View details for DOI 10.1073/pnas.2012196117. Comparison of these data to images of wild-type SbpA layers on intact cells gave insight into the interactions responsible for bilayer formation. View details for Web of Science ID 000227308100055. A., Bertozzi, C. R. Synthetic Trehalose Glycolipids Confer Desiccation Resistance to Supported Lipid Monolayers. We used the reaction for site-specific chemical modification of glyoxyl- and formylglycine-functionalized proteins, including an aldehyde-tagged variant of the therapeutic monoclonal antibody Herceptin. The resulting trehalose biosynthesis mutant was unable to proliferate and enter stationary phase unless supplemented with trehalose. Finally, we showed in a mouse model of infection that the loss of cyp128 exhibits a hypervirulent phenotype similar to that in previous studies of the stf3 mutant. Surprisingly, for three of the enzymes, significant activity was observed with sialylated LacNAc, and two of the enzymes were capable of detectable sulfation of GlcNAc in the context of sialyl Lewis x. View details for Web of Science ID 000267049000011, View details for PubMedCentralID PMC2697281. [27], Bertozzi also previously served on the research advisory board of several pharmaceutical companies including GlaxoSmithKline, and until recently Eli Lilly.[48]. (2001) Glycobiology 11, 11R-18R]. Bertozzi is the only female scientist to have been awarded a science Nobel prize this year, after an all-male line-up in 2021. Glycan structural diversity is directly correlated with difficulty in characterizing the intact glycoproteome by mass spectrometry (MS). The assay is suitable for high-throughout screening of compounds and may find use in the identification of selectin antagonists with anti-inflammatory potential. They originate from biosynthetic pathways comprising an assembly line of glycosyltransferases within the Golgi compartment. 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. Song, J., Xu, J., Filion, T., Saiz, E., Tomsia, A. P., Lian, J. Chidsey, C. E., Bertozzi, C. R., PUTVINSKI, T. M., Mujsce, A. M. Freeman Spogli Institute for International Studies, Institute for Computational and Mathematical Engineering (ICME), Institute for Human-Centered Artificial Intelligence (HAI), Institute for Stem Cell Biology and Regenerative Medicine, Stanford Institute for Economic Policy Research (SIEPR), Stanford Woods Institute for the Environment, Office of VP for University Human Resources, Office of Vice President for Business Affairs and Chief Financial Officer, Radiology - Rad/Molecular Imaging Program at Stanford, Maternal & Child Health Research Institute (MCHRI), aavelino@stanford.edu / gabbyg@stanford.edu, Directed Reading in Stem Cell Biology and Regenerative Medicine, Therapeutic Science at the Chemistry - Biology Interface, DOI 10.1146/annurev.biochem.71.110601.135334. Kinetic studies revealed significant inhibitory activity and provide guidance for improved inhibitor design. In the ligation reaction, the intermediate aza-ylide undergoes intramolecular reaction with an ester, forming an amide bond faster than aza-ylide hydrolysis would otherwise occur in water. Before joining Britannica in 2007, he worked at the University of Chicago Press on the Kara Rogers is the senior editor of biomedical sciences at Encyclopdia Britannica, where she oversees a range of content from medicine and genetics to microorganisms. Given the abilities of mycobacteria to survive desiccation and trehalose in solution to protect biomolecules and whole organisms during freezing, drying, and other stresses, we hypothesized that TDM alone may suffice to confer dehydration resistance to the membranes of which it is a constituent. 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. With their native proteinaceous backbones and natural glycosidic linkages, these agonists are attractive for translational applications. Wei, W., Riley, N. M., Yang, A. C., Kim, J. T., Terrell, S. M., Li, V. L., Garcia-Contreras, M., Bertozzi, C. R., Long, J. On this Wikipedia the language links are at the top of the page across from the article title. A., Bertozzi, C. R. Compositional profiling of heparin/heparan sulfate using mass spectrometry: assay for specificity of a novel extracellular human endosulfatase. 