View details for Web of Science ID 000177962200018. Changes in O-linked protein glycosylation are known to correlate with disease states but are difficult to monitor in a physiological setting because of a lack of experimental tools. Homogeneously glycosylated proteins are important targets for fundamental research and for biopharmaceutical development. Cohen, A. S., Dubikovskaya, E. A., Rush, J. S., Bertozzi, C. R. Visualizing enveloping layer glycans during zebrafish early embryogenesis. Fusion of these domains to the proteins FRB and FKBP enabled their induced assembly by the natural product rapamycin. Grand Challenges in Chemistry for 2016 and Beyond. N610 was also the primary site of sialylation of the receptor. Here we show that a stf0-deletion mutant exhibits augmented survival in human but not murine macrophages, suggesting that SL-1 negatively regulates the intracellular growth of Mtb in a species-specific manner. Oligosaccharides on proteins and lipids play central roles in human health and disease. However, the estimated barrier is much smaller than expected for folding of isolated S-layer proteins, suggesting an energetic rationale for this multistage pathway. However, little is known about how alterations in O-GlcNAc cycling affect human embryonic stem cell (hESC) neural differentiation. The method was applied to assay for the heparin substrate specificity of a newly discovered human extracellular endosulfatase, HSulf-2, which has been implicated in tumorigenesis. 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. Membrane-proximal N-linked glycosylation was critical for maintaining the ligand dependence of the receptor. View details for DOI 10.1016/j.molcel.2020.03.030. Highly reactive cyclooctynes have been sought as substrates for Cu-free cycloaddition reactions with azides in biological systems. View details for Web of Science ID 000280086800002, View details for PubMedCentralID PMC2907715, View details for DOI 10.1016/j.cplett.2010.04.067, View details for Web of Science ID 000279368000001. GPI-anchored proteins are structurally and functionally diverse and play vital roles in numerous biological processes. The APS reductase structure reveals adaptive use of a phosphate-binding loop for recognition of the APS O3' hydroxyl group, or the PAPS 3'-phosphate group. View details for DOI 10.1016/j.jmb.2006.08.080, View details for Web of Science ID 000242160600003, View details for PubMedCentralID PMC1769331. A 56-member glycopeptide library designed to reflect a diversity of glycan clustering was assayed for substrate activity with ppGalNAcT isoforms using an azido-ELISA. The glycan-binding proteins, or lectins, that interact with mucins are often oligomeric receptors with multiple ligand binding domains. [27][41], Bertozzi became a co-founder of Palleon Pharma of Waltham, Massachusetts, in 2015. In addition, GalNAz efficiently labeled mucin-type O-linked glycoproteins expressed at endogenous levels. Her research group profiles changes in cell surface glycosylation associated with cancer, inflammation and bacterial infection, and uses this information to develop new diagnostic and therapeutic approaches, most recently in the area of immuno-oncology. The data presented here was obtained with the application of a bioorthogonal chemical reporter strategy analyzing differential glycoprotein expression following the knock-down (KD) of the GALNT3 gene in the epithelial ovarian cancer (EOC) cell line A2780s. Clinical studies revealed that large glycoproteins are abundantly expressed on circulating tumour cells from patients with advanced disease. Bertozzi developed a new type of reaction, now called a bioorthogonal reaction, that can occur in living environmentsrather than just in labswith no interference with other biochemical processes. A., Bertozzi, C. R. Global gene expression of cells attached to a tissue engineering scaffold, Directing flux in glycan biosynthetic pathways with a small molecule switch. A novel and efficient enzyme kinetics assay using electrospray ionization mass spectrometry was developed and applied to the bacterial carbohydrate sulfotransferase (NodST). Here we develop a combined genetic and chemical approach that enables introduction of the diazirine photocrosslinker onto the O-GlcNAc modification in cells. We designed synthetically tractable glycosylated polymers that possess rodlike extended conformations similar to natural mucins. Application of the IsoTaG platform to 15 cell lines metabolically labeled with Ac4GalNAz or Ac4ManNAz revealed 1375 N- and 2159 O-glycopeptides, variously modified with 74 discrete glycan structures. Wei, W., Riley, N. M., Lyu, X., Bertozzi, C. R., Long, J. 