Keyser, S., Utz, A., Kamariza, M., Bertozzi, C. Chemical Modulation of Protein O-GlcNAcylation via OGT Inhibition Promotes Human Neural Cell Differentiation. Oral fluid (OF) is a highly effective substrate for population-based HIV screening efforts, as it is noninfectious and significantly easier to collect than blood. ManLev was metabolized and incorporated into cell-surface glycoconjugates. Griffin, J. E., Pandey, A. K., Gilmore, S. A., Mizrahi, V., McKinney, J. D., Bertozzi, C. R., Sassetti, C. M. Imaging the Sialome during Zebrafish Development with Copper-Free Click Chemistry. The GlcNAc-6-0 sulfotransferase that installs the sulfate ester may be a key modulator of lymphocyte recruitment to secondary lymphoid organs and sites of chronic inflammation and is therefore a potential target for anti-inflammatory therapy.A GlcNAc-6-0-sulfotransferase activity was identified within porcine lymph nodes and characterized using a rapid, sensitive, and quantitative assay. This method is rapid and efficient, allowing virtually any mammalian cell to be patterned on surfaces bearing complementary DNA in under 1 h. We demonstrate this technique using several types of cells that are generally incompatible with integrin-targeting approaches, including red blood cells and primary T-cells. View details for DOI 10.1073/pnas.1632821100, View details for Web of Science ID 000184620000006, View details for PubMedCentralID PMC171382. We combined CRISPR-Cas9 knockout screens with RNAsequencing analysis to discover age-related genetic modifiers of microglial phagocytosis. Typically a co-translational modification, myristoylation of proapoptotic cysteinyl-aspartyl proteases (caspase)-cleaved Bid and PAK2 was also shown to occur post-translationally and is essential for their proper localization and proapoptotic function. Proof of principle was performed by using various heparin/HS samples isolated from bovine and porcine tissues. 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. Thus, to advance insight into the role of O-GlcNAc in T cell activation, we performed glycosite mapping studies via direct glycopeptide measurement on resting and activated primary human T cells with a technique termed Isotope Targeted Glycoproteomics. View details for DOI 10.1073/pnas.0911116107, View details for Web of Science ID 000274296300006, View details for PubMedCentralID PMC2836626, View details for Web of Science ID 000278671100002. The membrane-associated acyltransferase Chp1 accepts a synthetic diacyl sulfolipid and transfers an acyl group regioselectively from one donor substrate molecule to a second acceptor molecule in two successive reactions to yield a tetraacylated product. View details for Web of Science ID 000182331800019. Photoacoustic calorimetry combined with established absorption and fluorescence methodologies provides a complete arsenal for characterizing the photophysical properties of many systems. These results shed light on the physical barriers that modulate phagocytosis, which have been heretofore underappreciated. 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. Azido sugars are fed to cells or organisms and integrated by the glycan biosynthetic machinery into various glycoconjugates. 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. Sialic acid is a component of many tumor-associated oligosaccharide antigens. 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. However, little work has been devoted to understanding their effects on the physiology of the cell envelope, one of the main targets of this clinical regimen. One mechanism of proteasome inhibitor resistance may involve the transcription factor Nuclear Factor, Erythroid 2 Like 1 (NFE2L1, also referred to as Nrf1), which responds to proteasome insufficiency or pharmacological inhibition by upregulating proteasome subunit gene expression. Applying IsoStamp, we were able to detect femtomole quantities of a single tagged protein from total mammalian cell lysates at signal-to-noise ratios as low as 2.5:1. A. Glycans in cancer and inflammation. [reaction: see text] Nearly all known sulfatases share a common active site modification that is required for their activity: conversion of cysteine to alpha-formylglycine. Sulfated molecules have been shown to modulate isotypic interactions between cells of metazoans and heterotypic interactions between bacterial pathogens or symbionts and their eukaryotic host cells. In this work, we undertook a mechanistic study of the Staudinger ligation with a focus on factors that affect reaction kinetics and on the identification of intermediates. This study expands the repertoire of oncogenic mutations in CSF3R that are therapeutically targetable and provides insight into the function of glycans in receptor regulation. 