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. DMN-Tre labeling enabled the rapid, no-wash visualization of mycobacterial and corynebacterial species without nonspecific labeling of Gram-positive or Gram-negative bacteria. The isolation of this antibody signals the potential of phage antibody libraries in the derivation of reagents specific for post-translational modifications, although the extensive screening required indicates that such antibodies are extremely rare. 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. She completed her undergraduate degree in Chemistry from Harvard University in 1988 and her Ph.D. in Chemistry from UC Berkeley in 1993. The Staudinger ligation with alkyl azides was second-order overall and proceeded more rapidly in polar, protic solvents. First, we found that the W37I mutant of LplA catalyzes site-specific ligation of 10-azidodecanoic acid to LAP in cells, in nearly quantitative yield after 30 min. This tutorial review will summarize the history of this emerging field, as well as recent progress in the development and application of bioorthogonal copper-free click cycloaddition reactions. Glycosylation is a prevalent, yet heterogeneous modification with a broad range of implications in molecular biology. A chimera comprising the localization domain of GlcNAc6ST-1 fused to the catalytic domain of GlcNAc6ST-2 was confined to the trans-Golgi network and adopted the substrate preference of GlcNAc6ST-1. DNA origami protection and molecular interfacing through engineered sequence-defined peptoids. Moreover, these studies show that to properly exploit the sialic acid biosynthetic pathway for metabolic oligosaccharide engineering in H. ducreyi and possibly other prokaryotes that share similar pathways, precursors based on sialic acid and not mannosamine must be used. Proteins bearing this "aldehyde tag" were chemically modified by selective reaction with hydrazide- or aminooxy-functionalized reagents. Expression of the PknD substrate Rv0516c was highly induced by osmotic stress. The Staudinger ligation of azides and phosphines has found widespread use in the field of chemical biology, but the mechanism of the transformation has not been characterized in detail. Herein, we designed and synthesized the first chemically defined ligands for dectin-1 and dectin-2. 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. Interest in glycoproteomics continues to surge as MS instrumentation and software improve, so this review aims to help equip researchers with necessary information to choose appropriate enrichment strategies that best complement these efforts. Furthermore, the membrane-bound glycopolymers were internalized into early endosomes similarly to endogenous membrane components and were capable of specific interactions with protein receptors. We found that N-azidoacetylgalactosamine (GalNAz) is converted by endogenous mammalian biosynthetic enzymes to UDP-GalNAz and then epimerized to UDP-N-azidoacetylglucosamine (GlcNAz). We also exploited this finding to protect allogeneic and xenogeneic primary cells from NK-mediated killing, suggesting the potential of Siglecs as therapeutic targets in cell transplant therapy. GST-5 was also expressed in soluble epitope-tagged form and found to catalyze 6-O-sulfation of GlcNAc residues in synthetic acceptor structures. The simplicity and generality of this method make it well suited for use in the study of carbohydrate-mediated cell surface interactions. Senaratne, R. H., Mougous, J. D., Reader, J. R., Williams, S. J., Zhang, T., Bertozzi, C. R., Riley, L. W. Lipidomics reveals control of Mycobacterium tuberculosis virulence lipids via metabolic coupling. Here, we report a synergy between shape-generating processes in the cell interior and the external organization and composition of the cell-surface glycocalyx. APS reductase catalyzes the first committed step of reductive sulfate assimilation in pathogenic bacteria, including Mycobacterium tuberculosis, and is a promising target for drug development. In addition, we have redefined the substrate specificity of the B. subtilis CysH, formerly designated a PAPS reductase, as an APS reductase, based on its ability to complement a mutant E. coli strain deficient in APS kinase. Thus, despite its inherent advantages in sample collection, OF is not widely used for population screening. Given the sensitivity and negligible background provided by bioluminescence imaging (BLI), we