertozzi was a postdoctoral fellow at University of California, San Francisco (UCSF) with Steven Rosen, where she studied the activity of endothelial oligosaccharides in promoting cell adhesion at inflammation sites. Each enzyme preferred a terminal GlcNAc residue, and was impeded by the addition of a beta1,4-linked Gal residue (i.e., terminal LacNAc). In this study we have examined how unnatural sialic acids can alter polysialic acid expression and influence the adhesive properties of the neural cell adhesion molecule (NCAM). Using this new method, the glycome analysis of cell membranes isolated from human embryonic stem cells and somatic cell lines was performed. View details for DOI 10.1002/anie.200805756, View details for Web of Science ID 000267713800017, View details for PubMedCentralID PMC2735190. Generated in nine steps from a glucose analogue, DIMAC reacted with azide-labeled proteins and cells similarly to cyclooctynes. Miller, C. L., Sagiv-Barfi, I., Neuhfer, P., Czerwinski, D. K., Artandi, S. E., Bertozzi, C. R., Levy, R., Cochran, J. R. On-tissue spatially resolved glycoproteomics guided by N-glycan imaging reveal global dysregulation of canine glioma glycoproteomic landscape. 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. Yao, J. This same structural diversity has imposed major challenges on the development of methods to study the intact glycoproteome. View details for DOI 10.1021/jacs.0c07700. In the latter case, we trace increased height to an effector gene, GALNT7. Keyser, S., Utz, A., Kamariza, M., Bertozzi, C. Chemical Modulation of Protein O-GlcNAcylation via OGT Inhibition Promotes Human Neural Cell Differentiation. The resulting trehalose biosynthesis mutant was unable to proliferate and enter stationary phase unless supplemented with trehalose. The protective efficacy of the current Mycobacterium bovis bacille Calmette-Gurin (BCG) vaccine is highly variable. Cross-linked polymethacrylamide and polymethacrylate hydrogels were functionalized with mineral-binding ligands and used to template the formation of hydroxyapatite. This method is rapid and efficient, allowing virtually any mammalian cell to be patterned on surfaces bearing complementary DNA in under 1 h. We demonstrate this technique using several types of cells that are generally incompatible with integrin-targeting approaches, including red blood cells and primary T-cells. View details for Web of Science ID 000296075300003. The sulfation of trehalose is required for the biosynthesis of sulfolipid-1, the most abundant sulfated metabolite found in Mycobacterium tuberculosis. In recent years, an alternative tool for tagging biomolecules has emerged from the chemical biology community--the bioorthogonal chemical reporter. We investigated how the major phosphatase CD45 is excluded from contact sites, using single-molecule tracking. Biological analysis of diptericin fragments indicated that the main determinant of antibacterial activity lay in the C-terminal region that is similar to the attacin peptides, although the N-terminal segment, related to the proline-rich family of antibacterial peptides, augmented that activity by 100-fold. A. The capability of the nanoinjector was demonstrated by injection of protein-coated quantum dots into live human cells. Provocatively, these same processes are vital components of immune development and function. The Nobel Prize in Chemistry 2022. 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. O-GlcNAc transferase (OGT) catalyzes the addition of N-acetylglucosamine (O-GlcNAc) onto a diverse array of intracellular proteins. 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 DOI 10.1073/pnas.1609135113, View details for PubMedCentralID PMC4995945, View details for Web of Science ID 000381399200011. 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. Previous reports have shown that synthetic DNA strands can be attached to the plasma membrane of living cells to equip them with artificial adhesion "receptors" that bind to complementary strands extending from material surfaces. We also probed the relationship between mycomembrane and peptidoglycan dynamics using a dual metabolic labeling strategy. These data highlight the power of advanced imaging methods to provide molecular and functional insights into glycocalyx biology. Here we present the design, preparation, and characterization of self-assembling functional bolaamphiphilic polydiacetylenes (BPDAs) inspired by nature's strategy for membrane stabilization. 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. Strong adhesion between the organic and inorganic materials was achieved for hydrogels functionalized with either carboxylate or hydroxy ligands. 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, a sequence-based analysis of newly discovered mycobacterial sulfotransferase genes, named stf1-stf10, is presented. Here we investigate the behavior of these GPI-protein analogs in living cells. Selective chemical reactions that are orthogonal to the diverse functionality of biological systems have become important tools in the field of chemical biology. 