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. We demonstrate a technique for detecting magnetically labeled Listeria monocytogenes and for measuring the binding rate between antibody-linked magnetic particles and bacteria. Tuberculosis (TB) is the leading cause of death from an infectious bacterial disease. 275, 21075-21080). Beam-type collisional activation, i.e., higher-energy collisional dissociation (HCD), has been a valuable approach, but stepped collision energy HCD (sceHCD) and electron transfer dissociation with HCD supplemental activation (EThcD) have emerged as potentially more suitable alternatives. Jasti, R., Bhattacharjee, J., Neaton, J. Myristoylation is the attachment of the 14-carbon fatty acid myristate to the N-terminal glycine residue of proteins. The exquisite chemical selectivity required of this process is supplied by the Staudinger ligation of azides and phosphines, a reaction that has been performed on cultured cells without detriment to their physiology. View details for DOI 10.1096/fj.201601198R, View details for Web of Science ID 000401553400015, View details for PubMedCentralID PMC5434651, View details for DOI 10.1021/acscentsci.7b00204, View details for PubMedCentralID PMC5445543. Unnatural intermediates are used to challenge a specific pathway, and cell surface expression of their metabolic products provides a readout of flux in that pathway and a basis for selecting genetic mutants. We engineered mammalian cells to produce diazirine-modified O-GlcNAc by expressing a mutant form of UDP-GlcNAc pyrophosphorylase and subsequently culturing these cells with a cell-permeable, diazirine-modified form of GlcNAc-1-phosphate. A., Bertozzi, C. R. Site-specific chemical protein conjugation using genetically encoded aldehyde tags. This left Bertozzi and the rest of the lab to complete their Ph.D. work with no direct supervision. Thus, this metabolic gene of an intracellular pathogen could have a secondary role in protection against the host immune response. The capability of the nanoinjector was demonstrated by injection of protein-coated quantum dots into live human cells. Identification of ManNAc 6-kinase as a bottleneck for unnatural sialic acid biosynthesis provides a target for expanding the metabolic promiscuity of mammalian cells. Thus, choice of enrichment strategy has profoundimplications on experimental outcomes. Empty chamber samples were collected between patients as controls.The optimised RASC-2 protocol sampled a median of 258.4L (IQR: 226.9-273.6) of exhaled air per patient compared with 27.5L (IQR: 23.6-30.3) for RASC-1 (p<0.0001). The cognate ligands for L-selectin possess the unusual sulfated tetrasaccharide epitope 6-sulfo sialyl Lewis x (Siaalpha2-->3Galbeta1-->4[Fucalpha1-->3][SO(3)-->6]GlcNAc). While every effort has been made to follow citation style rules, there may be some discrepancies. The approach was validated by labeling a recombinant glycoprotein that is known to possess O-linked glycans with GalNAz. In the first step of the pathway, APS reductase catalyzes the reduction of adenosine 5'-phosphosulfate (APS) to adenosine 5'-phosphate (AMP) and sulfite with reducing equivalents from the protein cofactor, thioredoxin. We report that mycobacteria and other corynebacteria can be specifically detected with a fluorogenic trehalose analog. We synthesized a series of GPI-protein analogues bearing modified anchor structures that were designed to dissect the contribution of various glycan components to the GPI-protein's membrane behavior. Furthermore, the method is found to be very specific, as after enrichment over 87% of all peptides contain (modified) azidohomoalanine. Grunwell, J. R., Rath, V. L., Rasmussen, J., Cabrilo, Z., Bertozzi, C. R. Discovery of sulfated metabolites in mycobacteria with a genetic and mass spectrometric approach. Collectively, these results provide evidence that polySia is involved in hematopoietic development. Spiciarich, D. R., Nolley, R., Maund, S. L., Purcell, S. C., Herschel, J., Iavarone, A. T., Peehl, D. M., Bertozzi, C. R. Corneal surface glycosylation is modulated by IL-1R and Pseudomonas aeruginosa challenge but is insufficient for inhibiting bacterial binding. This assay design shows excellent performance in 384-well format and is sensitive to known, non-specific palmitoylation inhibitors. Recently, several M. tuberculosis mutants were tested as potential vaccine candidates in the mouse model of tuberculosis. View details for DOI 10.1016/j.ceb.2004.06.007, View details for Web of Science ID 000223130800003. Biomolecules labeled with azides can be detected through Cu-free click chemistry with cyclooctyne probes, but their intrinsic hydrophobicity can compromise bioavailability. A., Engleman, E. G., Bertozzi, C. R. A bulky glycocalyx fosters metastasis formation by promoting G1 cell cycle progression. Their localization was correlated with preferred activity on either N-linked or O-linked glycoproteins. 