The acquisition of the sialyl residue allows the parasite to avoid lysis by serum factors and to interact with the host cell. View details for Web of Science ID 000296756600001, View details for PubMedCentralID PMC3219546. Glycans can be imaged by metabolic labeling with azidosugars followed by chemical reaction with imaging probes; however, tissue-specific labeling is difficult to achieve. ADAP detects zepto- to attomoles of antibodies in 2 L of sample with a dynamic range spanning 5-6 orders of magnitude. Metabolic and bioorthogonal labeling methods have previously enabled the enrichment and identification of sialoglycoproteins from cultured cells and model organisms. See vol 283, pg 4460, 2008). CalFluors: A Universal Motif for Fluorogenic Azide Probes across the Visible Spectrum. This review discusses the structural diversity of the GPI anchor and its putative cellular functions, including involvement in lipid raft partitioning, signal transduction, targeting to the apical membrane, and prion disease pathogenesis. Our optimized two-step enzymatic/chemical labeling scheme was used to tag and image a variety of LAP fusion proteins in multiple mammalian cell lines with diverse fluorophores including fluorescein, rhodamine, Alexa Fluor 568, ATTO 647N, and ATTO 655. Hatzios, S. K., Schelle, M. W., Newton, G. L., Sogi, K. M., Holsclaw, C. M., Fahey, R. C., Bertozzi, C. R. Isotopic Signature Transfer and Mass Pattern Prediction (IsoStamp): An Enabling Technique for Chemically-Directed Proteomics. The leukocyte adhesion molecule L-selectin mediates lymphocyte homing to secondary lymphoid organs and to certain sites of inflammation. We report here a study of mycomembrane dynamics that was enabled by trehalose-fluorophore conjugates capable of labeling trehalose glycolipids in live actinomycetes. View details for DOI 10.1073/pnas.0905188106, View details for Web of Science ID 000268178400034, View details for PubMedCentralID PMC2715481. The properties of therapeutic proteins can be enhanced by chemical modification. Most identified proteins were involved in mechanisms of cellular metabolic functions, post-translational modifications, and some have been reported to be implicated in EOC etiology. Identification of new components of the RipC-FtsEX cell separation pathway of Corynebacterineae. We designed synthetically tractable glycosylated polymers that possess rodlike extended conformations similar to natural mucins. One such metabolite from M. tuberculosis lipid extracts, S881, has been shown to negatively regulate the virulence of M. tuberculosis in mouse infection studies, and its cell-surface localization suggests a role in modulating host-pathogen interactions. In the present study, we expressed Rv2131c heterologously and found that the protein dephosphorylates PAP in a magnesium-dependent manner, with optimal activity observed between pH 8.5 and pH 9.5 using 0.5 mM MgCl 2. Finally, we engineered the Golgi-resident glycosyltransferase FucT7 for tunable control by Tmp-SLF in mammalian cells. Onoe, H., Hsiao, S. C., Douglas, E. S., Gartner, Z. J., Bertozzi, C. R., Francis, M. B., Mathies, R. A. Sulfolipid-1 Biosynthesis Restricts Mycobacterium tuberculosis Growth in Human Macrophages. Kehoe, J. W., Velappan, N., Walbolt, M., Rasmussen, J., King, D., Lou, J., Knopp, K., Pavlik, P., Marks, J. D., Bertozzi, C. R., Bradbury, A. R. Substrate recognition, protein dynamics, and iron-sulfur cluster in Pseudomonas aeruginosa adenosine 5 '-phosphosulfate reductase. Riley, N. M., Lu, L., Shortreed, M. R., Smith, L. M., Bertozzi, C. R. Dissecting O-GalNAc glycosylation by glycosyltransferase engineering. Baranov, M. V., Bianchi, F., Schirmacher, A., van Aart, M. A., Maassen, S., Muntjewerff, E. M., Dingjan, I., Ter Beest, M., Verdoes, M., Keyser, S. G., Bertozzi, C. R., Diederichsen, U., van den Bogaart, G. Making Glycoproteomics via Mass Spectrometry More Accessible to the greater Scientific Community. The critical reagent, a substituted cyclooctyne, possesses ring strain and electron-withdrawing fluorine substituents that together promote the [3 + 2] dipolar cycloaddition with azides installed metabolically into biomolecules. Thus, cell surface ketones are a potential vehicle for a metabolically controlled small-molecule drug delivery system. Drawing on these results, we analyzed the relationship between alkyne bond angles, which we determined using X-ray crystallography, and reactivity, quantified by experimental second-order rate constants, for a range of cyclooctynes. View details for Web of Science ID 000245946400051, View details for