Agarwal, P., Beahm, B. J., Shieh, P., Bertozzi, C. R. Live-Cell Labeling of Specific Protein Glycoforms by Proximity-Enhanced Bioorthogonal Ligation. A., Cheng, E. H., Bertozzi, C. R., Boyce, M. Modulation of Ocular Surface Glycocalyx Barrier Function by a Galectin-3 N-terminal Deletion Mutant and Membrane-Anchored Synthetic Glycopolymers. It is hosted by the National Center for Biotechnology Information (NCBI) at the NCBI-Glycans Page (www.ncbi.nlm.nih.gov/glycans/snfg.html). Recent studies suggest that the mucin granule lumen consists of a matrix meshwork embedded in a fluid phase. The oligonucleotides were introduced using metabolic carbohydrate engineering, which allowed reactive tailoring of the cell surface glycans for chemoselective bioconjugation. Thus, this metabolic gene of an intracellular pathogen could have a secondary role in protection against the host immune response. By mutating catalytic residues of two such enzymes, we engineered mucin-selective binding agents with retained glycoform preferences. Here, we describe a method for visualizing and analyzing organelle- and stimulus-specific O-GlcNAcylated proteins and use it to identify the mitochondrial voltage-dependent anion channel 2 (VDAC2) as an O-GlcNAc substrate. EM has long been the main technique for imaging cell structures with nanometer resolution but has lagged behind light microscopy in the crucial ability to make specific molecules stand out. 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. A chemical transformation that permits the selective formation of covalent adducts among richly functionalized biopolymers within a cellular context is presented. [structure: see text] Divergent syntheses of sulfated sialyl Lewis X oligosaccharides corresponding to the core 1 and core 6 branches of the L-selectin ligand are reported. However, when activity of the vacuolar H+-ATPase was also inhibited, disulfide reduction decreased SHGFP-MUC5AC/CK t((1/2)) while diminishing its intraluminal concentration. This bifunctional microelectrode array is demonstrated for the pH monitoring and differentiation of primary T cells and Jurkat T lymphoma cells. However, detailed studies of these events are hampered by the heterogeneous nature of biosynthetic glycoproteins that typically exist in numerous glycoforms. Recurrent GBMs often exhibit mesenchymal, stem-like phenotypes that could explain their resistance to therapy. Here the identification of a series of uridine-based LpxC inhibitors is presented. Here we studied the function of novel germline variants in CSF3R at amino acid N610. Van de Bittner, G. C., Dubikovskaya, E. A., Bertozzi, C. R., Chang, C. J. Metabolic precision labeling enables selective probing of O-linked N-acetylgalactosamine glycosylation. We present a novel glycodendron prosthetic which can be site-selectively appended to recombinant proteins to create 'N-glycosylated' glycoprotein mimics. The approach was validated by labeling a recombinant glycoprotein that is known to possess O-linked glycans with GalNAz. We report the discovery that boron nitride nanotubes (BNNTs), isosteres of CNTs with unique physical properties, are inherently noncytotoxic. Here, we characterize Mtb's single putative type II sulfatase, Rv3406, as a non-heme iron (II) and -ketoglutarate-dependent dioxygenase that catalyzes the oxidation and subsequent cleavage of alkyl sulfate esters. Cell-surface glycans are attractive targets for molecule imaging due to their reflection of cellular processes associated with development and disease progression. Among the biomolecules that might be targeted for imaging analysis, glycans occupy a privileged position by virtue of their primary location on the cell surface. In contrast, polySia expression and function in the nervous system has been well characterized. The glycan symbol nomenclature proposed by Harvey et al. However, changes in the glycan structure significantly affected membrane mobility, with the loss of