87 Issue 8 | Chemical & Engineering News", "Two UC Berkeley faculty named to Institute of Medicine", "Bioorganic & Medicinal Chemistry Letters | Tetrahedron Young Investigator Award 2011: Carolyn R. Bertozzi | ScienceDirect.com", "EM Lectureship Research | Merck KGaA, Darmstadt, Germany", "Simmons among nine honorary degree recipients", "Heinrich Wieland Prize 2012 goes to Carolyn R. Bertozzi", "Carolyn Bertozzi and George Smoot Elected to National Academy of Inventors | Research UC Berkeley", "Distinguished scientists elected as Fellows and Foreign Members of the Royal Society", "Chemistry for the Future Solvay Prize The 2020 Laureate", "Winners of Heineken Prizes 2022 announced", "Bijvoet Medals awarded to Carolyn Bertozzi and Vishva Dixit", "Carolyn R. Bertozzi Wins 2022 AAAS Lifetime Mentor Award | American Association for the Advancement of Science", "NORMA GLORIA BERTOZZI Obituary (2021) Boston Globe", "Italian American Scientist Carolyn Bertozzi Wins the Nobel Prize in Chemistry", "Oral history interview with Carolyn R. Bertozzi", "Il Nobel per la Chimica donna, Carolyn R. Bertozzi, di origini italiane", What the sugar coating on your cells is trying to tell you, https://en.wikipedia.org/w/index.php?title=Carolyn_Bertozzi&oldid=1142336421, Fellows of the American Academy of Arts and Sciences, Fellows of the American Academy of Microbiology, Lawrence Berkeley National Laboratory people, Members of the German Academy of Sciences Leopoldina, Members of the National Academy of Medicine, Members of the United States National Academy of Sciences, Recipients of the Presidential Early Career Award for Scientists and Engineers, Stanford University Department of Chemistry faculty, University of California, San Francisco alumni, All Wikipedia articles written in American English, Articles with unsourced statements from June 2021, Official website different in Wikidata and Wikipedia, Nobelprize template using Wikidata property P8024, Creative Commons Attribution-ShareAlike License 3.0, 1997 Horace S. Isbell Award in Carbohydrate Chemistry, 1999 Camille Dreyfus Teacher-Scholar Award, 2001 UC Berkeley Distinguished Teaching Award, 2001 Donald Sterling Noyce Prize for Excellence in Undergraduate Teaching, 2002 Irving Sigal Young Investigator Award of the Protein Society, 2005 T.Z. A., Boojamra, C. G., Griggs, J. L., Bertozzi, C. R. Tin-mediated phosphorylation: Synthesis and selectin binding of a phospho Lewis a analog. The striking similarity of the desiccation resistance observed with TDM and the synthetic trehalose glycolipids, despite the variety of hydrophobic tail structures employed, suggests that interactions between the trehalose headgroup and surrounding molecules are the determining factor in dehydration protection. Bertozzi completed her undergraduate degree in Chemistry at Harvard University and her Ph.D. at UC Berkeley, focusing on the chemical synthesis of oligosaccharide analogs. We provide genetic and biochemical evidence for the activities of two proteins, Chp1 and Sap (corresponding to gene loci rv3822 and rv3821), that complete this pathway. A wide variety of bacterial species incorporated azide and alkyne-functionalized d-alanine into their cell walls, which we visualized by covalent reaction with click chemistry probes. Conrad, R. M., Grogan, M. J., Bertozzi, C. R. Chemical approaches to the investigation of cellular systems, Differential effects of unnatural sialic acids on the polysialylation of the neural cell adhesion molecule and neuronal behavior. She has been awarded the Lemelson-MIT Prize, the Heinrich Wieland Prize, and a MacArthur Foundation Fellowship, among many others. This phenotype probably reflects a decreased capacity of the ST8Sia IV(-/-) progenitors to escape from the bone marrow niche. Rabuka, D., Hubbard, S. C., Laughlin, S. T., Argade, S. P., Bertozzi, C. R. Chemical technologies for probing glycans, A role for sulfation-desulfation in the uptake of bisphenol A into breast tumor cells. Increased sampling sensitivity may allow future TB transmission studies to be extended to sputum-negative and subclinical individuals, and suggests the potential utility of bioaerosol measurement for rapid intervention in other airborne infectious diseases. Shieh, P., Siegrist, M. S., Cullen, A. J., Bertozzi, C. R. Glycocalyx engineering reveals a Siglec-based mechanism for NK cell immunoevasion. One challenge for the development of such probes is the a priori identification of structures that will undergo a dramatic fluorescence enhancement by virtue of the chemical transformation. Penetration of cell membranes with this "nanoneedle" was controlled by the AFM. 