Seeliger, J. C., Holsclaw, C. M., Schelle, M. W., Botyanszki, Z., Gilmore, S. A., Tully, S. E., Niederweis, M., Cravatt, B. F., Leary, J. Sulfotyrosine is a post-translational modification important in many extracellular protein-protein interactions, including human immunodeficiency virus infection. Woods, E. C., Kai, F., Barnes, J., Pedram, K., Pickup, M. W., Hollander, M. J., Weaver, V. M., Bertozzi, C. R. Exploring the role of Nrf1 in NGly1 deficiency. Work in our laboratory led to the development of two bioorthogonal transformations that exploit the azide as a small, abiotic, and bioinert reaction partner: the Staudinger ligation and strain-promoted azide-alkyne cycloaddition. A genome-wide CRISPR screen identifies novel ligands for the Siglec family of glyco-immune checkpoint receptors. Click chemistry and bio-orthogonal chemistry. Wan, S. J., Sullivan, A. Ngo, J. T., Adams, S. R., Deerinck, T. J., Boassa, D., Rodriguez-Rivera, F., Palida, S. F., Bertozzi, C. R., Ellisman, M. H., Tsien, R. Y. The identification of certain cell surface oligosaccharides as potent antigens has prompted their use in tumor vaccines, and inspired new approaches to the management of tissue rejection subsequent to xenotransplantation. View details for DOI 10.1074/jbc.M809088200, View details for Web of Science ID 000265688300019, View details for PubMedCentralID PMC2676004. Cell surfaces are endowed with biological functionality designed to mediate extracellular communication. Biological analysis of diptericin fragments indicated that the main determinant of antibacterial activity lay in the C-terminal region that is similar to the attacin peptides, although the N-terminal segment, related to the proline-rich family of antibacterial peptides, augmented that activity by 100-fold. Proof of principle was performed by using various heparin/HS samples isolated from bovine and porcine tissues. Sialylated glycans are found at elevated levels in many types of cancer and have been implicated in disease progression. These compounds may provide new scaffolds for extension of existing LpxC-inhibiting antibiotics to target the UDP binding pocket. Z. Multi-omics analysis of spatially distinct stromal cells reveals tumor-induced O-glycosylation of the CDK4-pRB axis in fibroblasts at the invasive tumor edge. Laughlin, S. T., Baskin, J. M., Amacher, S. L., Bertozzi, C. R. Rapid detection, discovery, and identification of post-translationally myristoylated proteins during apoptosis using a bio-orthogonal azidomyristate analog. a nanoscience research center at Lawrence Berkeley National Laboratory. Patterson, B. n., Dinkele, R. n., Gessner, S. n., Morrow, C. n., Kamariza, M. n., Bertozzi, C. R., Kamholz, A. n., Bryden, W. n., Call, C. n., Warner, D. F., Wood, R. n. Marschallinger, J. n., Iram, T. n., Zardeneta, M. n., Lee, S. E., Lehallier, B. n., Haney, M. S., Pluvinage, J. V., Mathur, V. n., Hahn, O. n., Morgens, D. W., Kim, J. n., Tevini, J. n., Felder, T. K., Wolinski, H. n., Bertozzi, C. R., Bassik, M. C., Aigner, L. n., Wyss-Coray, T. n. Updates to the Symbol Nomenclature for Glycans guidelines, Neelamegham, S., Aoki-Kinoshita, K., Bolton, E., Frank, M., Lisacek, F., Luetteke, T., O'Boyle, N., Packer, N. H., Stanley, P., Toukach, P., Varki, A., Woods, R. J., Darvill, A., Dell, A., Henrissat, B., Bertozzi, C., Hart, G., Narimatsu, H., Freeze, H., Yamada, I., Paulson, J., Prestegard, J., Marth, J., Vliegenthart, J. G., Etzler, M., Aebi, M., Kanehisa, M., Taniguchi, N., Edwards, N., Rudd, P., Seeberger, P., Mazumder, R., Ranzinger, R., Cummings, R., Schnaar, R., Perez, S., Kornfeld, S., Kinoshita, T., York, W., Knirel, Y., SNFG Discussion Grp, Engineering Orthogonal Polypeptide GalNAc-Transferase and UDP-Sugar Pairs. Expression of large tumour-associated glycoproteins in non-transformed mammary cells promoted focal adhesion assembly and facilitated integrin-dependent growth factor signalling to support cell growth and survival. Chung, S., Shin, S., Bertozzi, C. R., De Yoreo, J. J. Difluorobenzocyclooctyne: Synthesis, Reactivity, and Stabilization by beta-Cyclodextrin. Together, glycomic and metabolic labeling techniques provide a comprehensive description of glycosylation as a foundation for hypothesis generation. Furthermore, the study of SL-1 has led to questions regarding the significance of sulfation in mycobacteria. Furthermore, many biological studies would be aided by the ability to assemble biomolecules under physiological conditions. Author Correction: Lipid-droplet-accumulating microglia represent a dysfunctional and proinflammatory state in the aging brain. View details for DOI 10.1073/pnas.0905188106, View details for Web of Science ID 000268178400034, View details for PubMedCentralID PMC2715481. The emergence of drug-resistant Mycobacterium tuberculosis strains and the widespread