reasoned that 1 might be able to overcome some of the limitations encountered with fluorescent phosphine probes. Once introduced into target biomolecules, either metabolically or through chemical modification, the azide can be tagged with probes using one of three highly selective reactions: the Staudinger ligation, the Cu(I)-catalyzed azide-alkyne cycloaddition, or the strain-promoted [3 + 2] cycloaddition. We probed the dynamic behavior of cell-bound glycopolymers bearing various hydrophobic anchors and glycan structures using fluorescence correlation spectroscopy (FCS). The chemical reporter is then covalently modified in a highly selective fashion with an exogenously delivered probe. It deftly subverts the bactericidal mechanisms of alveolar macrophages, ultimately inducing granuloma formation and establishing long-term residence in the host. 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. The structurally uniform alkyne-terminated mucin mimetic glycopolymers (see picture; TR = fluorophore) were printed on azide-functionalized chips by microcontact printing in the presence of a copper catalyst. A unique response factor (R) is determined for each disaccharide, whereas a multiplexed and data processing method is incorporated for faster data acquisition and quantification purposes. Corrections? However, a direct role for SL-1 in M. tuberculosis virulence has not been established. WebDr. 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. The omega-alkynyl-myristate and -palmitate analogs used with click chemistry and azido-probes will be invaluable to study protein acylation in vitro, in cells, and in vivo. Furthermore, we determined that the PAT biosynthetic machinery has no cross-talk with that for sulfolipid-1 despite their related structures. These findings elucidate a mechanism of age-related microglial impairment and a strategy to restore homeostasis in the ageing brain. We also found that malignant breast cells possess higher levels of nuclear Gal-1 and 2,6-SA and lower levels of LacNAc than nonmalignant cells in culture and in vivo and that nuclear localization of Gal-1 promotes a transformed phenotype. 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. The mobility of CD45 increased markedly upon engagement of Fc receptors. Although this phenomenon is well-established, little is known about the molecular-level interactions on which it depends. View details for DOI 10.1016/j.molcel.2020.03.030. In IsoTaG, metabolic labeling of the glycoproteome is combined with (i) chemical enrichment and isotopic recoding of glycopeptides to select peptides for targeted glycoproteomics using directed MS and (ii) mass-independent assignment of intact glycopeptides. Flynn, R. A., Belk, J. [86] Her maternal grandparents were from Nova Scotia, Canada. The original goal was to discuss the value of creating centers of excellence for training the next generation of biomedical investigators in the glycosciences. The ability to generate chemically defined analogues of GPI-anchored proteins is an important step toward elucidating the molecular functions of this interesting post-translational modification. Their involvement in inflammatory disease makes the selectins attractive targets for anti-inflammatory therapy. Tuberculosis (TB) is the leading cause of death from an infectious bacterial disease. She coined the term bioorthogonal chemistry to Beatty, K. E., Fisk, J. D., Smart, B. P., Lu, Y. Y., Szychowski, J., Hangauer, M. J., Baskin, J. M., Bertozzi, C. R., Tirrell, D. A. Bioluminescent Probes of Sulfatase Activity. Both significantly outperform EThcD methods, indicating that ETD-based methods are not required for routine N-glycoproteomics. Carolyn Bertozzi is the Anne T. and Robert M. Bass Professor of Chemistry and Professor of Chemical & Systems Biology and Radiology (by courtesy) at Stanford University, the Baker Family Director at Sarafan ChEM-H, and an Investigator of the Howard Hughes Medical Institute. Together, these studies show that two conserved sequence motifs, CCXXRKXXPL and SXGCXXCT, found in the C termini of all APS reductases, but not in PAPS reductases, may be used to predict the substrate specificity of these enzymes. 