Kramer, J., Zhou, M., Delaveris, C., Bertozzi, C. Antibody-enzyme conjugates for targeted glycocalyx editing, Synthesis of solvatochromic probes to label the mycobacterial cell wall and their use in studies of host-pathogen interactions. Front-line tuberculosis (TB) drugs have been characterized extensively invitro and invivo with respect to gene expression and cell viability. Sialic acid is a component of many tumor-associated oligosaccharide antigens. An inhibitor of the UDP-GlcNAc 4-epimerase that synthesizes UDP-GalNAc, the donor initiating O-linked glycosylation, would be a powerful reagent for reversibly inhibiting O-linked glycosylation. Several anti-tuberculosis drugs target the biogenesis of this complex envelope, but their efficacy is declining due to resistance. Antibodies bind to and agglutinate synthetic antigen-DNA conjugates, enabling ligation of the DNA strands and subsequent quantification by qPCR. Here, we report the identification of the SMK biosynthetic operon that, in addition to a previously identified sulfotransferase stf3, includes a putative cytochrome P450 gene (cyp128) and a gene of unknown function, rv2269c. Conjugated polymers capable of responding to external stimuli by changes in optical, electrical, or electrochemical properties can be used for the construction of direct sensing devices. Finally, the Delta papA2 and Delta papA1 mutants were screened for virulence defects in a mouse model of infection. A critical branch point in mucin-type oligosaccharides is the beta 1-->3 glycosidic linkage to the core alpha-N-acetylgalactosamine (GalNAc) residue. Three piperidine-melamine glycodendrimers were synthesized via a chemoenzymatic route and attached to human growth hormone and the Fc region of human IgG. Here, we show that increasing sialylated glycans on cancer cells inhibits human natural killer (NK) cell activation through the recruitment of sialic acid-binding immunoglobulin-like lectin 7 (Siglec-7). Rabuka, D., Rush, J. S., dehart, G. W., Wu, P., Bertozzi, C. R. Cellular Microfabrication: Observing Intercellular Interactions Using Lithographically-Defined DNA Capture Sequences. A genome-wide CRISPR screen identifies novel ligands for the Siglec family of glyco-immune checkpoint receptors. However, the specific glycoproteins that contribute to the cancer cell-surface sialylation are not well characterized, specifically in bona fide human disease tissue. These findings provide a platform for defining the molecular basis of SMK's role in M. tuberculosis pathogenesis. Douglas, E. S., Hsiao, S. C., Onoe, H., Bertozzi, C. R., Francis, M. B., Mathies, R. A. Synthesis and Microcontact Printing of Dual End-Functionalized Mucin-like Glycopolymers for Microarray Applications. The galectin family of glycan-binding proteins is thought to mediate many cellular processes by oligomerizing cell surface glycoproteins and glycolipids into higher-order aggregates. View details for Web of Science ID 000177962200018. We refer to these fascinating structures as "carbon nanohoops" due to their structural similarity to carbon nanotubes. However, a direct role for SL-1 in M. tuberculosis virulence has not been established. 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. Here, we sought to define if uncharacterized sialidases would provide distinct paradigms in sialic acid biochemistry. Jewett, J. C., Sletten, E. M., Bertozzi, C. R. Targeted metabolic labeling of yeast N-glycans with unnatural sugars. Hang, H. C., Yu, C., Kato, D. L., Bertozzi, C. R. Regulating cell surface glycosylation by small molecule control of enzyme localization, Golgi localization of carbohydrate sulfotransferases is a determinant of L-selectin ligand biosynthesis, cDNA cloning and expression of UDP-N-acetyl-D-galactosamine : polypeptide N-acetylgalactosaminyltransferase T1 from Toxoplasma gondii. The azido sugars are then covalently tagged with imaging probes or epitope tags, either ex vivo or in vivo, using an azide-specific reaction. 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. Mycobacterium tuberculosis synthesizes specific polyketide lipids that interact with the host and are required for virulence. Glycans are central to many biological processes, but efforts to define their functions at the molecular level have been frustrated by a lack of suitable technologies. Inhibition occurs through a metabolic mechanism in which ManBut is converted to unnatural sialic acid derivatives that effectively act as chain terminators during cellular PSA biosynthesis. View details for DOI 10.1074/mcp.M111.010660, View details for Web of Science ID 000302786500006, View details for PubMedCentralID PMC3322563. GPI-anchored proteins play vital roles in signal transduction, the vertebrate immune response, and the pathobiology of trypanosomal parasites. When evaluating mouse thymocytes and splenocytes as acceptors of the azido-sugar, a complex pattern of efficiently tagged glycoproteins was revealed. However, the mechanisms of impaired microglial homeostatic function and the cognitive effects of restoring this function remain unknown. 