PubMedCentralID PMC2535821. Methods for the controlled derivatization of glycoproteins are presently limited by the repertoire of natural amino acid side chain and carbohydrate functionalities. Together, these data reveal a mechanism by which PcaA-mediated cis-cyclopropanation of mycolic acids promotes bacterial growth and dissemination invivo by eliciting granuloma vascularization and suggest potential approaches for host-directed therapies. Metabolic labeling can identify recently synthesized glycans and thus directly track glycan dynamics. In the measurement, we add 50-nm-diameter superparamagnetic magnetite particles, coated with antibodies, to an aqueous sample containing L. monocytogenes. A total of 589 differentially expressed glycoproteins were identified upon GALNT3 KD. Here we report a method for rapid profiling of fucosylated glycoproteins from human cells using 6-azido fucose as a metabolic label. However, the copper catalysts are too cytotoxic for long-term exposure with live cells or organisms. Metabolic labeling of glycans with a bioorthogonal chemical reporter such as the azide enables their visualization in cells and organisms as well as the enrichment of specific glycoprotein types for proteomic analysis. The cells' spatial arrangements and interconnectivities, both critical elements of higher-order function, derive from complex developmental programs in vivo and are often difficult or impossible to emulate in vitro. Herein, we use metabolic labeling methods to visualize the effects of TB drugs on cell envelope dynamics in mycobacterial species. Finally, mechanistic and structural data from sulfate-assimilation enzymes have revealed how M. tb controls the flux of sulfate in the cell. The widespread role of sulfotransferases in modulating glycan function makes them prime targets for small-molecule modulators. View details for DOI 10.1021/jacs.6b03861, View details for PubMedCentralID PMC5327792, View details for DOI 10.1021/acscentsci.6b00224, View details for PubMedCentralID PMC4999963. Our glycan-specific assay can be paired with traditional proximity ligation assays to simultaneously determine the change in total protein levels. The glycosylphosphatidylinositol (GPI) anchor is a C-terminal posttranslational modification found on many eukaryotic proteins that reside in the outer leaflet of the cell membrane. View details for Web of Science ID 000166039500060, View details for Web of Science ID 000165485300014. The repertoire of sialic acids presented by cells can be expanded to include unnatural variants by intercepting the sialic acid biosynthetic pathway with unnatural precursors. ESI-FTICR MS was utilized to characterize a 4Fe-4S containing protein Mycobacterium tuberculosis APS reductase. WebCarolyn Bertozzi (1966-ngin 10-ngiet 10-ngit ) he M-koet ke yit-chak fa-hok-k. [reaction: see text] Nearly all known sulfatases share a common active site modification that is required for their activity: conversion of cysteine to alpha-formylglycine. Previous structural analysis of the oligosaccharide chains on GlyCAM-1, an endothelial-derived ligand for L-selectin, revealed two novel structures: 6'-sulfo sialyl Lewis x and 6-sulfo sialyl Lewis x. View details for DOI 10.1096/fj.07-9198com, View details for Web of Science ID 000254143700018, View details for PubMedCentralID PMC2865240. The deep structural analysis enabled by this new method will enable future mechanistic studies on the biological significance of high mannose glycans on stem cell membranes and provide a general tool to examine cell surface glycosylation. Carolyn Bertozzi, a Stanford professor and serial biotech founder, has been awarded this years Nobel Prize in chemistry along with two other scientists, the Royal Swedish Academy of Sciences announced Wednesday.. She shares her prize with Morten Meldal, of the University of Copenhagen in Denmark, and K. Barry Sharpless, a former The mobility of CD45 increased markedly upon engagement of Fc receptors. In this paper, an efficient enzyme kinetics assay for Stf0 using electrospray ionization (ESI) mass spectrometry is presented. [16], Bertozzi completed her Ph.D. in chemistry at University of California, Berkeley in 1993 with Mark Bednarski, working on the chemical synthesis of oligosaccharide analogs. View details for DOI 10.1007/s00216-016-9934-9, View details for Web of Science ID 000391364200021. She completed her undergraduate degree in Chemistry from Harvard University in 1988 and her Ph.D. in Chemistry from UC Berkeley in 1993. Though not directly subject to mutation, we can determine glycan structure-function relationships by synthesizing defined glycoconjugates or by altering natural glycosylation pathways. Selective protein-protein interactions between nonribosomal peptide synthetase (NRPS) proteins, governed by communication-mediating (COM) domains, are responsible for proper translocation of biosynthetic intermediates to produce the natural product. 