Harland, C. W., Botyanszki, Z., Rabuka, D., Bertozzi, C. R., Parthasarathy, R. Crosslinking Studies of Protein-Protein Interactions in Nonribosomal Peptide Biosynthesis. We previously synthesized a series of GPI anchor analogs with systematic deletions within the glycan core and coupled them to the GFP by a combination of expressed protein ligation and native chemical ligation [Paulick MG, Wise AR, Forstner MB, Groves JT, Bertozzi CR (2007) J Am Chem Soc 129:11543-11550]. Heineken Prize for Biochemistry and Biophysics (2022); Wolf Prize (2022); AAAS Lifetime Mentor Award (2022); Presidents Innovator Award, Society for Glycobiology (2020); Nagoya Medal (2020); The Chemistry of the Future Solvay Prize (2020); NAS John J. Carty Award (2020); Glenn T. Seaborg Medal, UCLA (2020); F.A. Here we report the in vitro activity of the four GlcNAc-6-sulfotransferases on a panel of synthetic oligosaccharide substrates that comprise structural motifs derived from sialyl Lewis x. Gas-phase stability of the 4Fe-4S cluster was investigated using both in-source and collision induced dissociation, which provided information regarding the relative gas-phase binding strength of iron towards protein ligands and inorganic sulfides. Strategies to ameliorate GBM tissue tension offer a therapeutic approach to reduce mortality due to GBM. Here we show that MmpL8, a member of a large family of predicted lipid transporters in M. tuberculosis, is required for SL-1 production. Inhibitors of carbohydrate recognition and biosynthesis can reveal the biological functions of the carbohydrate epitope and its cognate receptors. A., Bertozzi, C. R. Cell type-selective secretome profiling in vivo. View details for DOI 10.1073/pnas.1008280107, View details for Web of Science ID 000282003700030, View details for PubMedCentralID PMC2944705. Sensitive detection of multiple islet autoantibodies in type 1 diabetes using small sample volumes by agglutination-PCR. View details for Web of Science ID 000264983800005, View details for PubMedCentralID PMC2709817. Our results reveal that these transferases have unique peptide and glycopeptide preferences demonstrating their substrate diversity and their likely roles ranging from initiating transferases to filling-in transferases. The competitive inhibitors 2-bromopalmitate and 2-hydroxymyristate prevented incorporation of omega-alkynyl-palmitate and omega-alkynyl-myristate into palmitoylated and myristoylated proteins, respectively. View details for DOI 10.1074/jbc.M109.017236, View details for Web of Science ID 000268097400064, View details for PubMedCentralID PMC2740463. View details for DOI 10.1074/jbc.M809088200, View details for Web of Science ID 000265688300019, View details for PubMedCentralID PMC2676004. Cells bend their plasma membranes into highly curved forms to interact with the local environment, but how shape generation is regulated is not fully resolved. The end purpose of the described approaches is the production of glycosylated materials for experiments relevant to the biological investigation of glycoproteins, although the strategies presented apply to other posttranslational modifications as well. 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. Wu, P., Shui, W., Carlson, B. L., Hu, N., Rabuka, D., Lee, J., Bertozzi, C. R. Boron Nitride Nanotubes Are Noncytotoxic and Can Be Functionalized for Interaction with Proteins and Cells. WebIn Bio Eats World's Journal Club episodes, we discuss groundbreaking research articles, why they matter, what new opportunities they present, and how to take these findings from paper to practice. In June 2015, she joined the faculty at Stanford University as an Institute Scholar at Sarafan ChEM-H. Prof. Bertozzi's research interests span the disciplines of chemistry and biology with an emphasis on studies of cell surface glycosylation pertinent to disease states. Here we studied the mechanism of sulfonucleotide reduction by APS reductase from the human pathogen Mycobacterium tuberculosis, using a combination of mass spectrometry and biochemical approaches. The assay is suitable for high-throughout screening of compounds and may find use in the identification of selectin antagonists with anti-inflammatory potential. View details for Web of Science ID 000177297600001. Please refer to the appropriate style manual or other sources if you have any questions. The spatial display of cellular ligands and receptors is important for cell adhesion and communication. The key building block, a pentasaccharide-Asn analogue containing two thiol residues, was incorporated into CD52 by 9-fluorenylmethoxycarbonyl (Fmoc)-based solid-phase peptide synthesis. Methods for the controlled derivatization of glycoproteins are presently limited by the repertoire of natural amino acid side chain and carbohydrate functionalities. Subcellular Partitioning and Intramacrophage Selectivity of Antimicrobial Compounds against Mycobacterium tuberculosis. [12], Carolyn Bertozzi received her A.B. A genome-wide CRISPR screen identifies novel ligands for the Siglec family of glyco-immune checkpoint receptors. In this study we probed the importance of the stem region with respect to substrate preference, localization, and oligomerization. These challenges have motivated the development of chemoselective ligation, the selective covalent coupling of