First, we found that the W37I mutant of LplA catalyzes site-specific ligation of 10-azidodecanoic acid to LAP in cells, in nearly quantitative yield after 30 min. Overall, our findings provide a quantitative characterization of O-GlcNAc glycoproteins and their corresponding modification sites in primary human T cells, which will facilitate mechanistic studies into the function of O-GlcNAc in T cell activation. Mahal, L. K., Charter, N. W., Angata, K., Fukuda, M., Koshland, D. E., Bertozzi, C. R. Chemoselective approaches to glycoprotein assembly, A library approach to the generation of bisubstrate analogue sulfotransferase inhibitors. Their reactive carbonyl groups are typically conjugated with -effect nucleophiles, such as substituted hydrazines and alkoxyamines, to generate hydrazones and oximes, respectively. Laureates [3] [ edit] Laureates per country [ edit] A metabolic labeling approach for glycoproteomic analysis reveals altered glycoprotein expression upon GALNT3 knockdown in ovarian cancer cells. Directed evolution was used to improve the activity of JamB, a membrane-bound bifunctional desaturase/acetylenase. As most therapeutic glycoproteins are sialylated and require this saccharide for optimal pharmacokinetics, we targeted sialic acid as a host for azides using N-azidoacetylmannosamine (ManNAz) as a biosynthetic precursor. Highly reactive cyclooctynes have been sought as substrates for Cu-free cycloaddition reactions with azides in biological systems. She also later developed a click reaction called the strain-promoted alkyne-azide cycloaddition, which, unlike other click reactions involving azides and alkynes, did not require toxic copper ions for the azide to snap together with the alkyne and was highly effective for tracking glycans in live cells. Using ADAP, we detected anti-thyroglobulin autoantibodies from human patient plasma with a 1000-fold increased sensitivity over an FDA-approved radioimmunoassay. IsoTaG is therefore positioned to enhance structural understanding of the glycoproteome. View details for DOI 10.1073/pnas.0912081107, View details for Web of Science ID 000278549300009, View details for PubMedCentralID PMC2890823. Unique chemical functional groups can be delivered to cell-surface glycans by metabolism of the corresponding unnatural precursor sugars. LC-MS/MS mass spectrometry analysis was then performed and the processed data related to the identified glycoproteins show that several hundred proteins are differentially expressed between control and GALNT3 KD A2780s cells. [37], In 2008, Bertozzi founded a startup of her own: Redwood Bioscience also in Emeryville, California. This work suggests that BNNTs may be superior to CNTs for use as biological probes and in biomaterials. Keyser, S., Utz, A., Kamariza, M., Bertozzi, C. Chemical Modulation of Protein O-GlcNAcylation via OGT Inhibition Promotes Human Neural Cell Differentiation. Glycopeptide-bound glycans observed by IsoTaG were found to be comparable to released N-glycans identified by permethylation analysis. Ganesan, L., Shieh, P., Bertozzi, C. R., Levental, I. Isotope-targeted glycoproteomics (IsoTaG) analysis of sialylated N- and O-glycopeptides on an Orbitrap Fusion Tribrid using azido and alkynyl sugars. A., Bertozzi, C. R. Cell type-selective secretome profiling in vivo. Selective protein-protein interactions between nonribosomal peptide synthetase (NRPS) proteins, governed by communication-mediating (COM) domains, are responsible for proper translocation of biosynthetic intermediates to produce the natural product. Pluvinage, J. V., Haney, M. S., Smith, B. H., Sun, J., Iram, T., Bonanno, L., Li, L., Lee, D. P., Morgens, D. W., Yang, A. C., Shuken, S. R., Gate, D., Scott, M., Khatri, P., Luo, J., Bertozzi, C. R., Bassik, M. C., Wyss-Coray, T. The mucin-selective protease StcE enables molecular and functional analysis of human cancer-associated mucins. Nuclear translocation of Gal-1, in turn, was regulated by discrete cell-surface glycans restricted to the front of the mammary end buds. 364 Lomita Drive These data are the first to suggest the feasibility of a strategy that improves the efficiency of gene transfer by using the biosynthetic machinery of the cell to engineer novel sugars on the cell surface. Conversely, ETD-based methods, especially EThcD, are indispensable for site-specific analyses of O-glycopeptides. This nucleotide sugar was readily accepted by fucosyltransferases and provided robust cell-surface labeling of fucosylated glycans, as determined by flow cytometry and confocal microscopy analysis. Our results demonstrate the potential of enzyme-activated probes for rapid pathogen discrimination for infectious diseases. 