Little is known about how cells respond on a molecular level to tissue engineering scaffold materials. Chp1 is fully active in vitro, but in M. tuberculosis, its function is potentiated by the previously identified sulfolipid transporter MmpL8. View details for Web of Science ID 000222930600016. Here we report the facile synthesis of a difluorobenzocyclooctyne (DIFBO) that combines these modifications. View details for DOI 10.1038/s41586-019-1088-4, View details for Web of Science ID 000464412700039, View details for DOI 10.1073/pnas.1813020116, View details for Web of Science ID 000463936900024. Finally the lack of an endogenous human orthologue of cysH and its possible role in defence against adaptive immunity renders CysH an attractive enzyme for further studies as a target for therapeutics active against CTBI. This challenging process made her dream of This system thus constitutes an AND-type molecular logic gate that reports on the simultaneous presence of H(2)O(2) and caspase 8 activity. Using in situ Atomic Force Microscopy to investigate S-layer assembly on mica, we show this concept is equally valid during self-assembly of proteins into extended matrices. View details for Web of Science ID 000243895200017. Mycobacterium tuberculosis produces numerous exotic lipids that have been implicated as virulence determinants. A., Johnson, A. G., George, B. M., Majzoub, K., Villalta, P. W., Carette, J. E., Bertozzi, C. R. Synthetic Siglec-9 Agonists Inhibit Neutrophil Activation Associated with COVID-19, 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., Stanford COVID-19 Biobank. Sialylated glycans are found at elevated levels in many types of cancer and have been implicated in disease progression. L-Selectin, a receptor bearing a C-type lectin domain, mediates the initial attachment of lymphocytes to high endothelial venules of lymph nodes. We introduced the peptide sequence recognized by the endoplasmic reticulum (ER)-resident formylglycine generating enzyme (FGE), which can be as short as 6 residues, into heterologous proteins expressed in mammalian cells. Polysialyltransferases catalyze the glycosylation of the neural cell adhesion molecule (NCAM) with polysialic acid (PSA). Positioned at the C-terminus of many eukaryotic proteins, the glycosylphosphatidylinositol (GPI) anchor is a posttranslational modification that anchors the modified protein in the outer leaflet of the cell membrane. The advantage of this ELISA over previous assays is that a macromolecular physiological ligand is employed, rather than a fortuitous or simplified carbohydrate ligand. Tyrosine sulfation is a post-translational modification of many secreted and membrane-bound proteins. 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. In this report, genetic complementation using Escherichia coli mutant strains deficient in APS kinase and PAPS reductase was used to define the M. tuberculosis and Mycobacterium smegmatis CysH enzymes as APS reductases. Parthasarathy, R., Rabuka, D., Bertozzi, C. R., Groves, J. T. Copper-free click chemistry for dynamic in vivo imaging. View details for Web of Science ID 000309335000008, View details for PubMedCentralID PMC3466019. Kinetic studies revealed significant inhibitory activity and provide guidance for improved inhibitor design. These data provide strong evidence that Stf0 carries out the first committed step in the biosynthesis of SL-1 and establish a system for probing the role of SL-1 in M. tuberculosis infection. A broader theme that emerged was the urgent need to bring the glycosciences back into the mainstream of biology by integrating relevant education into the curricula of medical, graduate, and postgraduate training programs, thus generating a critical sustainable workforce that can advance the much-needed translation of glycosciences into a more complete understanding of biology and the enhanced practice of medicine. This enzyme transfers sialic acid residues from the host's sialylglycoconjugates to the parasite's galactosylglycoconjugates. Maturation is driven by the phosphoinositide kinase PIKfyve. This heterogeneity precludes enrichment strategies that can be universally beneficial for all glycan classes. View details for DOI 10.1016/j.celrep.2013.08.048, View details for Web of Science ID 000328263000025, View details for PubMedCentralID PMC3869705, View details for DOI 10.1371/journal.pone.0072304, View details for Web of Science ID 000323425700163. Other sulfonucleotide reductases from structurally divergent subclasses appear to use the same mechanism, suggesting that this family of enzymes has evolved from a common ancestor. 