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. Lastly, DMN-Tre labeled Mtb in TB-positive human sputum samples comparably to auramine staining, suggesting that this operationally simple method may be deployable for TB diagnosis. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. View details for DOI 10.1074/jbc.M111619200, View details for Web of Science ID 000174400600071. To obtain structural information about these biomolecules, and the modifications they may undergo during different stages of cell growth and development, a mass spectrometry-based method was developed and used to obtain unambiguous structural information on the glycosaminoglycans (GAGs) that comprise heparin/HS. Here we introduce click-EM, a labeling technique for correlative light microscopy and EM imaging of nonprotein biomolecules. 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. Bertozzi remains a part of the advisory board for the biologics sector of the company. [27][28][29] This new field and technique allows researchers to chemically modify molecules in living organisms and not interrupt the processes of the cell. We demonstrated the noninvasive imaging of glycans in live developing zebrafish, using a chemical reporter strategy. Moreover, concomitant use of PCL-2 and IETDC in vivo establishes a concurrent increase in both H(2)O(2) and caspase 8 activity during acute inflammation in living mice. Here we describe a strategy for the use of a caged metabolic precursor that is activated for cellular metabolism by enzymatic cleavage. View details for Web of Science ID 000173233300006, View details for PubMedCentralID PMC117506. Mougous, J. D., Lee, D. H., Hubbard, S. C., Schelle, M. W., Vocadlo, D. J., Berger, J. M., Bertozzi, C. R. An alpha-formylglycine building block for Fmoc-based solid-phase peptide synthesis, Programmable cell adhesion encoded by DNA hybridization. The dependence of the desiccation protection on the synthetic trehalose glycolipid fraction is nearly identical to that of TDM. 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. 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. Using comprehensive identification of RNA-binding proteins by mass spectrometry (ChIRP-MS), we took an RNA-centric viewpoint of flaviviral infection and identified several hundred proteins associated with both DENV and ZIKV genomic RNA in human cells. View details for DOI 10.1021/acsomega.0c00071, View details for PubMedCentralID PMC7114878. In the 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. Here we report the in vitro activity of the four GlcNAc-6-sulfotransferases on a panel of synthetic oligosaccharide substrates that comprise structural motifs derived from sialyl Lewis x. Bacterial sulfate assimilation pathways provide for activation of inorganic sulfur for the biosynthesis of cysteine and methionine, through either adenosine 5'-phosphosulfate (APS) or 3'-phosphoadenosine 5'-phosphosulfate (PAPS) as intermediates. Shui, W., Gilmore, S. A., Sheu, L., Liu, J., Keasling, J. D., Bertozzi, C. R. Synthesis, Characterization, and Theory of [9]-, [12]-, and [18]Cycloparaphenylene: Carbon Nanohoop Structures. Chen, X., Kis, A., Zettl, A., Bertozzi, C. R. Hierarchical assembly of model cell surfaces: Synthesis of mucin mimetic polymers and their display on supported bilayers. View details for DOI 10.1021/acschembio.7b00232, View details for PubMedCentralID PMC5850955. The loss of SL-1 (and SL(1278)) did not appear to affect bacterial replication or trafficking, suggesting that the functions of SL-1 are specific to human infection. GST-5 is the newest member of an emerging family of carbohydrate 6-O-sulfotransferases that includes chondroitin 6-sulfotransferase (GST-0), keratan-sulfate galactose 6-O-sulfotransferase (GST-1), the ubiquitously expressed GlcNAc 6-O-sulfotransferase (GST-2), high endothelial cell GlcNAc 6-O-sulfotransferase (GST-3), and intestinal GlcNAc 6-O-sulfotransferase (GST-4). Additionally, we observe enhanced glycocalyx height in response to epithelial-to-mesenchymal transition and to oncogenic KRAS activation. Ahn, G., Banik, S. M., Miller, C. L., Riley, N. M., Cochran, J. R., Bertozzi, C. R. Degradation from the outside in: targeting extracellular and membrane proteins for degradation through the endolysosomal pathway. [45], In 2019, she co-founded both OliLux Biosciences and Lycia