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. A., Bertozzi, C. R., Marahiel, M. A., Burkart, M. D. Uridine-Based Inhibitors as New Leads for Antibiotics Targeting Escherichia coli LpxC. Myoblast cells were patterned with high efficiency and remained undifferentiated after surface attachment. Stanford chemist Carolyn Bertozzi was awarded the Nobel Prize in chemistry for her development of bioorthogonal reactions, which allow scientists to explore cells and track biological processes without disrupting the normal chemistry of the cell. This story was updated on Wednesday, Oct. 6, at 1:23 p.m. PDT. Here we report the design, synthesis, and in vivo applications of Peroxy Caged Luciferin-1 (PCL-1), a chemoselective bioluminescent probe for the real-time detection of H(2)O(2) within living animals. Attachment via these "cell-adhesion barcodes" is rapid and specific, with close-packed arrays of cells forming within minutes. Palmitoylation is a widespread, reversible lipid modification that has been implicated in regulating a variety of cellular processes. Woods, E. C., Yee, N. A., Shen, J., Bertozzi, C. R. Glycocalyx Engineering with a Recycling Glycopolymer that Increases Cell Survival In Vivo. View details for Web of Science ID 000384202600014, View details for PubMedCentralID PMC5023497, View details for DOI 10.1021/acscentsci.5b00386, View details for PubMedCentralID PMC4827657. Here we show that MmpL8, a member of a large family of predicted lipid transporters in M. tuberculosis, is required for SL-1 production. Sequential assembly of the septal cell envelope prior to V snapping in Corynebacterium glutamicum. Song, J., Xu, J., Filion, T., Saiz, E., Tomsia, A. P., Lian, J. Moeckl, L., Pedram, K., Roy, A., Bertozzi, C., Moerner, W. Aebersold, R. n., Agar, J. N., Amster, I. J., Baker, M. S., Bertozzi, C. R., Boja, E. S., Costello, C. E., Cravatt, B. F., Fenselau, C. n., Garcia, B. We further developed a protein purification method that involves QC ligation of biotin to a protein of interest, capture on streptavidin resin, and finally release using only UV light. Here we report a method for rapid profiling of fucosylated glycoproteins from human cells using 6-azido fucose as a metabolic label. Taken together, these results demonstrate that the active site functionally communicates with the iron-sulfur cluster and also suggest a functional significance for the cysteine dyad in promoting site differentiation within the 4Fe-4S cluster. View details for DOI 10.1021/acs.jproteome.6b01053. Methods for site-specific protein conjugation are critical to such efforts. Azido sugars are fed to cells and integrated by the glycan biosynthetic machinery into various glycoconjugates. 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. 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. View details for DOI 10.1038/s41564-019-0518-2, View details for DOI 10.1158/1538-7445.AM2019-LB-109, View details for Web of Science ID 000488129900308, View details for DOI 10.1016/j.cell.2019.04.017, View details for Web of Science ID 000471256800016, View details for DOI 10.1021/acs.biochem.9b00170, View details for Web of Science ID 000468242400001. View details for DOI 10.1016/j.molcel.2020.03.030. Biomolecules labeled with azides can be detected through Cu-free click chemistry with cyclooctyne probes, but their intrinsic hydrophobicity can compromise bioavailability. The system was used to induce and repress heterologous protein overexpression reversibly, to create a conditional gene knockdown, and to control gene expression in a macrophage infection model. Such metabolic interference can block the expression of oligosaccharides or alter the structures of the sugars presented on cells. Zhu, X., Shieh, P., Su, M., Bertozzi, C. R., Zhang, W. A Bioorthogonal Reaction of N-Oxide and Boron Reagents. Moeckl, L., Pedram, K., Roy, A., Gustavsson, A., Bertozzi, C., Moerner, W. Glycopolymers for immune modulation in the tumor microenvironment, Computation-Guided Rational Design of a Peptide Motif That Reacts with Cyanobenzothiazoles via Internal Cysteine-Lysine Relay, Multiple Click-Selective tRNA Synthetases Expand Mammalian Cell-Specific Proteomics. Here, we describe the computation-guided rational design of a cysteine- and lysine-containing 11-residue peptide sequence that reacts with 2-cyanobenzothiazole (CBT) derivatives. Ligation of synthetic lipids with designed anchor structures to proteins was performed using native chemical ligation (NCL) of a C-terminal peptide thioester and an N-terminal cysteine lipid. A., Riley, L. W., Bertozzi, C. R. 5 '-Adenosinephosphosulphate reductase (CysH) protects Mycobacterium tuberculosis against free radicals during chronic infection phase in mice. These N610 substitutions were potently oncogenic and activated the receptor independently of its ligand GCSF. 