occurrence of AIDS demand newer and more efficient control of tuberculosis. Jain, M., Petzold, C. J., Schelle, M. W., Leavell, M. D., Mougous, J. D., Bertozzi, C. R., Leary, J. We frame central issues regarding determination of protein-level variation and PTMs, including some paradoxes present in the field today. Despite this wealth of disease-relevant targets, there are currently few effective pharmacological tools to interfere with protein palmitoylation. Carolyn earned A. Sequential assembly of the septal cell envelope prior to V snapping in Corynebacterium glutamicum. This approach can highlight changes in physiology or environment and may be more informative than steady-state analyses. Investigators have developed tools including small molecule inhibitors, decoy substrates, and engineered proteins to modify cellular glycans. Recent progress in identifying and analyzing physiological selectin counter-receptors suggests new approaches to the design of ligands that bind to specific selectins. The unnatural sialic acid analog, N-levulinoyl sialic acid (SiaLev), was incorporated into cell surface glycoconjugates including PSA by the incubation of cultured neurons with the metabolic precursor N-levulinoylmannosamine (ManLev). The advantage of this ELISA over previous assays is that a macromolecular physiological ligand is employed, rather than a fortuitous or simplified carbohydrate ligand. Professor Carolyn Bertozzi's research interests span the disciplines of chemistry and biology with an emphasis on studies of cell surface sugars important to human health and disease. Highlights of recent progress include an extension of the list of instances of selectin participation in inflammatory diseases, further definition of selectin carbohydrate specificities, and identification of their carbohydrate-based ligands. However, little is known about how alterations in O-GlcNAc cycling affect human embryonic stem cell (hESC) neural differentiation. Mckl, L. n., Pedram, K. n., Roy, A. R., Krishnan, V. n., Gustavsson, A. K., Dorigo, O. n., Bertozzi, C. R., Moerner, W. E. The Phosphoinositide Kinase PIKfyve Promotes Cathepsin-S-Mediated Major Histocompatibility Complex Class II Antigen Presentation. Bertozzi remains a part of the advisory board for the biologics sector of the company. 275, 21075-21080). Bioaerosol volume collection was estimated at 2.3nL (IQR: 1.1-3.6) for RASC-2 compared with 0.08nL (IQR: 0.05-0.10) for RASC-1 (p<0.0001). The competitive inhibitors 2-bromopalmitate and 2-hydroxymyristate prevented incorporation of omega-alkynyl-palmitate and omega-alkynyl-myristate into palmitoylated and myristoylated proteins, respectively. During Bertozzi's third year of graduate school, Bednarski was diagnosed with colon cancer, which resulted in him taking a leave of absence and changing his career path by enrolling in medical school. We characterized several proteins in LBC phagosomes that change in abundance on induction of autophagy, a process that has been previously implicated in the host defense against microbial pathogens. Laureates [3] [ edit] Laureates per country [ edit] Carolyn Bertozzi is a chemist who has made important contributions to understanding how cells interact. A Pictet-Spengler ligation for protein chemical modification. Baker Family Director of Stanford ChEM-H, Anne T. and Robert M. Bass Professor in the School of Humanities and Sciences and Professor, by courtesy, of Chemical and Systems Biology and of Radiology, AB, Harvard University, Chemistry (1988). The apparent rate constants for the hydrolysis and disappearance of the cell surface conjugates were determined, as well as the apparent rate constant for the formation of covalent bonds with cell surface ketones. Precision glycocalyx editing as a strategy for cancer immunotherapy. Cell surface sialosides constitute a central axis of immune modulation that is exploited by tumors to evade both innate and adaptive immune destruction. Herein, we report the first application of this glycoproteomic platform to human tissues cultured exvivo. To address this deficiency, chemists have developed technologies to perturb glycan biosynthesis, profile their presentation at the systems level, and perceive their spatial distribution. This function deteriorates during ageing and neurodegenerative disease, concomitant with cognitive decline. We demonstrate binding of all three selectins to GlyCAM-1 and demonstrate that the binding interactions satisfy a number of important criteria. Under these conditions, Nrf1 is inactive in regulating proteasome subunit gene expression in response to proteasome inhibition. An essential step in this pathway is the activation of sulfate through adenylation by the enzyme ATP sulfurylase (ATPS), forming adenosine 5'-phosphosulfate (APS). Conversely, unsialylated LacNAc