Therapeutics. Song, J., Xu, J., Filion, T., Saiz, E., Tomsia, A. P., Lian, J. View details for Web of Science ID 000250260500015. Pluvinage, J. V., Haney, M. S., Smith, B. The molecular analysis of glycoconjugate function has benefited tremendously from new methods for their chemical synthesis, which provides homogeneous material not attainable from biosynthetic systems. Sulfolipid-I (SL-I) is an abundant metabolite found in the cell wall of Mycobacterium tuberculosis that is comprised of a trehalose 2-sulfate core modified with four fatty acyl substituents. Li phin vn-chng si to pan-lan-chhan , ng cho-tet yung phin-si fet-ch khok-chhng kh ke nui-yng. The genome of Mycobacterium tuberculosis (Mtb) encodes nine putative sulfatases, none of which have a known function or substrate. These data provide strong evidence that Stf0 carries out the first committed step in the biosynthesis of SL-1 and establish a system for probing the role of SL-1 in M. tuberculosis infection. One challenge for the development of such probes is the a priori identification of structures that will undergo a dramatic fluorescence enhancement by virtue of the chemical transformation. 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. A. Mineralization of synthetic polymer scaffolds: A bottom-up approach for the development of artificial bone, Mechanistic investigation of the Staudinger ligation. We then rendered the yeast auxotrophic for production of the donor nucleotide-sugar uridine-diphosphate-GlcNAc (UDP-GlcNAc) by deletion of the essential gene GNA1. Gordon, C. G., Mackey, J. L., Jewett, J. C., Sletten, E. M., Houk, K. N., Bertozzi, C. R. Mapping Yeast N-Glycosites with Isotopically Recoded Glycans. During Bertozzi's third year of graduate school, Bednarski was diagnosed with colon cancer, which resulted in him taking a leave of absence and changing his career path by enrolling in medical school. However, disruption of the dimer by mutagenesis did not affect either localization or substrate preference. Herein, we designed and synthesized the first chemically defined ligands for dectin-1 and dectin-2. 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. Here, we describe how pH-dependent partitioning drives asymmetric antimicrobial drug distribution in M. tuberculosis-infected macrophages. The synthetic trehalose glycolipids protected supported monolayers of phospholipids against dehydration even as minority components of the overall membrane, down to as little as 20 mol % trehalose glycolipid as assessed by assays of membrane fluidity. This work suggests that BNNTs may be superior to CNTs for use as biological probes and in biomaterials. Site-directed mutagenesis of any cysteine residue within the conserved motif led to a loss of cluster with a concomitant loss in catalytic activity, while secondary structure was preserved. From 1996 to 2015, she was a professor of Chemistry View details for DOI 10.1016/j.cub.2020.09.082. Characterizing their peptide and glycopeptide substrate specificity is critical for understanding the biological role and significance of each isoform. A critical branch point in mucin-type oligosaccharides is the beta 1-->3 glycosidic linkage to the core alpha-N-acetylgalactosamine (GalNAc) residue. Assays based on solid-phase immobilization of antigens comprise the majority of clinical platforms for antibody detection, but can be undermined by antigen denaturation and epitope masking. Here we introduce a Pictet-Spengler ligation that is based on the classic Pictet-Spengler reaction of aldehydes and tryptamine nucleophiles. However, inside infected macrophages, bacteria encounter an environment which differs substantially from broth culture and are subject to important host-dependent pharmacokinetic phenomena which modulate drug activity. We exploited StcE's unique properties to improve sequence coverage, glycosite mapping, and glycoform analysis of recombinant human mucins by mass spectrometry. View details for DOI 10.1096/fj.201601198R, View details for Web of Science ID 000401553400015, View details for PubMedCentralID PMC5434651, View details for DOI 10.1021/acscentsci.7b00204, View details for PubMedCentralID PMC5445543. She is known for creating the term "bioorthogonal chemistry" for chemical reactions with living systems. Changes in their sulfation pattern and domain organization have been associated with different pathological situations such as viral infectivity, tumor growth, and metastasis. View details for DOI 10.1371/journal.pbio.0030250, View details for Web of Science ID 000231243800014, View details for PubMedCentralID PMC1175818. Their large size and extensive glycosylation makes the synthesis of these biopolymers impractical. Metabolic alterations observed during cholesterol catabolism centered on propionyl-CoA and pyruvate pools. 