monosaccharide units correlating to decreased diffusion. View details for DOI 10.1074/mcp.M111.010660, View details for Web of Science ID 000302786500006, View details for PubMedCentralID PMC3322563. Collectively, these results indicate that the distortion/interaction model combined with bond angle analysis will enable predictions of cyclooctyne reactivity and the rational design of new reagents for copper-free click chemistry. Our results suggest that both Gal-6-SO(4) and GlcNAc-6-SO(4) may contribute to L-selectin recognition, either as components of sulfosialyl-Le(X) capping groups or in internal structures. These correlations have been challenging to uncover and establish because tools that specifically probe mucin domains are lacking. We developed a poly(acryloyl hydrazide) (PAH) scaffold to which we conjugated a variety of reducing glycans ranging in structure from simple mono- and disaccharides to considerably more complex human milk and blood oligosaccharides. We also probed the relationship between mycomembrane and peptidoglycan dynamics using a dual metabolic labeling strategy. View details for DOI 10.1073/pnas.0807820106, View details for Web of Science ID 000263844100008, View details for PubMedCentralID PMC2651276. Disruption of the cell architecture increased the number and the molecular weight distribution of azido-sialic acid tagged proteins. Molecules terminated with Texas Red lie flat at the membrane (height, 0 +/- 2 nm), implying that interactions between Texas Red and the bilayer dominate the polymers' free energy. These receptors have attracted great attention in recent years due to their participation in a number of acute and chronic inflammatory diseases. As an open lesbian in academia and science, Bertozzi has been a role model for students and colleagues. The sulfotransferases that generate specific carbohydrate 'sulfoforms' have recently been recognized as key modulators of these processes and therefore represent potential therapeutic targets. Tsai, C., Robinson, P. V., Spencer, C. A., Bertozzi, C. R. Amit, I., Baker, D., Barker, R., Berger, B., Bertozzi, C., Bhatia, S., Biffi, A., Demichelis, F., Doudna, J., Dowdy, S. F., Endy, D., Helmstaedter, M., Junca, H., June, C., Kamb, S., Khvorova, A., Kim, D., Kim, J., Krishnan, Y., Lakadamyali, M., Lappalainen, T., Lewin, S., Liao, J., Loman, N., Lundberg, E., Lynd, L., Martin, C., Mellman, I., Miyawaki, A., Mummery, C., Nelson, K., Paz, J., Peralta-Yahya, P., Picotti, P., Polyak, K., Prather, K., Qin, J., Quake, S., Regev, A., Rogers, J. Agard, N. J., Baskin, J. M., Prescher, J. Using CRISPR-Cas9 screens, we uncover many known and novel endolysosomal regulators as modulators of ADC toxicity. Bruehl, R. E., Bertozzi, C. R., ROSEN, S. D. Biosynthetic incorporation of unnatural sialic acids into polysialic acid on neural cells, Differential carbohydrate recognition of two GlcNAc-6-sulfotransferases with possible roles in L-selectin ligand biosynthesis. Alternatively, selective inhibition or activation of glycosyltransferases or glycosidases can define the biological roles of the corresponding glycans. We also found that StcE digests cancer-associated mucins from cultured cells and from ascites fluid derived from patients with ovarian cancer. Single Jurkat cells exhibited an extracellular acidification rate of 11 milli-pH min(-1), while primary T cells exhibited only 2 milli-pH min(-1). The polypeptide N-alpha-acetylgalactosaminyltransferases (ppGalNAcTs) play a key role in mucin-type O-linked glycan biosynthesis by installing the initial GalNAc residue on the protein scaffold. Haemophilus ducreyi is a Gram-negative bacterium that causes chancroid, a sexually transmitted disease. View details for DOI 10.1016/j.cell.2015.11.048, View details for PubMedCentralID PMC4715264. In nature, glycans are constructed by glycosyltransferases that are organized in an assembly line in the endoplasmic reticulum and Golgi compartment. As part of the quest