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. We treated worms with azidosugar variants of N-acetylglucosamine (GlcNAc), N-acetylgalactosamine (GalNAc), and N-acetylmannosamine (ManNAc), resulting in the metabolic labeling of their cell-surface glycans with azides. The 1,3-dipolar cycloaddition of cyclooctynes with azides, also called "copper-free click chemistry", is a bioorthogonal reaction with widespread applications in biological discovery. 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. She became an assistant professor at Berkeley in 1996 and a full professor of chemistry and molecular and cell biology in 2002. Bhakta, S., Bartes, A., Bowman, K. G., Kao, W. M., Polsky, I., Lee, J. K., Cook, B. N., Bruehl, R. E., ROSEN, S. D., Bertozzi, C. R., Hemmerich, S. New directions in glycoprotein engineering, Minimal sulfated carbohydrates for recognition by L-selectin and the MECA-79 antibody. View details for Web of Science ID 000167417700020. Furthermore, we developed a biomemetic coating strategy to interface BNNTs with proteins and cells. Fluorescent tagging in cultured cells and developing organisms has revealed important insights into the dynamics of these structures during growth and development. Cell surface glycans govern numerous cell-cell interactions are therefore key determinants of multicellular biology. We developed a series of ligand-inducible riboswitches that control gene expression in diverse species of Gram-negative and Gram-positive bacteria, including human pathogens that have few or no previously reported inducible expression systems. View details for DOI 10.1371/journal.pbio.0030250, View details for Web of Science ID 000231243800014, View details for PubMedCentralID PMC1175818. 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. The development of bioorthogonal reactions has classically focused on bond-forming ligation reactions. View details for DOI 10.1096/fj.07-9198com, View details for Web of Science ID 000254143700018, View details for PubMedCentralID PMC2865240. A., Bertozzi, C. R. Biomimetic bonelike composites and novel bioactive glass coatings. However, we were able to trap DIFBO by forming a stable inclusion complex with beta-cyclodextrin in aqueous media. [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. Using a high-throughput enzyme-linked lectin assay (ELLA), two inhibitors of murine ppGalNAcT-1 (K(I) approximately 8 microM) were identified that also inhibit several other members of the family. WebCarolyn Bertozzi (1966-ngin 10-ngiet 10-ngit ) he M-koet ke yit-chak fa-hok-k. Subsequently, the embryos were reacted with fluorophore conjugates by means of copper-free click chemistry, enabling the visualization of glycans in vivo at subcellular resolution during development. A. The properties of therapeutic proteins can be enhanced by chemical modification. Zhou, X., Rodriguez-Rivera, F. P., Lim, H., Bell, J. C., Bernhardt, T. G., Bertozzi, C. R., Theriot, J. 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 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. Little is known about the biosynthesis of PAT, although its biosynthetic gene cluster has been identified and found to resemble that of the better studied M. tuberculosis cell wall component sulfolipid-1. She described the reaction between the modified sugar and the fluorescent molecule as bioorthogonal. This system provides a platform to study cell-surface phenomena with a degree of chemical control that cannot be achieved using conventional biological tools. These data unambiguously establish the configuration of the resting enzyme metal center and, importantly, reveal the formation of a three-coordinate tris(thiolate) trigonal planar complex upon substrate binding as furthermore supported by density functional theory (DFT) calculations. The study of glycan function is a major frontier in biology that could benefit from small molecules capable of perturbing carbohydrate structures on cells. Delaveris, C. S., Wilk, A. J., Riley, N. M., Stark, J. C., Yang, S. S., Rogers, A. J., Ranganath, T., Nadeau, K. C., Blish, C. A., Bertozzi, C. R. Optimization of Metabolic Oligosaccharide Engineering with Ac4GalNAlk and Ac4GlcNAlk by an Engineered Pyrophosphorylase. Fcs ) of Fc receptors for routine N-glycoproteomics rapid, no-wash visualization of mycobacterial and corynebacterial without... By selective reaction with hydrazide- or aminooxy-functionalized reagents wild-type SbpA layers on intact cells gave into... 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