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. These two strategies provide a means to selectively modify cell-surface glycans with exogenous probes. 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. Key to these findings was the use of glycopolymers end-functionalized with phospholipids, which enable the introduction of synthetically defined glycans onto cancer cell surfaces. The foundation focuses on curing NGLY1 deficiency through developing therapeutics that are efficient and inexpensive. Using high-performance liquid chromatography, we quantified the degree of accumulation and reversibility upon acidic compartment neutralization in macrophages and observed that accumulation was greater in infected than in uninfected macrophages. Carolyn R. Bertozzi is the 550th most popular chemist, the 15,732nd most popular biography from United States and the 111th most popular American Chemist. Because the parameters which govern this effect are well understood and are amenable to chemical modification, this knowledge may enable the rational development of more effective antibiotics against tuberculosis. Schumann, B., Debets, M., Wisnovsky, S., Agbay, A., Wagner, L., Choi, J., Gray, M., Bertozzi, C. Quantitative super-resolution microscopy reveals the architecture of the mammalian glycocalyx and its changes during cancer progression. Furthermore, many biological studies would be aided by the ability to assemble biomolecules under physiological conditions. Nessen, M. A., Kramer, G., Back, J., Baskin, J. M., Smeenk, L. E., de Koning, L. J., van Maarseveen, J. H., de Jong, L., Bertozzi, C. R., Hiemstra, H., de Koster, C. G. Direct Cell Surface Modification with DNA for the Capture of Primary Cells and the Investigation of Myotube Formation on Defined Patterns. However, controlled investigations of the relationships between glycosylation, rigidity, and extension of membrane-bound mucins or similar macromolecules are lacking, largely because of the absence of tractable experimental models. This complex could be stored as a lyophilized powder and then dissociated in organic solvents to produce free DIFBO for in situ kinetic and spectroscopic analysis. GlyCAM-1 was metabolically labeled in lymph node organ culture with 35SO4 and a panel of tritiated carbohydrate precursors. As this special issue testifies, the field of bioorthogonal chemistry is firmly established as a challenging frontier of reaction methodology and an important new instrument for biological discovery. Here, we report that metabolic cross-talk between the N-acetylgalactosamine salvage and O-GlcNAcylation pathways can be exploited for the tagging and identification of O-GlcNAcylated proteins. This approach should be applicable to any glycosyltransferase or group-transfer enzyme that tolerates unnatural azido substrates. The azidofluorescein derivative also enabled cell imaging under no-wash conditions with good signal above background. We used this method to identify interaction partners for the O-GlcNAc-modified FG-repeat nucleoporins. Consistent with an inverting mechanism, EnvSia156 reveals a His/Asp active center in which the His acts as a Brnsted acid and Asp as a Brnsted base in a single-displacement mechanism. WebAbout Carolyn's Work. Mycobacteria contain high levels of the disaccharide trehalose in free form as well as within various immunologically relevant glycolipids such as cord factor and sulfolipid-1. Chen, X., Wu, P., Rousseas, M., Okawa, D., Gartner, Z., Zettl, A., Bertozzi, C. R. DNA-barcode directed capture and electrochemical metabolic analysis of single mammalian cells on a microelectrode array. This Cu-free click reaction possesses comparable kinetics to the Cu-catalyzed reaction and proceeds within minutes on live cells with no apparent toxicity. WebCarolyn Ruth Bertozzi (born October 10, 1966) is an American chemist and Nobel laureate, known for her wide-ranging work spanning both chemistry and biology. With this technique, we studied the dynamics of glycan trafficking and identified a population of sialoglycoconjugates with unexpectedly rapid internalization kinetics. Sogi, K. M., Gartner, Z. J., Breidenbach, M. A., Appel, M. J., Schelle, M. W., Bertozzi, C. R. Self-Assembly of "S-Bilayers", a Step Toward Expanding the Dimensionality of S-Layer Assemblies. The design principles embodied in coumBARAC establish a platform for generating fluorogenic cyclooctynes suited for biological imaging. The mammalian glycocalyx is a heavily glycosylated extramembrane compartment found on nearly every cell. Here we present the design, preparation, and characterization of self-assembling functional bolaamphiphilic polydiacetylenes (BPDAs) inspired by nature's strategy for membrane stabilization. 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