Here we show that the cytosolic enzyme N-glycanase 1 (NGLY1, the human PNGase) is essential for Nrf1 activation in response to proteasome inhibition. Tissue paper blotting removed GalNAz-labeled surface cells, causing DAPI labeling (permeabilization) of underlying cells. VDAC2(-/-) cells resist the mitochondrial dysfunction and apoptosis caused by global O-GlcNAc perturbation, demonstrating afunctional connection between O-GlcNAc signaling and mitochondrial physiology through VDAC2. This diffusion barrier is resolved through perforations in the peripheral peptidoglycan, thus leading to the confluency of the mycomembrane before daughter cell separation (V snapping). Here, we demonstrate that the presentation of additional anionic functional groups in the form of sulfate esters, on a polymerized liposome surface containing a multimeric array of sLe(x)-like oligosaccharides, generates a highly potent, bifunctional macromolecular assembly. To address this shortcoming, we have developed a robust, high-throughput compatible, click chemistry-based approach to identify small molecules that interfere with the palmitoylation of Ras, a high value therapeutic target that is mutated in up to a third of human cancers. We find the S-layer-on-mica system possesses a kinetic trap associated with conformational differences between a long-lived transient state and the final stable state. Furthermore, the method is found to be very specific, as after enrichment over 87% of all peptides contain (modified) azidohomoalanine. Pi, N., Hoang, M. B., Gao, H., Mougous, J. D., Bertozzi, C. R., Leary, J. This study reports the vaccine potential of an attenuated 5'-adenosine phosphosulfate reductase mutant (DeltacysH) of M. tuberculosis. Here we report that a truncated S-layer protein assembles into stable bilayers, which we characterized using cryogenic-electron microscopy, tomography, and X-ray spectroscopy. These receptors are promising targets for vaccine development and cancer immunotherapy. Disruption of cysH rendered Mtb auxotrophic for cysteine and methionine, and attenuated virulence in BALB/c and C57BL/6 immunocompetent mice. These data suggest that chemical inhibition of OGT and perturbation of protein O-GlcNAcylation accelerate the differentiation of hESCs along the neuronal lineage, thus providing further insight into the dynamic molecular mechanisms involved in neuronal development. Using a mass spectrometric approach to simultaneously monitor hundreds of lipids, we discovered that the size and abundance of two lipid virulence factors, phthiocerol dimycocerosate (PDIM) and sulfolipid-1 (SL-1), are controlled by the availability of a common precursor, methyl malonyl CoA (MMCoA). Marcaurelle, L. A., Rodriguez, E. C., Bertozzi, C. R. Direct incorporation of unprotected ketone groups into peptides during solid-phase synthesis: Application to the one-step modification of peptides with two different biophysical probes for FRET, Identification of an N-acetylglucosamine-6-O-sulfotransferase activity specific to lymphoid tissue: an enzyme with a possible role in lymphocyte homing. We report herein the chemical synthesis and preliminary mechanistic investigation of diptericin, an 82 residue glycopeptide that contains regions similar to two different types of antibacterial peptides. Here, we report a synergy between shape-generating processes in the cell interior and the external organization and composition of the cell-surface glycocalyx. We structurally assigned 32 N-glycopeptides and over 500 intact and fully elaborated O-glycopeptides from 250 proteins across three human cancer cell lines and also discovered unexpected peptide sequence polymorphisms (pSPs). Selectins are central in the inflammatory response; the discovery that they bind to carbohydrate ligands has galvanized carbohydrate chemists to search for inhibitors of the process. 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. View details for Web of Science ID 000281066400069, View details for PubMedCentralID PMC2923465. Our work provides insight into acute drug effects on cell envelope biogenesis in live mycobacteria. Dube, D. H., Prescher, J. In this work, we apply an aluminum "lift off" lithography method to allow the efficient generation of complex patterns comprising different DNA sequences. Nijmegen (2013), Honorary Doctorate Degree, Brown University (2012), Tetrahedron Young Investigator Award, Executive Board of Editors and the Publisher of Tetrahedron Publications (2011), Harrison Howe Award, Rochester Section, American Chemical Society (2009), W. H. Nichols Award, New York Section, American Chemical Society (2009), Li Ka Shing Women in Science Award, Li Ka Shing Foundation Women in Science Program (2008), Roy L. Whistler International Award in Carbohydrate Chemistry, International Carbohydrate Organization (2008), Willard Gibbs Medal, Chicago Section, American Chemical Society (2008), T.Z. This platform offers a new approach to exploring the "galectin lattice" hypothesis and to defining galectin ligand specificity in a physiologically relevant context. Current approaches offer a precision approaching that of genetic control. View details for DOI 10.1073/pnas.1321205110, View details for Web of Science ID 000328858800008, View details for DOI 10.1002/anie.201307512, View details for Web of Science ID 000328531100027, View details for PubMedCentralID PMC3920747. The enzymes that determine protein O-GlcNAcylation, O-GlcNAc transferase (OGT) and O-GlcNAcase (OGA), act on key transcriptional and epigenetic regulators, and both are abundantly expressed in the brain. The most potent examined, 1-68A, is a pH-dependent, two-step, covalent inhibitor of Escherichia coli LpxC that competes with UDP to bind the enzyme in the first step of inhibition. [reaction: see text]. 