275, 21075-21080). In this study, we developed a crosslinking assay, utilizing bioorthogonal probes compatible with carrier protein modification, for probing the protein interactions between COM domains of NRPS enzymes. Furthermore, the method is found to be very specific, as after enrichment over 87% of all peptides contain (modified) azidohomoalanine. View details for DOI 10.1016/j.cub.2020.09.082. This strategy uses a two-step labeling procedure in which an unnatural sugar analogue containing a functional handle is (1) incorporated into sugar-bearing proteins via the cell's own biosynthetic machinery and then (2) detected with an exogenously added probe. Douglas, E. S., Chandra, R. A., Bertozzi, C. R., Mathies, R. A., Francis, M. B. Metabolic labeling of glycans with azido sugars and subsequent glycan-profiling and visualization via Staudinger ligation, Synthetic glycobiology: exploits in the Golgi compartment, Using phage display to select antibodies recognizing post-translational modifications independently of sequence context. We apply the strategy to a particularly redundant yet disease-relevant human glycosyltransferase family, the polypeptide N-acetylgalactosaminyl transferases. Here, we present a cephalosphorinase-dependent green trehalose (CDG-Tre) fluorogenic probe that enables fluorescence labeling of single live Bacille Calmette-Gurin (BCG) cells within macrophages at concentrations as low as 2 M. Our findings suggest that there is a dynamic and reciprocal link between integrin mechanosignalling and a bulky glycocalyx, implying a causal link towards a mesenchymal, stem-like phenotype in GBMs. A., Ge, Y. n., Gunawardena, J. n., Hendrickson, R. C., Hergenrother, P. J., Huber, C. G., Ivanov, A. R., Jensen, O. N., Jewett, M. C., Kelleher, N. L., Kiessling, L. L., Krogan, N. J., Larsen, M. R., Loo, J. This technique, which is described in detail, provides a direct measurement of the energy that is released nonradiatively following photostimulation, and can therefore be used to indirectly determine the amount of energy released via luminescent pathways. Moreover, we demonstrate the efficacy of PCL-1 for monitoring physiological fluctuations in H(2)O(2) levels by directly imaging elevations in H(2)O(2) within testosterone-stimulated tumor xenografts in vivo. Sequential assembly of the septal cell envelope prior to V snapping in Corynebacterium glutamicum. In addition, we generated a mutant M. tuberculosis strain lacking FGE. 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. Bertozzi developed a new type of reaction, now called a bioorthogonal reaction, that can occur in living environmentsrather than just in labswith no interference with other biochemical processes. View details for DOI 10.1073/pnas.0811481106, View details for Web of Science ID 000262263900006, View details for PubMedCentralID PMC2629201. We tested this prediction by investigating whether bulky glycoproteins in the glycocalyx promote a tumour phenotype in human cells by increasing integrin adhesion and signalling. In a prototypical experiment, a unique chemical motif, often as small as a single functional group, is incorporated into the target biomolecule using the cell's own biosynthetic machinery. In this work, we describe the synthesis and NMR characterization of four mono- and four dideoxygenated analogs of alpha,alpha-D-trehalose. This enhancement occurs upon metabolic conversion of DMN-Tre to trehalose monomycolate and incorporation into the mycomembrane of Actinobacteria. Since PSA is important in neural plasticity and development, this mechanism for modulating PSA structure might be useful for functional studies. Treatment of cells with the compounds abrogated mucin-type O-linked glycosylation but not N-linked glycosylation and also induced apoptosis. Fusion of these domains to the proteins FRB and FKBP enabled their induced assembly by the natural product rapamycin. In both leukocyte populations, the main proteins labeled were identified as different CD45 isoforms. On this Wikipedia the language links are at the top of the page across from the article title. View details for Web of Science ID 000172448800001. A functional domain of the M. tuberculosis CysC protein was cloned and expressed in E. coli, confirming the ability of this organism to make PAPS. We have coexpressed a human GST-5 cDNA with a GlyCAM-1/IgG fusion protein in COS-7 cells and observed four-fold enhanced [(35)S]sulfate incorporation into this mucin acceptor. The average overall agreement between ADAP and radioassay was above 91%. Front-line tuberculosis (TB) drugs have been characterized extensively invitro and invivo with respect to gene expression and cell viability. View details for Web of Science ID 000296756600001, View details for PubMedCentralID PMC3219546. 