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. Even though we have only demonstrated its use in visualizing glycans, it can be envisioned that this probe could also be used for bioluminescence imaging of any azide-containing biomolecule, such as proteins and lipids, since azides have been previously incorporated into these molecules. One leads directly to the final low-energy state and the other to the kinetic trap. Discovery and functional interrogation of SARS-CoV-2 RNA-host protein interactions. Screening of the library identified an inhibitor with a K(i) value of 11 microM. Li phin vn-chng si to pan-lan-chhan , ng cho-tet yung phin-si fet-ch khok-chhng kh ke nui-yng. The leukocyte adhesion molecule L-selectin mediates lymphocyte homing to secondary lymphoid organs and to certain sites of inflammation. [4] Bertozzi is also an Investigator at the Howard Hughes Medical Institute (HHMI)[5] and is the former Director of the Molecular Foundry, a nanoscience research center at Lawrence Berkeley National Laboratory. The above reactions, as well as several newcomers with bioorthogonal attributes, have enabled the high-precision chemical modification of biomolecules in vitro, as well as real-time visualization of molecules and processes in cells and live organisms. She is currently a professor of Chemistry, Chemical and Systems Biology, and Radiology at Stanford University, and an Investigator at the Howard Hughes Medical Institute. The glycosylated polymers were end-functionalized with lipid groups and embedded into supported lipid bilayers where they interact with protein receptors in a structure-dependent manner. Here we show that the cytosolic enzyme N-glycanase 1 (NGLY1, the human PNGase) is essential for Nrf1 activation in response to proteasome inhibition. 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. View details for DOI 10.1074/jbc.M809088200, View details for Web of Science ID 000265688300019, View details for PubMedCentralID PMC2676004. We describe a method for modifying proteins site-specifically using a chemoenzymatic bioconjugation approach. We describe a metabolism-based approach to the selection of mutants in glycoconjugate biosynthesis that provides insight into regulatory mechanisms for oligosaccharide expression and metabolic flux. A Fourier transform ion cyclotron resonance mass spectrometer provided accurate mass measurements, and a quadrupole time-of-flight instrument was used to obtain characteristic fragment ions and partial carbohydrate sequences. A., Krishnan, V. n., Pett, C. n., Yu, J. n., Woods, E. C., Kramer, J. R., Westerlind, U. n., Dorigo, O. n., Bertozzi, C. R. Quantitative Super-Resolution Microscopy of the Mammalian Glycocalyx. Cell surface trehalose mycolates are important modulators of mycobacterial pathogenesis and host immune response. Laughlin, S. T., Agard, N. J., Baskin, J. M., Carrico, I. S., Chang, P. V., Ganguli, A. S., Hangauer, M. J., Lo, A., Prescher, J. View details for DOI 10.1073/pnas.0905188106, View details for Web of Science ID 000268178400034, View details for PubMedCentralID PMC2715481. Yu, S., Boyce, M., Wands, A. M., Bond, M. R., Bertozzi, C. R., Kohler, J. J. Elucidation and Chemical Modulation of Sulfolipid-1 Biosynthesis in Mycobacterium tuberculosis. Finally, we found that metabolic labeling of both cell envelope structures reports on drug effects on cell physiology in two hours, far faster than a genetic sensor of cell envelope stress. [2] As of 2022, 12 awardees have subsequently become Nobel laureates; the most recent of those is Carolyn Bertozzi, who received the Nobel Prize the same year. Here, we report a Cu-free variant of click chemistry that can label these biomolecules rapidly and selectively in living systems, overcoming the intrinsic toxicity of the canonical Cu-catalyzed reaction. In the accompanying paper [Hemmerich, S., & Rosen, S.D. Here we describe a coumarin-phosphine dye that undergoes activation of coumarin fluorescence upon Staudinger ligation with azides. A picture emerges of lectin function that is highly sensitive to its organization, which in turn drastically shapes immunity and cancer progression. Dissecting complex cellular processes requires the ability to track biomolecules as they function within their native habitat. This type of enzyme catalyzes the initial step of mucin-type O-glycosylation, that is, the transfer of GalNAc in O-glycosidic linkage to serine and threonine residues in polypeptides. Current approaches offer a precision approaching that of genetic control. Hsiao, S. C., Shum, B. J., Onoe, H., Douglas, E. S., Gartner, Z. J., Mathies, R. A., Bertozzi, C. R., Francis, M. B. Elastomeric high-mineral content hydrogel-hydroxyapatite composites for orthopedic applications. Additionally, we observe enhanced glycocalyx height in response to epithelial-to-mesenchymal transition and to oncogenic KRAS activation. Furthermore, the method is found to be very specific, as after enrichment over 87% of all peptides contain (modified) azidohomoalanine. It is anticipated that the ability of this technique to create virtually any type of 2D heterogeneous cell pattern should prove highly useful for the examination of key questions in cell signaling, including stem cell differentiation and cancer metastasis. A., Bertozzi, C. R. Piperidine-based glycodendrons as protein N-glycan prosthetics. Grogan, M. J., Kaizuka, Y., Conrad, R. M., Groves, J. T., Bertozzi, C. R. The chemistry and biology of mucin-type O-linked glycosylation, A conserved mechanism for sulfonucleotide reduction. She coined the term "bioorthogonal chemistry" for chemical reactions compatible with living systems. We constructed a glycoprotein expression signature, which revealed that metastatic tumours upregulate expression of bulky glycoproteins. 