glycans, enriched in the epithelial ducts, sequestered Gal-1 in the extracellular environment, ultimately attenuating invasive potential. With the aid of density functional theory calculations reported previously by Nagano and co-workers, we identified azidofluorescein derivatives that were predicted to undergo an increase in fluorescence quantum yield upon Cu-catalyzed or Cu-free cycloaddition with linear or cyclic alkynes, respectively. Carroll, K. S., Gao, H., Chen, H. Y., Leary, J. [38] Redwood Bioscience is a biotechnology company that uses SMARTag, a site-specific protein modification technology that allows small drugs to attach to sites on the proteins and can be used to help fight cancers. The Staudinger ligation with alkyl azides was second-order overall and proceeded more rapidly in polar, protic solvents. However, a direct role for SL-1 in M. tuberculosis virulence has not been established. View details for Web of Science ID 000257236600029, View details for PubMedCentralID PMC2667816, View details for DOI 10.1002/anie.200704847, View details for Web of Science ID 000254379500008, View details for PubMedCentralID PMC2446402, View details for DOI 10.1002/anie.200802525, View details for Web of Science ID 000260622700027, View details for PubMedCentralID PMC2748828. [43], In 2017, Bertozzi helped found InterVenn Biosciences, which uses mass spectrometry and artificial intelligence to enhance glycoproteomics for target and biomarker discovery, ovarian cancer diagnostics, and predicting the successes and failures of clinical trials. The purified enzyme catalyzed the sequential esterification of trehalose with two palmitoyl groups, generating a diacylated product similar to the 2,3-diacyltrehalose glycolipids of M. tuberculosis. Multicellular organs comprise differentiated cell types with discrete yet interdependent functions. Metabolic incorporation of d-alanine derivatives and click chemistry detection constitute a facile, modular platform that facilitates unprecedented spatial and temporal resolution of PG dynamics in vivo. The method was applied to assay for the heparin substrate specificity of a newly discovered human extracellular endosulfatase, HSulf-2, which has been implicated in tumorigenesis. View details for Web of Science ID 000310103800025, View details for PubMedCentralID PMC3596100. Professor Carolyn Bertozzi won the 2022 Nobel Prize in Chemistry for a technique she developed to look at tiny strands of sugar on the surface of our cells. 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. Mucin glycoproteins contribute to a wide range of cell-surface phenomena. Tuberculosis (TB) is the leading cause of death from an infectious bacterial disease. View details for Web of Science ID 000250260500015. Using this approach quantities of homogeneous material were obtained for structural and functional analysis. In addition, the general assay architecture should be readily applicable to high-throughput screens of other carbohydrate sulfotransferases. ppGalNAc T1 and T2 revealed no significant enhancements suggesting Ser/Thr-O-GalNAc was inhibitory at most positions for these isoforms. Second messengers generated by Fc receptors activated integrins, which formed an actin-tethered diffusion barrier that excluded CD45. Phagocytosis is the central process by which macrophage cells internalize and eliminate infectious microbes as well as apoptotic cells. Yet, a mechanistic understanding of how O-GlcNAc functions in T cell activation remains elusive, partly because of the difficulties in mapping and quantifying O-GlcNAc sites. Targets intended for clearance expose ligands that initiate their phagocytosis ("eat me" signals), while others avoid phagocytosis by displaying inhibitory ligands ("don't eat me" signals). We applied this "azido-ELISA" to the family of polypeptide alpha-N-acetylgalactosaminyltransferases (ppGalNAcTs), all of which were able to transfer N-azidoacetylgalactosamine (GalNAz) from the unnatural nucleotide sugar donor UDP-GalNAz. 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. We anticipate that this chemical method will find broad use in epigenetics to enable unbiased searches for new PKMT substrates by using recombinant enzymes and unnatural SAM cofactors to label and purify many substrates simultaneously from complex organelle or cell extracts. 