1-68A and a 2-dehydroxy analogue, 1-68Aa, inhibit several purified LpxC orthologues. Here, we report a method that combines the metabolic incorporation of a cyclooctyne-functionalized sialic acid derivative with a ligation reaction of a fluorogenic tetrazine, allowing for the imaging of sialylated glycoconjugates within live zebrafish embryos. Notably, the reaction of azides with terminal alkynes can be accelerated dramatically by copper catalysis (this highly popular Cu-catalyzed azide-alkyne cycloaddition (CuAAC) is a quintessential "click" reaction). This may be a result of BPA sulfation/desulfation providing a pathway for selective uptake into hormone-responsive cells. and Shu Wang and Kim, {Hyun Jae} and Meyer, {Gerald J.} New additions to the bioorthogonal chemistry compendium can advance biological research by enabling multiplexed analysis of biomolecules in complex systems. 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. We developed a polymer coating for carbon nanotubes (CNTs) that mimics the mucin glycoprotein coating of mammalian cells. 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. 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. Proteasome inhibitors are used to treat blood cancers such as multiple myeloma (MM) and mantle cell lymphoma. Our findings indicate that glycan valency can set thresholds for cross-linking by lectins. Paulick, M. G., Forstner, M. B., Groves, J. T., Bertozzi, C. R. Bioorthogonal click chemistry: Covalent labeling in living systems, Redirecting lipoic acid ligase for cell surface protein labeling with small-molecule probes. Therefore, sulfation may increase the estrogenic potential of xenobiotics. WebBertozzi is a professor of Humanities and Sciences, and of Chemical and Systems Biology and of Radiology. These N610 substitutions were potently oncogenic and activated the receptor independently of its ligand GCSF. This technique has been exploited in fundamental studies of glycan-dependent cell-cell and virus-cell interactions and also provides an avenue for the chemical remodelling of living cells. The L-selection ligands on lymph mode HEVs are mucin-like glycoproteins adorned with the unusual sulfated carbohydrate epitope, 6-sulfo sialyl Lewis x. Sulfation of this epitope on the N-acetylglucosamine (GlcNAc) residue confers high-avidity L-selection binding, and is thought to be restricted in the vasculature to sites of sustained lymphocyte recruitment. Natural mucins are densely glycosylated O-linked glycoproteins that serve numerous functions on cell surfaces. For her groundbreaking contributions to click chemistry and bioorthogonal chemistry, Bertozzi was awarded the 2022 Nobel Prize for Chemistry, which she shared with American chemist K. Barry Sharpless and Danish chemist Morten P. Meldal. Bertozzi holds the Anne T. and Robert M. Bass Professorship in the School of Humanities and Sciences at Stanford University. Thus, subtle structural differences in PSA resulting from the incorporation of SiaProp residues do not alter the antiadhesive properties of polysialylated NCAM. The cysH mutant was also susceptible to peroxynitrite and hydrogen peroxide in vitro. Bacteria are able to adapt to dramatically different microenvironments, but in many organisms, the signaling pathways, transcriptional programs, and downstream physiological changes involved in adaptation are not well-understood. View details for Web of Science ID 000180171800015. Here, we report the development of a nanoscale cell injection system (termed the nanoinjector) that uses carbon nanotubes to deliver cargo into cells. This protocol details the syntheses of the azido sugars N-azidoacetylmannosamine (ManNAz), N-azidoacetylgalactosamine (GalNAz), N-azidoacetylglucosamine (GlcNAz) and 6-azidofucose (6AzFuc), and the detection reagents phosphine-FLAG and phosphine-FLAG-His6. 