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. View details for Web of Science ID 000171601400045. Jolly, A. L., Agarwal, P., Metruccio, M. M., Spiciarich, D. R., Evans, D. J., Bertozzi, C. R., Fleiszig, S. M. Visualization of mycobacterial membrane dynamics in live cells. One of the most abundant is sulfolipid-1 (SL-1), a tetraacyl-sulfotrehalose glycolipid. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. These results shed light on the physical barriers that modulate phagocytosis, which have been heretofore underappreciated. A. Lee, J. H., Baker, T. J., Mahal, L. K., Zabner, J., Bertozzi, C. R., WIEMER, D. F., Welsh, M. J. Exploiting differences in sialoside expression for selective targeting of MRI contrast reagents. Hatzios, S. K., Iavarone, A. T., Bertozzi, C. R. Noncovalent cell surface engineering: Incorporation of bioactive synthetic glycopolymers into cellular membranes. Cyclopropanation of the mycobacterial cell wall glycolipid trehalose dimycolate is both required and sufficient to induce robust host angiogenesis. Using comprehensive identification of RNA-binding proteins by mass spectrometry (ChIRP-MS), we took an RNA-centric viewpoint of flaviviral infection and identified several hundred proteins associated with both DENV and ZIKV genomic RNA in human cells. While these lectins possess the ability to agglutinate A(1)-blood cells carrying the -GalNAc epitope and cross-link low valency glycoconjugates, only SBA showed a tendency to form intermolecular cross-links among the arrayed polyvalent mucin mimetics. Furthermore, their dynamic behavior in synthetic membranes mirrored that of natural biomolecules. 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. Wild world of bioorthogonal chemistry, Polymerization of glycosylated NCAs for preparation of biomedical materials and synthetic glycoproteins. View details for Web of Science ID 000168490400007, View details for Web of Science ID 000167717100191. Atoms out of Blobs: CryoEM Takes the Nobel Prize in Chemistry. A general method is described to sequester peptides containing azides from complex peptide mixtures, aimed at facilitating mass spectrometric analysis to study different aspects of proteome dynamics. View details for DOI 10.1016/j.ab.2005.02.004, View details for Web of Science ID 000229122600012. View details for DOI 10.1016/S0166-6851(03)00196-8, View details for Web of Science ID 000185793400002. 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. Cardiac myoblasts were also captured. This assembly inhibits L-, E-, and P-selectin binding to GlyCAM-1, a physiological ligand better than sLe(x)-like liposomes without additional anionic charge. Thus, new unbiased methods are needed to find PKMT substrates. [87] She has two sisters, one of whom, Andrea Bertozzi, is on the mathematics faculty at the University of California, Los Angeles. The synthesis of the azido sugars (ManNAz, GalNAz, GlcNAz or 6AzFuc) or detection reagents (phosphine-FLAG or phosphine-FLAG-His6) can be completed in approximately 1 week. Glycans can be imaged by metabolic labeling with azidosugars followed by chemical reaction with imaging probes; however, tissue-specific labeling is difficult to achieve. Using Mycobacterium marinum-infected zebrafish as a model, we identify the enzyme proximal cyclopropane synthase of alpha-mycolates (PcaA) as an important bacterial determinant of granuloma-associated angiogenesis. Finally, we showed that BNNTs can deliver DNA oligomers to the interior of cells with no apparent toxicity. Still, glycosylation remains the underexplored frontier of many biological systems. Glycosylation is an essential form of post-translational modification that regulates intracellular and extracellular processes. Delaveris, C. S., Webster, E. R., Banik, S. M., Boxer, S. G., Bertozzi, C. R. Introducing "In Focus", Community Resources Accelerating Science. A step in this direction will be the development of tools to identify metabolites that share common structural features. The glycosylation of serine and threonine residues with a single GlcNAc moiety is a dynamic posttranslational modification of many nuclear and cytoplasmic proteins. Here, we demonstrate that the conserved N-acetyglucosamine (GlcNAc) residues within chitobiose cores