for new gold drugs, we have explored the efficacy of three gold complexes derived from the tuberculosis drug pyrazinamide (PZA), namely, the gold(I) complex [Au(PPh3)(PZA)]OTf (1, OTf = trifluoromethanesulfonate) and two gold(III) complexes [Au(PZA)Cl2] (2) and [Au(PZO)Cl2] (3, PZO = pyrazinoic acid, the metabolic product of PZA) against two mycobacteria, Mycobacterium tuberculosis and Mycobacterium smegmatis. View details for Web of Science ID 000180171800015. New therapies are therefore needed to treat diseases caused by these organisms, and a better understanding of the mechanisms of envelope assembly should aid in their discovery. [4] Bertozzi is also an Investigator at the Howard Hughes Medical Institute (HHMI)[5] and is the former Director of the Molecular Foundry, a nanoscience research center at Lawrence Berkeley National Laboratory. 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. View details for DOI 10.1093/glycob/cwz045, View details for Web of Science ID 000493194700001. Conversely, unsialylated LacNAc glycans, enriched in the epithelial ducts, sequestered Gal-1 in the extracellular environment, ultimately attenuating invasive potential. Rabuka, D., Parthasarathy, R., Lee, G. S., Chen, X., Groves, J. T., Bertozzi, C. R. Vaccine efficacy of an attenuated but persistent Mycobacterium tuberculosis cysH mutant. A., Sletten, E. M., Baskin, J. M., Miller, I. Palaniappan, K. K., Pitcher, A. Upon exposure to mycobacterial cell wall lipids, 166 macrophage proteins showed differential expression. Of the sequence motifs that are associated with 4Fe-4S centers, the cysteine dyad is atypical and has generated discussion with respect to coordination as well as the cluster's larger functional significance. Human cells incubated with N-levulinoylmannosamine (ManLev) process this unnatural metabolic precursor into N-levulinoyl sialic acid (SiaLev), which is incorporated into cell surface glycoconjugates. The absence of activity on the trisaccharide Gal beta 1-->6Gal alpha-R indicates a requirement for a substrate with a terminal GlcNAc residue, suggesting that sulfation precedes further biosynthetic assembly of L-selection ligands. View details for Web of Science ID 000257629200046, View details for PubMedCentralID PMC2664610. View details for Web of Science ID 000264791600009, View details for PubMedCentralID PMC2657038. The azido sugars are then covalently tagged with imaging probes or epitope tags, either ex vivo or in vivo, using an azide-specific reaction. Herein, we report the first application of this glycoproteomic platform to human tissues cultured exvivo. Current approaches offer a precision approaching that of genetic control. Bhat, R., Belardi, B., Mori, H., Kuo, P., Tam, A., Hines, W. C., Quynh-Thu Le, Q. T., Bertozzi, C. R., Bissell, M. J. In addition, we solved the crystal structure of the Streptomyces coelicolor FGE homolog to 2.1 A resolution. From this global analysis, we have identified a subset of sulfur-metabolizing enzymes that are sensitive to multiple regulatory cues and may be strong candidates for therapeutic intervention. These results provide a guide for biologists in choosing a suitable ligation chemistry. In this protocol, we describe a novel mass-independent chemical glycoproteomics platform for characterizing intact, metabolically labeled glycopeptides from complex proteomes, termed Isotope Targeted Glycoproteomics (IsoTaG). Furthermore, perturbation of MMCoA metabolism attenuated pathogen replication in mice. A., Bertozzi, C. R. Extensive Determination of Glycan Heterogeneity Reveals an Unusual Abundance of High Mannose Glycans in Enriched Plasma Membranes of Human Embryonic Stem Cells. Chemical syntheses of uniform glycoproteins and polymeric glycoprotein mimics have facilitated the study of individual glycoconjugates in the absence of glycan microheterogeneity. The assay proceeds by transfer of 35S-labeled sulfate from [35S]-3(')-phosphoadenosine-5(')-phosphosulfate (PAPS) to the free amino groups of de-N-sulfated heparin (NDST-1), or the 6-hydroxyl groups of N-acetylglucosamine residues linked to a polyacrylamide scaffold (HEC-GlcNAc-6-ST). Yang, A. C., Stevens, M. Y., Chen, M. B., Lee, D. P., Stahli, D., Gate, D., Contrepois, K., Chen, W., Iram, T., Zhang, L., Vest, R. T., Chaney, A., Lehallier, B., Olsson, N., du Bois, H., Hsieh, R., Cropper, H. C., Berdnik, D., Li, L., Wang, E. Y., Traber, G. M., Bertozzi, C. R., Luo, J., Snyder, M. P., Elias, J. E., Quake, S. R., James, M. L., Wyss-Coray, T. Membrane-tethered mucin-like polypeptides sterically inhibit binding and slow fusion kinetics of influenza A virus. Taken together, these studies indicate that Rv2131c encodes a CysQ enzyme that may play a role in mycobacterial sulfur metabolism. Lim, H. C., Sher, J. W., Rodriguez-Rivera, F. P., Fumeaux, C. n., Bertozzi, C. R., Bernhardt, T. G. The mucin-selective protease StcE enables molecular and functional analysis of human cancer-associated mucins. [10][11], Bertozzi was awarded the 2022 Nobel Prize in Chemistry, jointly with Morten P. Meldal and Karl Barry Sharpless, "for the development of click chemistry and bioorthogonal chemistry". Glycosylation is an essential form of post-translational modification that regulates intracellular and extracellular processes. View details for DOI 10.1073/pnas.0403681101, View details for Web of Science ID 000225508400004, View details for PubMedCentralID PMC534710, View details for DOI 10.1074/jbc.M406397200, View details for Web of Science ID 000225229500103. WebThis years prize amount is 10 million Swedish kronor (about 920,000 U.S. dollars), to be shared equally between the three laureates. The structure of sialic acid on living cells can be modulated by metabolism of unnatural biosynthetic precursors. The average clinical sensitivity and specificity were 96% and 97%. The prokaryotic homolog exhibits remarkable structural similarity to human FGE, including the position of catalytic cysteine residues. Our methodology should provide general access to biochemical and imaging studies of cell surface proteins, using small fluorophores introduced via a short peptide tag. DMN-Tre labeling was detected within minutes and was inhibited by heat killing of mycobacteria. In an emerging strategy, glycans are imaged by metabolic labeling with chemical reporters and subsequent ligation to fluorescent probes. Exact mass measurements showed that S881 is highly unsaturated, tandem mass spectrometry indicated a polyisoprene-derived structure, and characterization of synthetic structural analogs confirmed that S881 is a previously undescribed sulfated derivative of dihydromenaquinone-9, the primary quinol electron carrier in M. tuberculosis. The assay was developed and validated in 7 distinct cohorts (n = 858) with the majority of the cohorts blinded prior to analysis. This may be a result of BPA sulfation/desulfation providing a pathway for selective uptake into hormone-responsive cells. Using azide-modified molecular precursors of sialic acids and copper-free click chemistry, we visualized the spatiotemporal dynamics of the sialome in live zebrafish embryos. Varki, A., Cummings, R. D., Esko, J. D., Freeze, H. H., Stanley, P., Marth, J. D., Bertozzi, C. R., Hart, G. W., Etzler, M. E. Control of the Molecular Orientation of Membrane-Anchored Biomimetic Glycopolymers. de Almeida, G., Townsend, L. C., Bertozzi, C. R. Mycobacterium tuberculosis Rv3406 Is a Type II Alkyl Sulfatase Capable of Sulfate Scavenging. and Shu Wang and Kim, {Hyun Jae} and Meyer, {Gerald J.} Polysialyltransferases catalyze the glycosylation of the neural cell adhesion molecule (NCAM) with polysialic acid (PSA). 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. Methods for the controlled derivatization of glycoproteins are presently limited by the repertoire of natural amino acid side chain and carbohydrate functionalities. 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