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. One mechanism of proteasome inhibitor resistance may involve the transcription factor Nuclear Factor, Erythroid 2 Like 1 (NFE2L1, also referred to as Nrf1), which responds to proteasome insufficiency or pharmacological inhibition by upregulating proteasome subunit gene expression. Synthetic Riboswitches That Induce Gene Expression in Diverse Bacterial Species. She coined the View details for Web of Science ID 000225233600024. They originate from biosynthetic pathways comprising an assembly line of glycosyltransferases within the Golgi compartment. WebCarolyn R. Bertozzi, in full Carolyn Ruth Bertozzi, (born October 10, 1966, Boston, Massachusetts), American chemist known for her application of chemical synthesis to the study of biological systems. Malaker, S. A., Quanico, J., Romero, A. R., Pascal, Q., Kobeissy, F., Abou-louard, S., Tierny, D., Bertozzi, C. R., Fornier, I., Salzet, M. O-Pair Search with MetaMorpheus for O-glycopeptide Characterization. Although hundreds of proteins are known to be modified by O-GlcNAc, a strict amino acid consensus sequence for OGT has not been identified. About that time, she also began mapping a specific glycana type of carbohydrate typically found on the surface of cellsthat specializes in attracting immune cells toward the lymph nodes. View details for DOI 10.1073/pnas.0700567104, View details for Web of Science ID 000246599900007, View details for PubMedCentralID PMC1895932. These bacteria are surrounded by a multilayered cell envelope composed of a cytoplasmic membrane, a peptidoglycan (PG) cell wall, a second polysaccharide layer called the arabinogalactan (AG), and finally an outer membrane-like layer made of mycolic acids. This technique causes no discernible membrane or cell damage, and can deliver a discrete number of molecules to the cell's interior without the requirement of a carrier solvent. IsoStamp has the potential to enhance any proteomics platform that employs chemical labeling for targeted protein identification, including isotope coded affinity tagging, isobaric tagging for relative and absolute quantitation, and chemical tagging strategies for posttranslational modification. Palaniappan, K. K., Hangauer, M. J., Smith, T. J., Smart, B. P., Pitcher, A. Genes involved in cell signaling, extracellular matrix remodeling, inflammation, angiogenesis and hypoxia were all activated in cells on the collagen-GAG mesh. Most current diagnostic tests for tuberculosis do not reveal the species or strain of pathogen causing pulmonary infection, which can lead to inappropriate treatment regimens and the spread of disease. This novel assay may improve pediatric testing compliance and facilitate easier community-wide screening for islet autoantibodies. The reaction of azides with strained alkynes, such as cyclooctynes, readily forms a triazole product without the need for a toxic catalyst. View details for Web of Science ID 000085780300001, View details for Web of Science ID 000086418600036, View details for Web of Science ID 000165500500020, View details for Web of Science ID 000084512700012. A., Bertozzi, C. R. Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation. Driessen, M. D., Going, C. C., Woo, C. M., Pitteri, S. J., Bertozzi, C. R. New therapeutic avenues for NGLY1 deficiency, A TENSION-MEDIATED GLYCOCALYX FEEDBACK LOOP PROMOTES A MESENCHYMAL, STEM-LIKE PHENOTYPE IN GLIOBLASTOMA. 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). Azido sugars are fed to cells or organisms and integrated by the glycan biosynthetic machinery into various glycoconjugates. The cell-surface repertoire can be expanded to include abiotic functionality through the biosynthetic introduction of unnatural sugars into cellular glycans, a process termed metabolic oligosaccharide engineering. Woo, C. M., Lund, P. J., Huang, A. C., Davis, M. M., Bertozzi, C. R., Pitteri, S. n. Imaging Mycobacterial Trehalose Glycolipids. Bertozzi has applied the techniques of bioorthogonal chemistry to study glycocalyx, the sugars that surround the cell membrane. Proteomics analyses were also performed and confirmed enrichment of plasma membrane proteins with some contamination from endoplasmic reticulum and other membranes. In 1961, Wittig and Krebs noted that the strained, cyclic alkyne cyclooctyne reacts violently when combined neat with phenyl azide, forming a triazole product by 1,3-dipolar cycloaddition. In contrast, polySia expression and function in the nervous system has been well characterized. We demonstrate binding of all three selectins to GlyCAM-1 and demonstrate that the binding interactions satisfy a number of important criteria. In addition, the mode of inhibition for PAP was rapidly determined. The sulfite generated in this reaction is utilized in bacteria and plants for the eventual production of essential biomolecules such as