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. Methods capable of directing orientation, as well as an understanding of the underlying physical mechanisms are, however, lacking. View details for Web of Science ID 000082564500003. Notably, PapA3 was selective for trehalose; no activity was observed with other structurally related disaccharides. We demonstrate that cyp128 and stf3 are sufficient for the biosynthesis of SMK from menaquinone and rv2269c exhibits promoter activity in M. tuberculosis. View details for DOI 10.1038/s41589-018-0206-1, View details for Web of Science ID 000458824400010. Individual GalNAc-Ts were rationally engineered to contain an enlarged active site (hole) and probed with a newly synthesized collection of 20 (bumped) uridine diphosphate N-acetylgalactosamine (UDP-GalNAc) analogs to identify enzyme-substrate pairs that retain peptide specificities but are otherwise completely orthogonal to native enzyme-substrate pairs. View details for Web of Science ID 000171204900005. Yap, M. C., Kostiuk, M. A., Martin, D. D., Perinpanayagam, M. A., Hak, P. G., Siddam, A., Majjigapu, J. R., Rajaiah, G., Keller, B. O., Prescher, J. Stanford University biochemist Carolyn Bertozzi is a highly admired scientist, entrepreneur, and advocate for diversity, particularly for LGBTQ+ people. We also demonstrate that 15 proteins undergo post-translational myristoylation in apoptotic Jurkat T cells. Welch Award in Chemistry (2022); The Dickson Prize in Medicine, University of Pittsburgh (2022); Dr H.P. Progress in the identification and characterization of myristoylated proteins has been impeded by the long exposure times required to monitor incorporation of radioactive myristate into proteins (typically 1-3 months). This review highlights changes in glycosylation associated with cancer and chronic inflammation and new therapeutic and diagnostic strategies that are based on the underlying glycobiology. Studies showed that a bulky glycocalyx potentiates integrin mechanosignalling and tissue tension and promotes a mesenchymal, stem-like phenotype in GBMs. This enhancement occurs upon metabolic conversion of DMN-Tre to trehalose monomycolate and incorporation into the mycomembrane of Actinobacteria. In addition, GalNAz efficiently labeled mucin-type O-linked glycoproteins expressed at endogenous levels. The lack of a defined consensus sequence for the ppGalNAcTs makes the prediction of mucin-type O-linked glycosylation difficult based on primary sequence alone. Abnormalities in the synthesis or presentation of these carbohydrates can lead to misfolded and inactive proteins, as well as to several debilitating disease states. In this report, we seek to expand the functional repertoire of such transformations by introducing a new bond-cleaving reaction between N-oxide and boron reagents. Agarwal, P., van der Weijden, J., Sletten, E. M., Rabuka, D., Bertozzi, C. R. Real-Time Noninvasive Imaging of Fatty Acid Uptake in Vivo. Sulfurcontaining molecules were initially identified by mass spectral analysis of cell extracts from bacteria labeled metabolically with a stable sulfur isotope (34SO 4 2-). Importantly, we detected increased PDIM synthesis in bacteria growing within host tissues and in bacteria grown in culture on odd-chain fatty acids. View details for DOI 10.1073/pnas.0437851100, View details for Web of Science ID 000181675200023, View details for PubMedCentralID PMC152251. Recent advances in our understanding of SL-1 biosynthesis will help elucidate the role of this curious metabolite in M. tb infection. A library of potential bisubstrate analogue inhibitors (1) targeting sulfotransferase enzymes was generated by the chemoselective ligation of the PAPS mimic 2 with a panel of 447 aldehydes. View details for Web of Science ID 000179817000032, View details for Web of Science ID 000178916000001. View details for Web of Science ID 000171601400045. View details for Web of Science ID 000227308100055. A., Bertozzi, C. R. Chemoselective ligation applied to the synthesis of a biantennary N-linked glycoform of CD52, MmpL8 is required for sulfolipid-1 biosynthesis and Mycobacterium tuberculosis virulence. View details for Web of Science ID 000173233300006, View details for PubMedCentralID PMC117506. The location of the surface-anchored TS resulted too far off as to be capable to sialylate mucins, a role played by the shed TS instead. Here we report that a bulky glycocalyx promotes the expansion of disseminated tumor cells in vivo by fostering integrin adhesion assembly to permit G1 cell cycle progression. View details for Web of Science ID 000222930600016. We developed a novel universal MHC class II presentation assay based on a bio-orthogonal "clickable" antigen and showed that MHC class II presentation was disrupted by the inhibition of PIKfyve, which in turn resulted in reduced activation of CD4+ Tcells. Sulfated constituents of GlyCAM-1 were identified as Gal-6-SO4, GlcNAc-6-SO4, (SO4-6)Gal beta 1-->4GlcNAc, and Gal beta 1-->4(SO4-6)GlcNAc. K chhai 2022-ngin tet-to Nobel Fa-hok Ching . Metabolic labeling of glycans with synthetic sugar analogs has emerged as an attractive means for introducing nonnatural chemical functionality into glycoproteins. View details for Web of Science ID 000294081900008. 