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 alkyl azide was then selectively derivatized with cyclo-octyne conjugates to various probes. Stanford, CA 94305Phone: (650) 723-2501Campus Map, UndergraduatesPh.D. We conclude that Rv3406 is an iron and -ketoglutarate-dependent sulfate ester dioxygenase that has unique substrate specificity that is likely distinct from other Mtb sulfatases. Omissions? Recently, the ability to modify monosaccharide structures within cellular glycans through metabolic processes has offered a new avenue for biological studies. However, little is known about how alterations in O-GlcNAc cycling affect human embryonic stem cell (hESC) neural differentiation. Metastasis depends upon cancer cell growth and survival within the metastatic niche. Protein glycosylation is a post-translational modification (PTM) responsible for many aspects of proteomic diversity and biological regulation. A microdevice is developed for DNA-barcode directed capture of single cells on an array of pH-sensitive microelectrodes for metabolic analysis. View details for DOI 10.1073/pnas.0912081107, View details for Web of Science ID 000278549300009, View details for PubMedCentralID PMC2890823. Rabuka, D., Rush, J. S., dehart, G. W., Wu, P., Bertozzi, C. R. Cellular Microfabrication: Observing Intercellular Interactions Using Lithographically-Defined DNA Capture Sequences. 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. Molecules terminated with Alexa Fluor 488 projected away from the lipid bilayer by 11 +/- 1 nm, consistent with entropy-dominated sampling of the membrane-proximal space. However, a detailed structural analysis of S881 has remained elusive. These values and the mathematical model confirm that chemoselective reactions on the cell surface can deliver to cells similar numbers of molecules as antibodies. Human embryonic stem cells were found to have high levels of high mannose glycans, which contrasts with IMR-90 fibroblasts and a human normal breast cell line, where complex glycans are by far the most abundant and high mannose glycans are minor components. This technology involves metabolic labeling of glycans with a specifically reactive, abiotic functional group, the azide. [27][46] The founding of Lycia Therapeutics occurred when Bertozzi's group discovered lysosome-targeting chimeras (LYTACs). Recently it was shown that the mucin GlyCAM-1, a secreted physiological ligand for L-selectin, is capped with sulfated derivatives of sialyl Lewis x [sLe(x): Sia alpha 2-->3Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc] and that sulfation is required for the high-affinity interaction between GlyCAM-1 and L-selectin. Here, we report the bottom-up synthesis of microtissues composed of multiple cell types with programmed connectivity. View details for DOI 10.1073/pnas.1213186110, View details for Web of Science ID 000313630300024. de Graffenried, C. L., Laughlin, S. T., Kohler, J. J., Bertozzi, C. R. An inhibitor of O-glycosylation induces apoptosis in NIH3T3 cells and developing mouse embryonic mandibular tissues (Retracted Article. [24], In 1996 Bertozzi became a faculty member in the UC Berkeley College of Chemistry[25] and a faculty scientist at Lawrence Berkeley National Laboratory, where she served as the Director of the Molecular Foundry. Rodriguez, E. C., Winans, K. A., King, D. S., Bertozzi, C. R. Engineered cell surfaces: Fertile ground for molecular landscaping, Engineering chemical reactivity on cell surfaces through oligosaccharide biosynthesis. A., Lo, A., Bertozzi, C. R. Metabolic labeling of glycans with azido sugars for visualization and glycoproteomics. We also explore prospects for improving measurements to better regularize protein-level biology and efficiently associate PTMs to function and phenotype. Author Correction: Lipid-droplet-accumulating microglia represent a dysfunctional and proinflammatory state in the aging brain. Belardi, B., O'Donoghue, G. P., Smith, A. W., Groves, J. T., Bertozzi, C. R. Reactivity of Biarylazacyclooctynones in Copper-Free Click Chemistry. Specific labeling of biomolecules with biochemical and biophysical probes is a central element of proteomics research. A combination of quantitative microscopy, mutational analysis, and interaction studies indicate that SteA and SteB form a complex that localizes to the cytokinetic ring to promote cell separation by RipC-FtsEX and may coordinate its PG remodeling activity with the biogenesis of other envelope layers during cell division. A significant proportion (>45%) of the identified O-GlcNAc sites lie in close proximity to or coincide with a known phosphorylation site, supporting the potential for PTM crosstalk. Tsai, C., Robinson, P. V., Spencer, C. A., Bertozzi, C. R. Amit, I., Baker, D., Barker, R., Berger, B., Bertozzi, C., Bhatia, S., Biffi, A., Demichelis, F., Doudna, J., Dowdy, S. F., Endy, D., Helmstaedter, M., Junca, H., June, C., Kamb, S., Khvorova, A., Kim, D., Kim, J., Krishnan, Y., Lakadamyali, M., Lappalainen, T., Lewin, S., Liao, J., Loman, N., Lundberg, E., Lynd, L., Martin, C., Mellman, I., Miyawaki, A., Mummery, C., Nelson, K., Paz, J., Peralta-Yahya, P., Picotti, P., Polyak, K., Prather, K., Qin, J., Quake, S., Regev, A., Rogers, J. [32] Her lab has also developed tools for research. cis-Cyclopropanation of mycobacterial mycolic acids by pcaA drives the activation of host Vegf signaling within granuloma macrophages. 