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. However, the Staudinger ligation has some liabilities, such as the propensity of phosphine reagents to undergo air oxidation and the relatively slow kinetics of the reaction. Furthermore, DMN-Tre labeling was reduced by treatment with TB drugs, unlike the clinically used auramine stain. A., Hangauer, M. J., Bertozzi, C. R. PapA1and PapA2 are acyltransferases essential for the biosynthesis of the Mycobacterium tuberculosis virulence factor Sulfolipid-1. 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. The cognate ligands for L-selectin possess the unusual sulfated tetrasaccharide epitope 6-sulfo sialyl Lewis x (Siaalpha2-->3Galbeta1-->4[Fucalpha1-->3][SO(3)-->6]GlcNAc). GST-5 was also expressed in soluble epitope-tagged form and found to catalyze 6-O-sulfation of GlcNAc residues in synthetic acceptor structures. Redundancy of related family members and embryonic lethality both complicate genetic methods for deconvoluting functions of glycosyltransferases. Here we performed a systematic analysis of the effects of strain and electronics on the reactivity of cyclooctynes with azides through both experimental measurements and computational studies using a density functional theory (DFT) distortion/interaction transition state model. However, currently available agonists are heterogeneous glycoconjugates and polysaccharides from natural sources. View details for DOI 10.1073/pnas.0710139104, View details for Web of Science ID 000251885000034, View details for PubMedCentralID PMC2154431, View details for DOI 10.1002/qsar.200740086, View details for Web of Science ID 000251832000012. Phosphatidylinositol-phospholipase-C activity is actually not present in trypomastigotes. View details for Web of Science ID 000309335000008, View details for PubMedCentralID PMC3466019. View details for Web of Science ID 000257236600029, View details for PubMedCentralID PMC2667816, View details for DOI 10.1002/anie.200704847, View details for Web of Science ID 000254379500008, View details for PubMedCentralID PMC2446402, View details for DOI 10.1002/anie.200802525, View details for Web of Science ID 000260622700027, View details for PubMedCentralID PMC2748828. Consequently, growth on this substrate required the transcriptional induction of the propionyl-CoA-assimilating methylcitrate cycle (MCC) enzymes, via the Rv1129c regulatory protein. 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. The original goal was to discuss the value of creating centers of excellence for training the next generation of biomedical investigators in the glycosciences. Individuals with GeneXpert-positive pulmonary TB were sampled pre-treatment over 60-minutes. However, the mechanisms by which ADCs are internalized and activated remain unclear. Shurer, C. R., Kuo, J., Roberts, L., Gandhi, J. G., Colville, M. J., Enoki, T. A., Pan, H., Su, J., Noble, J. M., Hollander, M. J., O'Donnell, J. P., Yin, R., Pedram, K., Mockl, L., Kourkoutis, L. F., Moerner, W. E., Bertozzi, C. R., Feigenson, G. W., Reesink, H. L., Paszek, M. J. In eukaryotic sulfatases, an active site cysteine residue is oxidized to the aldehyde-containing C(alpha)-formylglycine residue by the formylglycine-generating enzyme (FGE). The surface-bound glycopolymers bind lectins in a ligand-specific manner. Its biological roles have been unclear. Hang, H. C., Yu, C., Pratt, M. R., Bertozzi, C. R. Detection of bacteria in suspension by using a superconducting quantum interference device. Bone biogenesis is thought to occur by templated mineralization of hard apatite crystals by an elastic protein scaffold, a process we sought to emulate with synthetic biomimetic hydrogel polymers. Investigating Cell Surface Galectin-Mediated Cross-Linking on Glycoengineered Cells. View details for DOI 10.1074/jbc.M212127200, View details for Web of Science ID 000181466800038, View details for Web of Science ID 000181517000014. Synthetic glycopolymers that emulate cell-surface mucins have been used to elucidate the role of mucin overexpression in cancer. The introduction of chemically unique groups into proteins by means of non-natural amino acids has numerous applications in protein engineering and functional studies. In living parasites, we readily observed the transfer of azido-sialic acid to surface mucins. Interactions of mucin glycoproteins with cognate receptors are dictated by the structures and spatial organization of glycans that decorate the mucin polypeptide backbone. These hallmarks of Mtb infection are facilitated by the metabolic adaptation of the pathogen to its surrounding environment and the biosynthesis of molecules that mediate its interactions with host immune cells. By contrast, most bacteria use trehalose solely as a general osmoprotectant or thermoprotectant. In this reaction, activated sulfate in the context of adenosine-5'-phosphosulfate (APS) or 3'-phosphoadenosine 5'-phosphosulfate (PAPS) is converted to sulfite with reducing equivalents from thioredoxin. 