of N-glycans in the model organism Saccharomyces cerevisiae can be specifically targeted for metabolic replacement by unnatural sugars. To discover the molecular basis of this unusual role for a G protein, we biochemically characterized and solved the X-ray crystal structure of a complex between Pseudomonas syringae ATPS (CysD) and its associated regulatory G protein (CysN). We synthesized two unnatural oligosaccharide substrates, GlcNAc beta 1-->6Gal alpha-R and Gal beta 1-->4GlcNAc beta 1-->6Gal alpha-R, that incorporate structural motifs from the native L-selection ligands into an unnatural C-glycosyl hydrocarbon scaffold. This protocol outlines both the generation and the analysis of proteins aldehyde-tagged at their termini and the methods for chemical conjugation to the formylglycine. Members of the selectin family of adhesion receptors, consisting of L-, P- and E-selectin, mediate the initial interaction between leukocytes and endothelium during leukocyte trafficking from the blood into tissue sites. Studies of 4Fe-4S cluster stability and cysteine reactivity in the presence and absence of substrates, and in the free enzyme versus the covalent enzyme-intermediate (E-Cys-S-SO(3)(-)), suggest a structural rearrangement that occurs during the catalytic cycle. Kohler, J. J., Czlapinski, J. L., Laughlin, S. T., Schelle, M. W., de Graffenried, C. L., Bertozzi, C. R. Metabolic functionalization of recombinant glycoproteins. This data also suggested for a role of GALNT3 in aberrant EOC glycosylation, possibly implicated in disease progression. We report a chemical method in which the activity of an individual glycosyltransferase is controlled by a small molecule. Several anti-tuberculosis drugs target the biogenesis of this complex envelope, but their efficacy is declining due to resistance. The glycosylation reaction afforded the desired isomer exclusively and in good yield. Mauris, J., Mantelli, F., Woodward, A. M., Cao, Z., Bertozzi, C. R., Panjwani, N., Godula, K., Argueeso, P. Sulfatase-activated fluorophores for rapid discrimination of mycobacterial species and strains. We devised an experimental model that mimics the structure of mycobacterial envelopes in which an immobile hydrophobic layer supports a TDM-rich, two-dimensionally fluid leaflet. Hemmerich, S., Bertozzi, C. R., Leffler, H., ROSEN, S. D. FLUORESCENCE PROBES IN BIOCHEMISTRY - AN EXAMINATION OF THE NONFLUORESCENT BEHAVIOR OF DANSYLAMIDE BY PHOTOACOUSTIC CALORIMETRY. Calculated values of dissociation constants for the complexes indicate that AMP binds with a higher affinity to the enzyme intermediate than to the free enzyme. Detection and quantification of fatty acid fluxes in animal model systems following physiological, pathological, or pharmacological challenges is key to our understanding of complex metabolic networks as these macronutrients also activate transcription factors and modulate signaling cascades including insulin sensitivity. Here, we extend the IsoTaG approach with the use of alkynyl sugars as metabolic labels and employ new probes in analysis of the sialylated glycoproteome from PC-3 cells. Here we studied the function of novel germline variants in CSF3R at amino acid N610. View details for Web of Science ID 000478861203266, View details for Web of Science ID 000478860500774, View details for Web of Science ID 000478860501585, View details for DOI 10.1073/pnas.1818274116, View details for Web of Science ID 000461679000031. Seeliger, J. C., Topp, S., Sogi, K. M., Previti, M. L., Gallivan, J. P., Bertozzi, C. R. Thiacycloalkynes for Copper-Free Click Chemistry. Corrections? This gene was mapped to mouse chromosome X at band XA3.1-3.2. 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. Examples of sulfated metabolites as mediators of interactions between bacteria and plants suggest that sulfation is a key modulator of extracellular signaling between prokaryotes and eukaryotes. View details for DOI 10.1073/pnas.1322727111, View details for Web of Science ID 000334288600021. The modification modulates protein-protein interactions in the extracellular environment. Quantifying and controlling the orientation of surface-bound macromolecules is crucial to a wide range of processes in areas as diverse as biology, materials science, and nanotechnology. Most abundant is sulfolipid-1 ( SL-1 ), a receptor bearing a C-type domain... Chemistry, Polymerization of glycosylated NCAs for preparation of biomedical materials and synthetic glycoproteins exotic lipids that been. 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