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. The azidofluorescein derivative also enabled cell imaging under no-wash conditions with good signal above background. The first synthesis and characterization of [9]-, [12]-, and [18]cycloparaphenylene was demonstrated utilizing a novel aromatization reaction. At 60 hours after fertilization, we observed an increase in de novo glycan biosynthesis in the jaw region, pectoral fins, and olfactory organs. The sulfotransferases share similar overall architecture with the exception of an extended stem region in GlcNAc6ST-1 that is absent in GlcNAc6ST-2. The prokaryotic homolog exhibits remarkable structural similarity to human FGE, including the position of catalytic cysteine residues. Multicellular organs comprise differentiated cell types with discrete yet interdependent functions. She is the 50th American Cancer Society -funded researcher and the first woman researcher funded by ACS to win the prestigious honor. Both mutant synthetases label human, hamster, and mouse cell line proteins and selectively activate their azido-bearing amino acids over 10-fold above the canonical. View details for DOI 10.1016/j.cell.2015.11.048, View details for PubMedCentralID PMC4715264. Here we report two engineered aminoacyl-tRNA synthetases for mammalian bioorthogonal labeling: a tyrosyl ( ScTyrY43G) and a phenylalanyl ( MmPheT413G) tRNA synthetase that incorporate azide-bearing noncanonical amino acids specifically into the nascent proteomes of host cells. Imaging analysis of glycan trafficking revealed dramatic reorganization of glycans on the second time scale, including rapid migration to the cleavage furrow of mitotic cells. Chemically tunable mucin chimeras assembled on living cells. 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. Mycobacterium tuberculosis and Mycobacterium smegmatis possess three pathways for the synthesis of trehalose. Furthermore, we demonstrate that the metabolic diversity of nature enables the use of naturally occurring functional groups that display inherent biocompatibility alongside abiotic components for organism-specific applications. The recently described O-glycoprotease OpeRATOR presents exciting opportunities for O-glycoproteomics. 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. 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). The antibodies recognized cells that were fed the unnatural biosynthetic precursor, and were capable of directing complement-mediated lysis.Structural alteration of sialic acids replaces a tolerized self-antigen with an antigenic determinant. Carroll, K. S., Gao, H., Chen, H. Y., Leary, J. Manning, D. D., Bertozzi, C. R., ROSEN, S. D., Kiessling, L. L. C-glycosyl aldehydes: Synthons for C-linked disaccharides. Our findings suggest that differential glycosylation at the level of tissue microanatomy regulates the nuclear function of Gal-1 in the context of mammary gland morphogenesis and in cancer progression. 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. View details for Web of Science ID 000088039800042. The reaction of azides with strained alkynes, such as cyclooctynes, readily forms a triazole product without the need for a toxic catalyst. The route developed for the model compound can be readily extended to the synthesis of native SL-I as well as additional analogues for use in the investigation of SL-I's functions. This heterogeneity precludes enrichment strategies that can be universally beneficial for all glycan classes. Vocadlo, D. J., Hang, H. C., Kim, E. J., Hanover, J. She completed her undergraduate degree in Chemistry from Harvard University in 1988 and her Ph.D. in Chemistry from UC Berkeley in 1993. These findings suggest a dual role for trehalose as both a thermoprotectant and a precursor of critical cell wall metabolites. DNA origami protection and molecular interfacing through engineered sequence-defined peptoids. 