mutually and uniquely reactive functional groups under mild, aqueous conditions. Dinkele, R., Gessner, S., McKerry, A., Leonard, B., Seldon, R., Koch, A. S., Morrow, C., Gqada, M., Kamariza, M., Bertozzi, C. R., Smith, B., McLoud, C., Kamholz, A., Bryden, W., Call, C., Kaplan, G., Mizrahi, V., Wood, R., Warner, D. F. Modulation of immune cell reactivity with cis-binding Siglec agonists. View details for Web of Science ID 000081721100060, View details for Web of Science ID 000080303100023, View details for Web of Science ID 000080212600003, View details for Web of Science ID 000079041700025. The leukocyte adhesion molecule L-selectin mediates lymphocyte homing to secondary lymphoid organs and to certain sites of inflammation. View details for Web of Science ID 000177054900001, View details for Web of Science ID 000175790100030, Here we report a concise stereoselective synthesis of myo-inositol via ring-closing metathesis. This strain-promoted azide-alkyne cycloaddition is often referred to as "Cu-free click chemistry". 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. WebCarolyn R. Bertozzi Benjamin F. Cravatt United States United States United States: for their seminal contributions to understanding the chemistry of cellular communication and inventing chemical methodologies to study the role of carbohydrates, lipids, and proteins in such biological processes. We used this strategy to construct a paracrine signaling network in isolated 3-dimensional microtissues. Comparison of the photoacoustic signal for dansylamide versus standard compounds (ferrocene, tetraphenylethylene, 8-anilinonaphthalene-1-sulfonate, and/or 5,5'-dithiobis(2-nitrobenzoic acid) in 12 different solvents gave fh values (fraction of each absorbed 337.1-nm photon returned as heat) from a low of 0.530 in 1,4-dioxane to a high of 0.973 in water. 56Carolyn Bertozzi 12 Bertozzi won the prize for studying the sugar coats of cells. [27][44], She co-founded Grace Science Foundation in 2018. In contrast, polySia expression and function in the nervous system has been well characterized. The ability to label mucin-type O-linked glycoproteins with chemical tags should facilitate their identification by proteomic strategies. In addition, we generated a mutant M. tuberculosis strain lacking FGE. in these pages has relative advantages and disadvantages. Lin, F. L., van Halbeek, H., Bertozzi, C. R. Synthetic analogues of glycosylphosphatidylinositol-anchored proteins and their behavior in supported lipid bilayers. Wisnovsky, S., Mockl, L., Malaker, S. A., Pedram, K., Hess, G. T., Riley, N. M., Gray, M. A., Smith, B. The data from these experiments suggest that the GPI anchor is more than a simple membrane-anchoring device; it also may prevent transient interactions between the attached protein and the underlying lipid bilayer, thereby permitting rapid diffusion in the bilayer. Chemical biotinylation followed by enrichment and mass spectrometry led to the identification of glycoproteins that were found at elevated levels or uniquely in cancerous prostate tissue. Both the Staudinger ligation and the strain-promoted [3 + 2] cycloaddition using optimized cyclooctynes were effective for tagging azides on live cells. In 2014, it was announced that Bertozzi would lead ACS Central Science, the American Chemical Society's first peer-reviewed open access journal, which offers all content free to the public. Stanford is continually monitoring the status of COVID-19, also called novel coronavirus. This work therefore extends the use of bioorthogonal labeling strategies to problems of clinical relevance. We employed BARAC for live cell fluorescence imaging of azide-labeled glycans. The importance of sulfated molecules in cell-cell communication motivated us to develop a rapid two-step method for identifying these metabolites in microorganisms, particularly in pathogenic mycobacteria. Several anti-tuberculosis drugs target the biogenesis of this complex envelope, but their efficacy is declining due to resistance. The detection yield of viable Mtb improved from 43% (median 2 CFU, range: 1-14) to 95% (median 20.5 DMN-Trehalose positive bacilli, range: 2-155). View details for DOI 10.1074/jbc.M405709200, View details for Web of Science ID 000223791500101, View details for Web of Science ID 000225338800003. View details for DOI 10.1093/glycob/cwi064, View details for Web of Science ID 000230346400006. Genome-scale knockout screens assigned putative functional relevance to the RNA-protein interactions observed by ChIRP-MS. This approach can highlight changes in physiology or environment and may be more informative than steady-state analyses. View details for Web of Science ID 000304129200013, View details for PubMedCentralID PMC3355658. The tremendous selectivity of the transformation should permit its execution within a cell's interior, offering new possibilities for probing intracellular interactions. Shin, S., Comolli, L. R., Tscheliessnig, R., Wang, C., Ki Tae Nam, K. T., Hexemer, A., Siegerist, C. E., De Yoreo, J. J., Bertozzi, C. R. D-Amino Acid Chemical Reporters Reveal Peptidoglycan Dynamics of an Intracellular Pathogen. The foundation focuses on curing NGLY1 deficiency through developing therapeutics that are efficient and inexpensive. Each enzyme preferred a terminal GlcNAc residue, and was impeded by the addition of a beta1,4-linked Gal residue (i.e., terminal LacNAc). Four derivatives were experimentally verified in model reactions, and one, a 4-azidonaphthylfluorescein analogue, was further shown to label alkyne-functionalized proteins in vitro and glycoproteins on cells with excellent selectivity. View details for Web of Science ID 000171962100014. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. Using this knowledge, glycosyltransferase assembly lines have been redesigned for the production of specific glycan structures using protein engineering and chemical approaches. Winans, K. A., King, D. S., Rao, V. R., Bertozzi, C. R. Engineering novel cell surface receptors for virus-mediated gene transfer. The complex and diverse structures of GPI anchors suggest a rich spectrum of biological functions, but few have been confirmed experimentally because of the lack of appropriate techniques that allow for structural perturbation in a cellular context. A., Hellman, U., Chen, X., Bertozzi, C. R., Campetella, O. Real-Time Bioluminescence Imaging of Glycans on Live Cells. By mutating catalytic residues of two such enzymes, we engineered mucin-selective binding agents with retained glycoform preferences. WebBecoming a Wolf Prize laureate has been viewed as a potential precursor to receiving the Nobel Prize. 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). Alterations in GalNAc-Ts expression were shown to provide huge variability in the O-glycoproteome in various pathologies, including cancer. ESI-FTICR MS was utilized to characterize a 4Fe-4S containing protein Mycobacterium tuberculosis APS reductase. Characterization of the metabolic fates of four TreAz analogues revealed unique labeling routes that can be harnessed for pathway-targeted investigation of the mycobacterial trehalome. Consistent with this view, increased levels of MMCoA led to increased abundance and mass of both PDIM and SL-1. Inactivation of the conserved steAB genes (cgp_1603-1604) was also found to confer EMB hypersensitivity and cell division defects. Finally, the reaction must be tested in a variety of environments, escalating from aqueous media to biomolecule solutions to cultured cells and, for the most optimized transformations, to live organisms. View details for DOI 10.1073/pnas.0700567104, View details for Web of Science ID 000246599900007, View details for PubMedCentralID PMC1895932. Our results suggest that the shift to host lipid catabolism during infection allows for increased virulence lipid anabolism by the bacterium. 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). A., Krishnan, V., Pett, C., Yu, J., Woods, E. C., Kramer, J. R., Westerlind, U., Dorigo, O., Bertozzi, C. R. CD22 blockade restores homeostatic microglial phagocytosis in ageing brains. Mockl, L., Pedram, K., Roy, A., Krishnan, V., Gustavsson, A., Dorigo, O., Bertozzi, C., Moerner, W. Enzyme toolkit for selective enrichment and analysis of mucin-domain glycoproteins. View details for Web of Science ID 000173696100012. The surface-bound glycopolymers bind lectins in a ligand-specific manner. Thus, choice of enrichment strategy has profound implications on experimental outcomes. WebCarolyn Ruth Bertozzi is an American chemist and Nobel laureate, known for her wide-ranging work spanning both chemistry and biology. and Irmgard Chu Distinguished Professorship in Chemistry, UC Berkeley (2005-14), Agnes Fay Morgan Research Award, Iota Sigma Pi (2004), Fellow, American Association for the Advancement of Science (2002), Irving Sigal Young Investigator Award, Protein Society (2002), Donald Sterling Noyce Prize for Excellence in Undergraduate Teaching, UC Berkeley College of Chemistry (2001), Department of Chemistry Teaching Award, UC Berkeley (2000), Merck Academic Development Program Award, Merck (2000), Presidential Early Career Award in Science and Engineering (PECASE), The U.S. White House (2000), Camille Dreyfus Teacher-Scholar Award, Camille and Henry Dreyfus Foundation (1999), Beckman Young Investigator Award, Arnold and Mabel Beckman Foundation (1998), Glaxo Wellcome Scholar, Glaxo Wellcome (1998), Prytanean Faculty Award, Prytanean Women's Honor Society, UC Berkeley (1998), Research Innovation Award, Research Corporation (1998), Young Investigator Award, Office of Naval Research (1998), Horace S. Isbell Award in Carbohydrate Chemistry, American Chemical Society (1997), New Investigator Award in Pharmacology, Burroughs Wellcome (1997), Sloan Research Fellow, Alfred P. Sloan Foundation (1997), Pew Scholars Award in the Biomedical Sciences, Pew Charitable Trusts (1996), Young Investigator Award, Exxon Education Fund (1996), Dreyfus New Faculty Award, Camille and Henry Dreyfus Foundation (1995), Member, National Academy of Inventors (2013 - Present), Member, Institute of Medicine (2011 - Present), Member, German Academy of Sciences Leopoldina (2008 - Present), Member, National Academy of Sciences (2005 - Present), Member, American Academy of Arts and Sciences (2003 - Present), Chair, Scientific Advisory Board, Redwood Bioscience, Board Member, Board of Scientific Counslors, Broad Institutue, Board Member, Research Advisory Baord, Glaxo Smithkline, AB, Harvard University, Chemistry (1988), Membrane curvature regulates the spatial distribution of bulky glycoproteins. 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