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. CNTs coated with these mucin mimic polymers have two novel properties: they can bind to carbohydrate receptors, providing a means for biomimetic interactions with cell surfaces, and, importantly, they are rendered nontoxic to cells. 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). Applying IsoStamp, we were able to detect femtomole quantities of a single tagged protein from total mammalian cell lysates at signal-to-noise ratios as low as 2.5:1. Marcaurelle, L. A., SHIN, Y. S., Goon, S., Bertozzi, C. R. Sampson, N. S., Mrksich, M., Bertozzi, C. R. Substrate specificity of the sialic acid biosynthetic pathway. The first synthesis and characterization of [9]-, [12]-, and [18]cycloparaphenylene was demonstrated utilizing a novel aromatization reaction. Low molecular weight and singly charged fragments, obtained by a combination of gel filtration and anion-exchange chromatography, were analyzed. In this study we demonstrate that polysialyltransferases are capable of accepting unnatural substrates in terminally differentiated human neurons. Furthermore, we show that the biosynthesis of S881 relies on the universal sulfate donor 3'-phosphoadenosine-5'-phosphosulfate and a previously uncharacterized sulfotransferase, stf3. The glycosylated polymers were end-functionalized with lipid groups and embedded into supported lipid bilayers where they interact with protein receptors in a structure-dependent manner. The recently described O-glycoprotease OpeRATOR presents exciting opportunities for O-glycoproteomics. View details for Web of Science ID 000250428200015. For N-glycopeptides, HCD and sceHCD generate similar numbers of identifications, although sceHCD generally provides higher quality spectra. Carroll, K. S., Gao, H., Chen, H. Y., Stout, C. D., Leary, J. These results shed light on the physical barriers that modulate phagocytosis, which have been heretofore underappreciated. Protein glycosylation is widely recognized as a modulator of protein structure, localization, and cell-cell recognition in multicellular systems. The sulfate assimilation pathway of Mtb produces a number of sulfur-containing metabolites with important contributions to pathogenesis and survival. Glioblastoma multiforme (GBMs) are recurrent lethal brain tumours. This left Bertozzi and the rest of the lab to complete their Ph.D. work with no direct supervision. Analysis of truncation mutants demonstrated that perturbation of the stem region of GlcNAc6ST-1 affects the cellular substrate preference of the enzyme without altering its retention within the Golgi. We designed a 4-N,N-dimethylamino-1,8-naphthalimide-conjugated trehalose (DMN-Tre) probe that undergoes >700-fold increase in fluorescence intensity when transitioned from aqueous to hydrophobic environments. Sheta, R., Roux-Dalvai, F., Woo, C. M., Fournier, F., Bourassa, S., Bertozzi, C. R., Droit, A., Bachvarov, D. Glyco-seek: Ultrasensitive Detection of Protein-Specific Glycosylation by Proximity Ligation Polymerase Chain Reaction. Here we describe a method for targeting select proteins by chemical modification with a tag that imparts a distinct isotopic signature detectable in a full-scan mass spectrum. In these sulfur auxotrophs, heavy sulfate is channeled exclusively into sulfated metabolites. View details for DOI 10.1073/pnas.0307128101, View details for Web of Science ID 000187937200026, View details for PubMedCentralID PMC314150, View details for DOI 10.1002/anie.200352673, View details for Web of Science ID 000220266000010, View details for DOI 10.1002/anie.200454235, View details for Web of Science ID 000224592400009, View details for DOI 10.1002/anie.200460620, View details for Web of Science ID 000225445200005, View details for Web of Science ID 000223490500010. Here, we report a synergy between shape-generating processes in the cell interior and the external organization and composition of the cell-surface glycocalyx. Bertozzi received a bachelors degree in chemistry from Harvard University in 1988 and a doctorate in the same subject from the University of California, Berkeley in 1993. And thus directly track glycan dynamics mammalian cells completed her undergraduate degree in Chemistry from University... 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