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. After completing postdoctoral work at UCSF in the field of cellular immunology, she joined the UC Berkeley faculty in 1996. There is urgent need for new therapeutic targets and a better understanding of EOC initiation and progression. The resulting surfaces are then demonstrated to be able to capture up to three distinct types of living cells in specific locations. Human embryonic stem cells were found to have high levels of high mannose glycans, which contrasts with IMR-90 fibroblasts and a human normal breast cell line, where complex glycans are by far the most abundant and high mannose glycans are minor components. In these experiments she applied click chemistry using an azide and an alkyne group to generate a ring-shaped molecule capable of binding to a modified sugar known as sialic acid on the glycan molecule. Sialic acid is a component of many tumor-associated oligosaccharide antigens. 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. A., Smart, B. P., Spiciarich, D. R., Iavarone, A. T., Bertozzi, C. R. The Regulation of Sulfur Metabolism in Mycobacterium tuberculosis, Metabolic Labeling of Fucosylated Glycans in Developing Zebrafish. Sialylation, sulfation, and fucosylation appear to be required for the avid interaction of this ligand with L-selectin, but the exact carbohydrate structures involved in recognition remain undefined. 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. Here, we systematically explore the advantages and disadvantages of conventional HCD, sceHCD, ETD, and EThcD for intact glycopeptide analysis and determine their suitability for both N- and O-glycoproteomic applications. The cysH mutant was also susceptible to peroxynitrite and hydrogen peroxide in vitro. Despite its ubiquity and essentiality in mammals, functional roles for the O-GlcNAc modification remain poorly defined. The development of bioorthogonal reactions has classically focused on bond-forming ligation reactions. We anticipate that these riboswitches will be useful tools for genetic studies in a wide range of bacteria. summa cum laude in chemistry from Harvard University, where she worked with Professor Joe Grabowski on the design and construction of a photoacoustic calorimeter. Her recent efforts include synthesis of chemical tools to study cell surface sugars called glycans and how they affect diseases View details for Web of Science ID 000177054900001, View details for Web of Science ID 000175790100030, Here we report a concise stereoselective synthesis of myo-inositol via ring-closing metathesis. Dibenzoselenacycloheptynes were prepared in three steps from commercially available reagents and trapped in situ with benzyl azide to form the corresponding triazoles. 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. A Fourier transform ion cyclotron resonance mass spectrometer provided accurate mass measurements, and a quadrupole time-of-flight instrument was used to obtain characteristic fragment ions and partial carbohydrate sequences. 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. We developed a multiplex analysis platform based on antibody detection by agglutination-PCR (ADAP) for the sample-sparing measurement of GAD, IA-2 and insulin autoantibodies/antibodies in 1 muL serum. FGE has emerged as an enabling biotechnology tool due to the robust utility of the aldehyde product as a bioconjugation handle in recombinant proteins. Here, we engineer living cells to tag glycans with editable chemical functionalities while providing information on biosynthesis, physiological context, and glycan fine structure. Cell surface reactions of this kind should prove useful in the introduction of new recognition epitopes, such as peptides, oligosaccharides, or small organic molecules, onto cell surfaces and in the subsequent modulation of cell-cell or cell-small molecule binding events. Accordingly, treatment of cells with N-azidoacetylglucosamine results in the metabolic incorporation of the azido sugar into nuclear and cytoplasmic proteins. Tyrosine sulfation is a post-translational modification of many secreted and membrane-bound proteins. 27 ] [ 41 ], Bertozzi, C. R., Long, J of... The receptor a dual role for trehalose as both a thermoprotectant and a better understanding of EOC initiation progression! This work suggests that BNNTs may be superior to CNTs for use as biological and... Smegmatis possess three pathways for the biologics sector of the essential gene GNA1, disruption the! Homogeneously glycosylated proteins carolyn bertozzi biography important targets for fundamental research and for biopharmaceutical development such cyclooctynes... In addition, GalNAz efficiently labeled mucin-type O-linked glycoproteins expressed at endogenous levels KRAS activation glycolipid! 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carolyn bertozzi biography