cysteine and coenzyme A. We developed a new fluorophore-trehalose conjugate to visualize trehalose monomycolates of the mycomembrane using super-resolution microscopy. Breidenbach, M. A., Palaniappan, K. K., Pitcher, A. Proteasome inhibitors are used to treat blood cancers such as multiple myeloma (MM) and mantle cell lymphoma. Instead, MECA-79 bound preferentially to 6-sulfolactose. The synthetic sugar decorated the cell surface with a unique ketone group that served as a foundation on which we built an adenovirus receptor by covalently binding biotin hydrazide to the ketone. Our results suggest a correlation between decreased alkyne bond angle and increased cyclooctyne reactivity. a nanoscience research center at Lawrence Berkeley National Laboratory. Here we describe the identification of a prokaryotic FGE from Mycobacterium tuberculosis. Atoms out of Blobs: CryoEM Takes the Nobel Prize in Chemistry. We report that cell surface PSA expression can be reversibly inhibited by a small molecule, N-butanoylmannosamine (ManBut). All mucin-associated [(35)S]sulfate was incorporated as GlcNAc-6-sulfate or Galbeta1-->4GlcNAc-6-sulfate. Despite proven disease relevance, correlating the activity of individual GalNAc-Ts with biological function remains challenging due to a lack of tools to probe their substrate specificity in a complex biological environment. View details for Web of Science ID 000207584000003, View details for PubMedCentralID PMC138933. The utility of this approach is demonstrated through the observation of patterned cells as they communicate by diffusion-based paracrine signaling. The correlation of its abundance with the virulence of clinical isolates suggests a role for SL-I in pathogenesis, although its biological functions remain unknown. View details for DOI 10.1016/j.bmc.2005.04.085, View details for Web of Science ID 000231341900006. These findings elucidate a mechanism of age-related microglial impairment and a strategy to restore homeostasis in the ageing brain. Intact glycopeptides are recovered by cleavage of the probe, analyzed with directed MS, and assigned by targeted mass-independent data analysis. Thus, we hypothesize that either MmpL8 transports molecules in addition to SL-1 that mediate host-pathogen interactions or the accumulation of SL(1278) in mmpL8 mutant cells interferes with other pathways required for growth during the early stages of infection. View details for DOI 10.1073/pnas.0437851100, View details for Web of Science ID 000181675200023, View details for PubMedCentralID PMC152251. Recent work has implicated tyrosine sulfate as a determinant of protein-protein interactions involved in leukocyte adhesion, hemostasis and chemokine signaling. We also found that StcE digests cancer-associated mucins from cultured cells and from ascites fluid derived from patients with ovarian cancer. Synthetically lipidated recombinant green fluorescent protein (GFP) was shown to be stably anchored to the membrane, and its lateral fluidity was quantitatively characterized by direct fluorescence imaging in supported membranes. Chemical biotinylation followed by enrichment and mass spectrometry led to the identification of glycoproteins that were found at elevated levels or uniquely in cancerous prostate tissue. Under these conditions, Nrf1 is inactive in regulating proteasome subunit gene expression in response to proteasome inhibition. Strategies to ameliorate GBM tissue tension offer a therapeutic approach to reduce mortality due to GBM. Bertozzi, C. R., Fukuda, S., ROSEN, S. D. CRACKING THE CARBOHYDRATE CODE FOR SELECTIN RECOGNITION, IDENTIFICATION OF THE SULFATED MONOSACCHARIDES OF GLYCAM-1, AN ENDOTHELIAL-DERIVED LIGAND FOR L-SELECTIN. Gilmore, S. A., Schelle, M. W., Holsclaw, C. M., Leigh, C. D., Jain, M., Cox, J. S., Leary, J. View details for Web of Science ID 000311072900014, View details for PubMedCentralID PMC3500440. While these variables are easily excluded or avoided in reconstituted systems, they must be dealt with in cellular environments. A Pragmatic Guide to Enrichment Strategies for Mass Spectrometry-based Glycoproteomics. Recent insights into the domain architecture, localization and regulation of glycosyltransferases have provided a platform for engineering their position within the secretory pathway and access to substrates. View details for DOI 10.1016/j.cbpa.2003.08.006, View details for Web of Science ID 000186448100015. Poor diagnostic tools to detect active disease plague TB control programs and affect patient care. Mycobacterium tuberculosis, the causative agent of tuberculosis, produces unique sulfated metabolites associated with virulence. Flynn, R. A., Belk, J. These observations suggest crosstalk between autophagy and phagocytosis that may be relevant to the innate immune response of macrophages. Further, enzymatically simplified N-glycans are preserved on peptides. We found that N-azidoacetylgalactosamine (GalNAz) is converted by endogenous mammalian biosynthetic enzymes to UDP-GalNAz and then epimerized to UDP-N-azidoacetylglucosamine (GlcNAz). Biosynthetic pathways comprising an assembly line of glycosyltransferases within the Golgi compartment enrichment. And C57BL/6 immunocompetent mice Gene expression in Diverse Bacterial Species system possesses kinetic... 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