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. Identification of ManNAc 6-kinase as a bottleneck for unnatural sialic acid biosynthesis provides a target for expanding the metabolic promiscuity of mammalian cells. Chandra, R. A., Douglas, E. S., Mathies, R. A., Bertozzi, C. R., Francis, M. B. View details for DOI 10.1016/j.bmcl.2011.05.045, View details for Web of Science ID 000293884100002, View details for PubMedCentralID PMC3341932. N610 was also the primary site of sialylation of the receptor. View details for Web of Science ID 000259675500001, View details for PubMedCentralID PMC2709988. One of the most fundamental queries is the extent to which the combinations of DNA-, RNA- and PTM-level variations explode the complexity of the human proteome. Czlapinski, J. L., Schelle, M. W., Miller, L. W., Laughlin, S. T., Kohler, J. J., Cornish, V. W., Bertozzi, C. R. Structural Characterization of a Novel Sulfated Menaquinone produced by stf3 from Mycobacterium tuberculosis. Application of the IsoTaG platform to 15 cell lines metabolically labeled with Ac4GalNAz or Ac4ManNAz revealed 1375 N- and 2159 O-glycopeptides, variously modified with 74 discrete glycan structures. Despite its relevance in both health and disease, studies of the glycocalyx remain hampered by a paucity of methods to spatially classify its components. She coined the term bioorthogonal chemistry to Using a multicolor detection strategy, we performed a spatiotemporal analysis of glycan expression and trafficking and identified patterns that would be undetectable with conventional molecular imaging approaches. Although this phenomenon is well-established, little is known about the molecular-level interactions on which it depends. The quadricyclane ligation joins a small but growing list of tools for the selective covalent modification of biomolecules. A key tool in this study is the Staudinger ligation, a highly selective reaction between modified triarylphosphines and azides that produces an amide-linked product. Perez-Vilar, J., Mabolo, R., McVaugh, C. T., Bertozzi, C. R., Boucher, R. C. Molecular basis for G protein control of the prokaryotic ATP sulfurylase. Bowman, K. G., Hemmerich, S., Bhakta, S., SINGER, M. S., Bistrup, A., ROSEN, S. D., Bertozzi, C. R. Chemical approaches to glycobiology and emerging carbohydrate-based therapeutic agents, A strategy for the chemoselective synthesis of O-linked glycopeptides with native sugar-peptide linkages. 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. Here, we sought to define if uncharacterized sialidases would provide distinct paradigms in sialic acid biochemistry. Our results indicate that, unlike UDP-GlcNAc 2-epimerase, which promotes biosynthesis of sialic acid, GlcNAc 2-epimerase can serve a catabolic role, diverting metabolic flux away from the sialic acid pathway. Technologies for introducing molecules into living cells are vital for probing the physical properties and biochemical interactions that govern the cell's behavior. PAPS is also the substrate for sulfotransferases that produce sulfolipids, putative virulence factors, in Mycobacterium tuberculosis such as SL-1. Carolyn R. Bertozzi, in full Carolyn Ruth Bertozzi, (born October 10, 1966, Boston, Massachusetts), American chemist known for her application of chemical synthesis to the study of biological systems. The FGE recognition sequence, or aldehyde tag, can be inserted into heterologous recombinant proteins produced in either prokaryotic or eukaryotic expression systems. The difference in preferred substrates between L-selectin and MECA-79 may explain the variable activity of MECA-79 as an inhibitor of lymphocyte adhesion to high endothelial venules in lymphoid organs. These results have highlighted the need for additional imaging probes. These challenges have motivated the development of chemoselective ligation, the selective covalent coupling of mutually and uniquely reactive functional groups under mild, aqueous conditions. Therefore, sulfation may increase the estrogenic potential of xenobiotics. Tuberculosis (TB) disease is a global epidemic caused by the pathogenic Mycobacterium tuberculosis (Mtb). View details for DOI 10.1073/pnas.1222041110, View details for Web of Science ID 000322771100029, View details for PubMedCentralID PMC3740907. CalFluors: A Universal Motif for Fluorogenic Azide Probes across the Visible Spectrum. The enrichment method is based on covalent capture of azide-containing peptides by the azide-reactive cyclooctyne (ARCO) resin and is demonstrated for two different applications. The ketone group within the levulinoyl side chain of SiaLev was then used as a chemical handle for detection using a biotin probe. Circumventing the steps of purification from native cell membranes, this methodology facilitates the reconstitution of membrane-associated proteins. Reconstitution of membrane-associated proteins and may be more informative than steady-state analyses the aging brain a number of important.... Of immune modulation that is exploited by tumors to evade both innate and adaptive immune destruction proinflammatory in... R. A., Douglas, E. S., Mathies, R. A. bertozzi. Tuberculosis ( TB ) is the leading cause of death from an infectious bacterial disease glycoproteomic to... 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