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. View details for Web of Science ID 000167417700020. Here we develop a combined genetic and chemical approach that enables introduction of the diazirine photocrosslinker onto the O-GlcNAc modification in cells. View details for DOI 10.1096/fj.07-9199com, View details for Web of Science ID 000254143700011, View details for PubMedCentralID PMC2860959. She has found a smart way to connect cells together. Exhaled air and bioaerosol volumes were estimated using continuous CO2 monitoring and airborne particle counting, respectively. The sulfate assimilation pathway of Mtb produces a number of sulfur-containing metabolites with important contributions to pathogenesis and survival. The polypeptide N-alpha-acetylgalactosaminyltransferases (ppGalNAcTs) play a key role in mucin-type O-linked glycan biosynthesis by installing the initial GalNAc residue on the protein scaffold. View details for Web of Science ID 000173696100012. Here, we report the development of antibody-sialidase conjugates that enhance tumor cell susceptibility to antibody-dependent cell-mediated cytotoxicity (ADCC) by selective desialylation of the tumor cell glycocalyx. In addition, similar sulfated epitopes are known to be expressed on HEV-like vessels of chronically inflamed tissues; indicating that this sulfotransferase may also contribute to inflammatory lymphocyte recruitment. The obtained data also uncover numerous novel glycoproteins; some of which could represent new potential EOC biomarkers and/or therapeutic targets. A. Sequential assembly of the septal cell envelope prior to V snapping in Corynebacterium glutamicum. 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. Disruption of cysH rendered Mtb auxotrophic for cysteine and methionine, and attenuated virulence in BALB/c and C57BL/6 immunocompetent mice. A key feature of the synthesis was application of an intramolecular aglycon delivery reaction to join two differentially protected glucose monomers, one prepared with a novel alpha-selective glycosylation. Characterizing their peptide and glycopeptide substrate specificity is critical for understanding the biological role and significance of each isoform. Our data show that O-glycopeptides cannot be robustly characterized with HCD-centric methods that are sufficient for N-glycopeptides, and glycoproteomic methods aiming to characterize O-glycopeptides must be constructed accordingly. In 1961, Wittig and Krebs noted that the strained, cyclic alkyne cyclooctyne reacts violently when combined neat with phenyl azide, forming a triazole product by 1,3-dipolar cycloaddition. Conceptual translation of the cDNA sequence reveals a relatively long (i.e. Bioorthogonal chemical reactions, those that do not interact or interfere with biology, have allowed for exploration of numerous biological processes that were previously difficult to study. Cell-surface glycans are attractive targets for molecule imaging due to their reflection of cellular processes associated with development and disease progression. View details for Web of Science ID 000167162100006, View details for Web of Science ID 000166873000031. 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 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. Here we present the first synthetic trehalose glycolipids capable of providing desiccation protection to membranes of which they are constituents. The unsymmetrical (2'-, 3'-, 4'- and 6'-) monodeoxy analogs were synthesized by desymmetrization of alpha,alpha-trehalose and subsequent deoxygenation under radical conditions. To elucidate the important sites of sulfation on Le(x) with respect to L-selectin recognition, we have synthesized six sulfated Le(x) analogs and determined their abilities to block binding of a recombinant L-selectin-Ig chimera to immobilized GlyCAM-1. Recent insights into the domain architecture, localization and regulation of glycosyltransferases have provided a platform for engineering their position within the secretory pathway and access to substrates. There is urgent need for new therapeutic targets and a better understanding of EOC initiation and progression. 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. We employed Tmp-SLF to modulate gene expression in a yeast three-hybrid assay. The ability to chemoselectively monitor H(2)O(2) fluxes in real time in living animals offers opportunities to dissect H(2)O(2)'s disparate contributions to health, aging, and disease. Modulation of PSA expression by chemical means has a role complementary to genetic and biochemical approaches in the study of complex PSA-mediated events. The increase of cell surface sialic acid is a characteristic shared by many tumor types. To identify a tagged-peptide's sequence, we performed an inclusion list-driven shotgun proteomics experiment where peptides bearing a recoded mass envelope were targeted for fragmentation, allowing for direct site mapping. View details for Web of Science ID 000435537701267. 