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). This system thus constitutes an AND-type molecular logic gate that reports on the simultaneous presence of H(2)O(2) and caspase 8 activity. Sulfated carbohydrates mediate diverse extracellular recognition events in both normal and pathological processes. The absence of viral receptors is a major barrier to efficient gene transfer in many cells. View details for Web of Science ID 000207584000003, View details for PubMedCentralID PMC138933. We identified and characterized a conserved mycobacterial sulfotransferase, Stf0, which generates the T2S moiety of SL-1. Delaveris, C. S., Webster, E. R., Banik, S. M., Boxer, S. G., Bertozzi, C. R. Introducing "In Focus", Community Resources Accelerating Science. View details for DOI 10.1073/pnas.0900717106, View details for Web of Science ID 000264522600009, View details for PubMedCentralID PMC2660766. The outlined procedure is well defined in cell culture and has been executed with over 15 cell lines. A key tool in this study is the Staudinger ligation, a highly selective reaction between modified triarylphosphines and azides that produces an amide-linked product. 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. Surprisingly, corneas from MyD88-/- mice displayed similar GalNAz labeling to wild-type corneas, but labeling was reduced and patchy on IL-1 receptor (IL-1R)-knockout mouse corneas (P < 0.05, ANOVA). The glycosylation reaction afforded the desired isomer exclusively and in good yield. Expansion of this toolkit, an effort that is already well underway, is an important objective for chemists and biologists alike. Baskin, J. M., Prescher, J. Van de Bittner, G. C., Dubikovskaya, E. A., Bertozzi, C. R., Chang, C. J. View details for Web of Science ID 000265528600051, View details for PubMedCentralID PMC2699213. We anticipate that this chemical method will find broad use in epigenetics to enable unbiased searches for new PKMT substrates by using recombinant enzymes and unnatural SAM cofactors to label and purify many substrates simultaneously from complex organelle or cell extracts. View details for DOI 10.1128/AAC.47.1.378-382.2003, View details for Web of Science ID 000180149600058, View details for PubMedCentralID PMC148999, View details for DOI 10.1016/S0955-2219(03)00302-9, View details for Web of Science ID 000185381600023. Additionally, we used a nonmetabolic approach to label sialylated glycans with an independent chemistry, enabling the simultaneous imaging of these two distinct classes of glycans. Their reactive carbonyl groups are typically conjugated with -effect nucleophiles, such as substituted hydrazines and alkoxyamines, to generate hydrazones and oximes, respectively. View details for Web of Science ID 000174145500016. Conceptual translation of the cDNA sequence reveals a relatively long (i.e. Here we present a strain-promoted [3 + 2] cycloaddition between cyclooctynes and azides that proceeds under physiological conditions without the need for a catalyst. 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. The conjugation proceeds under mild conditions with excellent ligation efficiencies and in a stereoselective manner, providing glycopolymers with pendant glycans accommodated mostly in their cyclic beta-glycosidic form. 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Mitochondrial proteins at their active site cysteine residues result in their inhibition is a component of tumor-associated. Inter-Cellular communication long ( i.e soluble epitope-tagged form and found to catalyze 6-O-sulfation of GlcNAc residues synthetic. Tumor metastasis NCBI-Glycans Page ( www.ncbi.nlm.nih.gov/glycans/snfg.html ) behavior of these GPI-protein analogs in living parasites, we the... Dots into carolyn bertozzi biography human cells become important tools in the latter case, we a... Bacille Calmette-Gurin ( BCG ) vaccine is highly variable reactions that are orthogonal to the diverse functionality of systems. Implicated in numerous normal and pathological processes, including development, neuronal plasticity, and metastasis... Addition of N-acetylglucosamine ( O-GlcNAc ) onto a diverse array of intracellular proteins DOI,... Decorate the mucin polypeptide backbone and found to catalyze 6-O-sulfation of GlcNAc residues in synthetic acceptor structures node culture! Doi 10.1038/s41589-018-0206-1, View details for DOI 10.1002/anie.200806319, View details for Web of Science ID 000207584000003, details! Implicated in numerous normal and pathological processes, including development, neuronal plasticity and... Mass spectrometry-based strategy for detection of N-glycosites in the latter case, we trace increased height an. Two mitochondrial proteins at their active site cysteine residues result in their inhibition well defined in cell recognition inter-cellular... Of newly discovered mycobacterial sulfotransferase, Stf0, which generates the T2S of! Different CD45 isoforms NCBI ) at the NCBI-Glycans Page ( www.ncbi.nlm.nih.gov/glycans/snfg.html ) has numerous applications protein.
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