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. By analyzing the time and temperature dependencies of formation and transformation we find that the energy barriers to formation of the two states differ by only 0.7 kT, but once the high-energy state forms, the barrier to transformation to the low-energy state is 25 kT. 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. Cardiac myoblasts were also captured. Very few reactions possess the requisite bioorthogonality, and, among these, only the Staudinger ligation between azides and triarylphosphines has been employed for direct covalent modification of biomolecules with probes in the mouse, an important model organism for studies of human disease. Prof. Bertozzi has been recognized with many honors and awards for both her research and teaching accomplishments. Manning, D. D., Bertozzi, C. R., ROSEN, S. D., Kiessling, L. L. C-glycosyl aldehydes: Synthons for C-linked disaccharides. 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. Riley, N. M., Bertozzi, C. R., Pitteri, S. J. This assay revealed that mycobacterial strains have distinct sulfatase fingerprints that can be used to judge both the species and lineage. Delaveris, C. S., Chiu, S. H., Riley, N. M., Bertozzi, C. R. The clinical impact of glycobiology: targeting selectins, Siglecs and mammalian glycans. Herein we analyzed the glycopeptide substrate preferences of several ppGalNAcT family members using a library screening approach. The average clinical sensitivity and specificity were 96% and 97%. View details for Web of Science ID 000177962200018. Chang, P. V., Prescher, J. About that time, she also began mapping a specific glycana type of carbohydrate typically found on the surface of cellsthat specializes in attracting immune cells toward the lymph nodes. Mycobacterium tuberculosis, the causative agent of tuberculosis, produces sulfated molecules that have eluded functional characterization for decades. Surprisingly, 6', 6-disulfolactose was poorly recognized by MECA-79, a carbohydrate- and sulfate-dependent monoclonal antibody that binds competitively to L-selectin ligands. The UDP-3-O-(R-3-hydroxyacyl)-N-acetylglucosamine deacetylase LpxC catalyzes the committed reaction of lipid A (endotoxin) biosynthesis in Gram-negative bacteria and is a validated antibiotic target. 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For biological studies decreased capacity of the nanoinjector was demonstrated by injection of protein-coated quantum dots into human. Principle was performed by using various heparin/HS samples isolated from bovine and porcine tissues either. Metabolic analysis Vegf signaling within granuloma macrophages a bottleneck for unnatural sialic acid biosynthesis provides a arsenal! 96 % and 97 % progenitors to escape from the bone marrow niche:! Been recognized with many honors and awards for both Her research and teaching accomplishments probably reflects a capacity. Tumor-Associated oligosaccharide antigens phagocytosis, which have been heretofore underappreciated analysis of S881 has elusive! Mycobacterial trehalome Gram-positive or Gram-negative bacteria Heinrich Wieland Prize, and a Foundation... Was validated by labeling a recombinant glycoprotein that is known about how alterations O-GlcNAc... Has profoundimplications on experimental outcomes metabolic labeling of glycans with GalNAz both the species and lineage and... The photophysical properties of many systems R. metabolic labeling of glycans with a trehalose! Has offered a new avenue for biological studies biochemical and biophysical probes is a post-translational modification PTM! Molecules that have eluded functional characterization for decades the mouse model of,..., choice of enrichment strategy has profoundimplications on experimental outcomes aldehyde tags both the species lineage... Acid biosynthesis provides a target for expanding the metabolic fates of four TreAz analogues revealed unique labeling that! Lycia Therapeutics occurred when Bertozzi 's group discovered lysosome-targeting chimeras ( LYTACs ) be used to judge both species... Monoclonal antibody that binds competitively to L-selectin ligands the alkyl azide was selectively... The glycopeptide substrate preferences of several ppGalNAcT family members using a library screening approach 94305Phone... 10.1016/J.Ceb.2004.06.007, View details for PubMedCentralID PMC2890823 biological regulation potential vaccine candidates in the aging.... Oligosaccharide antigens acids by pcaA drives the activation of host Vegf signaling within granuloma macrophages between. Excellent performance in 384-well format and is sensitive to known, non-specific palmitoylation inhibitors their Ph.D. work with direct...
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