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. PKMTs are likely to have many additional substrates in addition to histones, but relatively few nonhistone substrates have been characterized, and the substrate specificity for many PKMTs has yet to be defined. To our knowledge, this is the first example of a sulfated menaquinone produced in any prokaryote. 1-68A and a 2-dehydroxy analogue, 1-68Aa, inhibit several purified LpxC orthologues. View details for DOI 10.1128/AAC.01639-16, View details for PubMedCentralID PMC5328571. Here, we extend LplA-based labeling to green- and red-emitting fluorophores by employing a two-step targeting scheme. This approach can highlight changes in physiology or environment and may be more informative than steady-state analyses. 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. These findings suggest a mechanism for the selective uptake of BPA into cells expressing estrone sulfatase. Protein glycosylation is widely recognized as a modulator of protein structure, localization, and cell-cell recognition in multicellular systems. The Nobel Prize in Chemistry 2022. View details for Web of Science ID 000252686400026, View details for PubMedCentralID PMC2735189, View details for DOI 10.1002/anie.200705363, View details for Web of Science ID 000257427000014, View details for PubMedCentralID PMC2847391. Through rational design, we redirected a microbial lipoic acid ligase (LplA) to specifically attach an alkyl azide onto an engineered LplA acceptor peptide (LAP). B., Bertozzi, C. R., Pitteri, S. J., Giaccia, A. J., Plevritis, S. K. Toward Point-of-Care Detection of Mycobacterium tuberculosis: A Brighter Solvatochromic Probe Detects Mycobacteria within Minutes. From this global analysis, we have identified a subset of sulfur-metabolizing enzymes that are sensitive to multiple regulatory cues and may be strong candidates for therapeutic intervention. WebDr. B., Carlevaro, G., Araoz, B., Ruiz Diaz, P., Camara, M. d., Buscaglia, C. A., Bossi, M., Yu, H., Chen, X., Bertozzi, C. R., Mucci, J., Campetella, O. Ultrasensitive Antibody Detection by Agglutination-PCR (ADAP). Taken together, these studies indicate that Rv2131c encodes a CysQ enzyme that may play a role in mycobacterial sulfur metabolism. Lastly, DMN-Tre labeled Mtb in TB-positive human sputum samples comparably to auramine staining, suggesting that this operationally simple method may be deployable for TB diagnosis. Incorporation studies using N-acylmannosamine analogues, N-glycolylneuraminic acid, and C-13-labeled N-acetylneuraminic acid. View details for DOI 10.1074/mcp.M111.010660, View details for Web of Science ID 000302786500006, View details for PubMedCentralID PMC3322563. Most cell membrane proteins are known or predicted to be glycosylated in eukaryotic organisms, where surface glycans are essential in many biological processes including cell development and differentiation. In this mechanism, PAPS and trehalose bind and their products are released in random fashion. Ac4GalNAz treatment labeled the surface of healthy mouse corneas, leaving most cells viable, and bacteria preferentially associated with GalNAz-labeled regions. However, disruption of the dimer by mutagenesis did not affect either localization or substrate preference. The incorporation of noncanonical amino acids into recombinant proteins in Escherichia coli can be facilitated by the introduction of new aminoacyl-tRNA synthetase activity into the expression host. A., Bertozzi, C. R. Synthesis of mono- and dideoxygenated alpha,alpha-trehalose analogs. We describe here a screening procedure for the identification of new aminoacyl-tRNA synthetase activity based on the cell surface display of noncanonical amino acids. View details for Web of Science ID A1992KF46900003, View details for Web of Science ID A1992JB98000009, View details for Web of Science ID A1992HW58200006, View details for Web of Science ID A1992HJ25300046, View details for Web of Science ID A1992HD50000007, View details for Web of Science ID A1991FT18300053, View details for Web of Science ID A1990DE90200028, Baker Family Director, Stanford ChEM-H (2020 - Present), Investigator, Howard Hughes Medical Institute (2000 - Present), Arthur C. Cope Award, American Chemical Society (2017), National Academy of Sciences Award in the Chemical Sciences, National Academy of Sciences (2016), Ernest Orlando Lawrence Award, U.S. Department of Energy (2015), Heinrich Wieland Prize, Heinrich Wieland Prize (2012), Lemelson-MIT Prize, Massachusetts Institute of Technology (2010), Ernst Schering Prize, Ernst Schering Research Foundation (2007), Distinguished Teaching Award, UC Berkeley College of Chemistry (2001), Award in Pure Chemistry, American Chemical Society (2001), MacArthur Foundation Genius Award, MacArthur Foundation (1999), Arthur C. Cope Scholar Award, American Chemical Society (1999), Honorary Degree, Freie University Berlin (2014), Honorary Doctorate Degree, Duke University (2014), Hans Bloemendal Award, Radboud Univ. 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. 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